BONUS - Whose career would you rather have?

8 Oct 2025 · 1 h 4 min · 24 chapters

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In short

A themed “career would you rather” tennis debate (plus some tangents) asking which of two players’ careers the hosts would personally prefer, weighing majors, rivals, intangibles, heartbreak, longevity, and even post-retirement involvement.

Guests (hosts/participants)

Catherine (host), David Law (host), Matt Roberts (host), plus live chat participants Vicky and Hannah; Matt and David drive most comparisons. No separate non-host guests are interviewed.

Key claims and notable examples

  • Ash Barty vs Maria Sharapova: Matt prefers Barty for no “question marks” (and avoids Sharapova’s doping-era doubt and Serena head-to-head defining feature); David argues Sharapova’s career-slam completion and French Open wins; others weigh “set completion” vs “intangibles.”
  • Agassi vs Sampras: David and others pick Agassi for winning “the lot” (including Wimbledon 1992) despite Sampras’ longer dominance.
  • Federer vs Nadal: David and Matt pick Federer; David cites Olympic singles gold for Nadal, while Matt emphasizes Federer’s style and domination periods.
  • Serena Williams vs Novak Djokovic: Catherine and David choose Serena for icon status, barrier-breaking, and longevity across eras; others note Djokovic’s satisfaction (Olympic gold, Masters, head-to-head).
  • Steffi Graf vs Martina Navratilova: Martina chosen for rivalry with Chris Evert (43–37) and doubles success with Pam Shriver; discussion includes Graf’s post-retirement distance from tennis.
  • Andy Roddick vs Daniel Medvedev: Roddick chosen for Wimbledon finals vs Federer and Davis Cup commitment; Matt argues Medvedev’s “funny” overachieving career and unique joy.
  • Justine Henin vs Kim Clijsters: Henin chosen for rivalry with Serena and distinctive backhand/power; Clijsters praised for mother comeback (three slams).
  • Other couplets include Borg vs Jimmy Connors (Connors 1991 US Open run), and Anastasia Myskina vs Elena Dementieva (Myskina chosen).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Setting the Stage for Would You Rather

0:46 to 3:40

Discussion of the theme and format for the episode focused on career comparisons of tennis players.

“we talk about it for an hour and it will be an hour tonight because happy Celebrity Traitors Day to all who celebrate which of course includes Matt Roberts.”

Exploring Ash Barty vs. Maria Sharapova

3:41 to 4:56

Debate on whose career is preferable between Ash Barty and Maria Sharapova, touching on their achievements and public perceptions.

“I've got a feeling I'm going to contradict myself a lot tonight.”

Contrasting Agassi and Sampras

4:57 to 12:46

Discussion comparing the careers of Andre Agassi and Pete Sampras, with personal reflections on their legacies.

“And I'm drinking tonight a nighttime tea sent to me by David Law for my birthday.”

Agassi vs. Sampras: A Career Swap?

14:02 to 15:51

The hosts explore whether Agassi would trade his career achievements for Sampras's longevity in Grand Slam victories.

“What do you think Andre Agassi would have swapped from his career to have had the outright lead in the men's Grand Slam race in the way that Pete Sampras did for a long time?”

Federer vs. Nadal: The Ultimate Choice

15:52 to 18:01

The discussion shifts to comparing Federer and Nadal, weighing achievements and playing styles.

“I really thought you were going to love that one.”

Djokovic vs. the Legends

18:02 to 20:46

The hosts debate whether to choose Djokovic's career over Nadal and Federer, considering recent performances and overall impact.

“When it comes down to Nadal against Djokovic, because they've both done everything, yes, then it does have to come down to a maths equation.”

Serena Williams vs. Novak Djokovic

20:47 to 22:41

A lively comparison between Serena Williams and Novak Djokovic, discussing their legacies and achievements in tennis.

“And then maybe this is going to move us on to your one, Catherine, but the Olympics, I don't know.”

Icons of Tennis: The Final Showdown

22:42 to 28:00

The conversation concludes with a debate on the careers of Steffi Graf and Martina Navratilova, including their doubles successes.

“Serena Williams or Novak Djokovic, an inter-gender debate.”

Comparing Doubles Success in Tennis

28:00 to 28:38

Discussion on the significance of doubles success in tennis careers, particularly focusing on Steffi Graf and Martina Navratilova.

“But I do think about that with Serena, you know, like 14-0 in major finals with her sister in doubles.”

Rivalries and Their Impact

28:38 to 30:05

Exploring the importance of rivalries in shaping players' careers, especially the relationship between Navratilova and Chrissie Everett.

“So I was kind of like, oh, Steffi, you're a great career, but you didn't get to win all of that with Pam.”
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Legacy Post-Retirement

30:05 to 32:34

Debate on the importance of a player's contribution to the sport after retirement, contrasting Graf and Agassi's absence with Navratilova's active role.

“and Selish was taken from the sport the way she was, and she had the sport taken away from her, there's that massive what-if there, because there was that period of real dominance from Selish before that stabbing.”

Personal Connections to the Sport

32:34 to 34:58

Discussion on how personal involvement with tennis post-career influences perceptions of players like Steffi Graf and Pete Sampras.

“I just think that is such a significant contribution to the sport.”

Comparing Roddick and Medvedev's Careers

34:58 to 37:03

Analyzing the careers of Andy Roddick and Daniil Medvedev, considering their achievements, playing styles, and public personas.

“And I've often thought the same about Pete Sampras, you know, that he put down his racket and walked away from it and washed his hands of it, basically, and he's got every right to do that.”

Emotional Weight of Major Finals

37:03 to 42:05

Exploring the emotional aspects of major final losses for Roddick and Medvedev, discussing the impact these moments have on their legacies.

“against the greatest grass court player I think I've seen, or certainly one of the two or three in men's tennis in Roger Federer.”

Weighing Medvedev's Unique Career

42:05 to 43:12

Exploring the uniqueness and appeal of Daniil Medvedev's tennis career.

Comparing Justine Henin and Kim Clijsters

43:12 to 45:49

A discussion on the contrasting careers and legacies of Henin and Clijsters.

“I think I know where Matt's going to go with this.”

Crafting the Perfect Backhand Debate

45:49 to 48:08

Debating the aesthetics and effectiveness of backhands in tennis, focusing on Henin and Clijsters.

“Imagine if you were doing a backhand list back then, Matt.”

Deciding Between Borg and Connors

48:08 to 54:32

Weighing the legacies of Borg and Connors based on their achievements and personas.

“Why is that not Gaël Monfils, for instance?”

Closing Thoughts on Tennis Careers

54:32 to 56:00

Final reflections on the importance of joy and achievement in tennis careers.

“I don't want a miserable comeback, Matt.”

Debating Career Achievements: Johansson vs. Dementieva

56:00 to 56:35

The hosts discuss the careers of Thomas Johansson and Elena Dementieva, weighing their achievements.

“I was trying to think of a one to end on.”

The Value of Grand Slams in Careers

56:36 to 57:59

A conversation on the significance of winning Grand Slams versus consistency in tennis careers.

“Like, is, are you okay with having the slam if you're also sort of a bit of a punchline?”

Subjective Choices in Career Preferences

58:00 to 1:00:36

Hosts explore subjective preferences between players with Olympic golds versus those with major titles.

“I thought it was going to be Dementiava.”

Exploring Lesser-Known Players

1:00:37 to 1:02:29

Discussion shifts to players like Nicolas Massoud and Bertic van der Zandschulp, evaluating their careers.

“Would he have been in the mix if we'd have been doing the show beforehand?”

Wrap-Up and Audience Engagement

1:02:30 to 1:03:44

The hosts reflect on the discussion, engage with audience opinions, and highlight upcoming shows.

“But Burtick, he's got funny on his side.”
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Transcript

Automatic transcript. May contain errors.

0:10Hello friends and welcome to the tennis podcast live with you on this lovely Wednesday evening Hello to everybody that is with us live on YouTube. Hello to Vicky and Hannah in the chat. Hello to David Law. Hello, David. Hello. Hello. I'm not only happy to be here, I'm delighted at the topic that seems to have just thrown itself up by somebody and I wasn't ready for it and now I'm really pumped. Yes, this is one of our sort of special, our themed shows where we pick a topic and we talk about it for an hour and it will be an hour tonight because happy Celebrity Traitors Day to all who celebrate which of course includes Matt Roberts.

0:55Hello Matt. I'm right back at you Catherine. Hello yeah what a what a useful use of this hour before Celebrity Traitors. Otherwise I think I'd just be sort of pacing up and down anxiously waiting for it to start so this is this is a great way to spend the evening. How else do you fill the gap between Medford Medvedev against Tien and Celebrity Traitors. Are we recovered collectively? Will we ever be recovered? Are we just counting down to the next time Daniel Medvedev plays Lerner Tien again? Yes, Matt definitely is. Both Matt and I needed a nap afterwards. I don't know what that tells you, but that's what happened.

1:40Yeah, I very much enjoyed Medvedev being asked afterwards whether this is the sort of match that gives him confidence that he managed to get through it. And he just said, no, I'm dead.

1:56I'm going to quote that all the time, just to make, like, awkward, just to make, you know, like general chit-chat awkward when people just say, oh, hi, how are you doing? But no, I'm dead. Matt, what would have happened if celebrity traitors had clashed with Fulham?

2:18Look, it's a good question. That's a horrible question. It's a good question. What? Fulham. I would watch Fulham. Yeah. Okay. No, Sid. Please don't ask me to explain myself, but I would watch Fulham. Because that's not... You can't do that on catch-up. Yeah, like, no chance. You could, but... Yeah, live sport has to trump everything else, I think. Yeah, live sport is always the priority. Yeah. Yeah. Yeah, but celebrity traitors is as close a second. I've got into the spirit of the would you rather, as has just been mentioned. Yes, very good, David. That leads us seamlessly onto our theme for today's show.

3:04Most of our lives are like that, aren't they? I do a lot of that, asking questions like that. Yes, you do, absolutely. Yeah, this is all a very David Law coded show. Today's theme, if you didn't already know, is career, would you rather? So we've got couplets of tennis players. We've come up with some, the barge has very brilliantly come up with many, many submissions, which is excellent. we've got tennis player couplets who have sort of similar careers in terms of like numbers of achievements whose CVs would be on paper comparable but the theme of the debate for us is subjectively whose career of the two we each would rather have so hopefully it'll be sort of interesting tennis debate, but also be kind of revealing of, you know, hidden truths about our personalities, that sort of thing.

4:08You know. Is that the idea? Definitely. Work with me here, folks. I've got a feeling I'm going to contradict myself a lot tonight. Oh, OK. That sounds fun. Yeah, it does sound fun. Just before we get going, I would like to say a big hello. I don't know whether Carrie is with us live tonight. I hope Carrie is either watching or listening at some point. Carrie, who is the owner of current lovely mascot Roger with his big, big paws and former mascot the dearly departed Darwin, sent us the most wonderful letter and care package in the post. Dated June 2025. And it is just coming to me now. I don't know what happened.

4:57But Carrie, it is here. And I'm drinking tonight a nighttime tea sent to me by David Law for my birthday. And drinking it out of the incredible, lovely squirrel mug. Squirrel! That Carrie sent me. And it's the loveliest thing. And I don't know what journey this mug has been on since June of this year. But I'm very grateful to have it now. and it was a very lovely thing to receive. So thank you, Carrie. And please do send Roger content. It is always very welcome. Right. Let's get on to our first tennis career, Would You Rather. Let's start with ours, shall we? Get them out of the way. We've got some excellent, really funny submissions from the barge.

5:45I want to start with Matt's actually, first off. I hope this doesn't ruin Vicky's plans. But I want to start with Maria Sharapova or Ash Barty, because I really loved this one. It really got me thinking. And Matt, seeing as this was your submission, I'm going to let you go first. Whose career would you rather have out of Maria Sharapova or Ash Barty? I just think Sharapova is a really fascinating person to throw into this question, because like completing the career slam is like pretty much the number one tennis achievement in my eyes like the fact that I would even be considering someone who didn't complete the career slam and won fewer slams altogether over Sharapova is just interesting to me and yet very specifically with Sharapova we have the testing positive element and the meldonium of it all and that genuinely changes how I think about Sharapova not that it necessarily sort of to me it doesn't taint her achievements necessarily but the public image the slight what if the general sort of doubting of of whether you believe her or not you know all of that i just think hangs over maria sharapova's career whereas ash barty got in there got shit done like won all the titles she wanted to win won her home slam had her her last moment winning the home slam also got Wimbledon, her dream, and then got out of there and sort of figured out how to enjoy life on tour as much as she was ever going to be able to.

7:41And I just, I end up coming out of it thinking that I'm going, I'm going with Ash Barty because of that very reason, because there's just absolutely no question marks against it whatsoever. She accomplished what she accomplished. Kind of everyone loved her and that was it. and the the only other thing i would i would throw in the way of why i'm going barty over sharapova is the uh sharapova record against serena just like that record against your greatest rival you know who knows maybe if barty played serena that times that number of times she'd have lost that often as well but she didn't have to and therefore she didn't have that record and i just think i just think it's it's a little i just wouldn't want that i just wouldn't want that to be a defining feature of my career that record against my greatest rival so yeah even though someone's won the career slam there I'm going I'm going with the other one and sorry by the way as a real theme of this is going to be I value majors so highly you know and so it's it's surprising to me that I'm going against that here well I which is why I think it's kind of the perfect would you rather because there's so many intangibles in it that can't be quantified in a in a graphic about greatness because that's the whole point of this show right if it was just about weighing up who's got the most major titles the most sort of headline achievements then it's not really a debate is it like this is all bringing it down to the intangibles and the the subjective elements.

9:20And winning a home slam is one of those intangibles, I think. Obviously, that wasn't something that Maria Sharapova ever had available to her. But Ash Barty did and she did it. I think a theme of this show for me is that I'm going to reveal myself as a big career slam person. I am a completist in my personality, to a fault I would say, and I would prize completing the set more highly than pretty much anything else. And I think for that reason I would, in spite of all the other intangibles that are in Ash Barty's favour I think I would go for Maria Sharapova. David what do you think? It is a very interesting one isn't it in terms of we talk about whose career would you rather have we end up coming down to some degree I think with some of these people it may may surface that whose life would you rather have who's which person would you rather be and that's why I think I'll end up probably contradicting myself because I'll give some factual reason for why I'm going for one over the other and then there'll be a similar comparison with two other people just to lay down a rule to try and prevent that i think you're still you okay you're you experiencing their career achievements it's david it's all a stretch yeah okay what i would say is in the ash party scenario you you are also you're you but you're australian so it is it's a home slam for you it's becoming more of a stretch with everything that i say isn't it but you you get the idea well she won when we're done as well right okay you're sure i mean i don't think their their careers are a pretty are particularly comparable really um i think maria sharapova massively you know out uh achieved ash barty really if you line up their careers i think you You rather have.

11:33Oh, Sharapova's. I think you make a solid point about the doping case, Blemish, whatever you want to call it. But I mean, for Maria Sharapova, she won the French Open twice, didn't she? I mean, that is extraordinary, to be honest, for the type of build she is, for the type of player she looked on clay. I would definitely have hers. And as much as Ash Barty was sort of no must, no fuss with her career, Maria Sharapova was very no must, no fuss with her career slam, like five slams overall. But to have done the set, that's very efficient. And I am. I'm all about completing the set. Yeah. I think I think set completion is is going to be quite a significant factor for me, too.

12:28Yeah. I think this is probably the... I think Sharapova is probably the only one where you could offer me someone who hasn't won the career slam against her and I would take it. OK, then. Well, maybe we should come next to Andre Agassi and Pete Sampras. Oh, God. David, this one's supposed to be right up your alley. I know. Somebody put this in last minute and I didn't agree to this. and I really... You're complaining about an Agassi Sampras section of a podcast. Yes, because I spent a whole pre-career life supporting Pete Sampras against Andre Agassi and heralding his victories over him. Technically, he's got more slams.

13:19Because he had an amazing head-to-head against him, because I used to love watching them play each other, and he was better than Agassi. But then when I actually line up their achievements and think that Agassi won them all and he won Olympic gold, I would have had Agassi's career. And I think that, and that stings me to the core to think that. But that is the honest truth. You know, Pete reached the semi-final of the French Open and at times he put everything in. You know, it was a big gap for him and he only got to a semi. I know inverted commas only, but that is a big miss compared to what Agassi did by winning Wimbledon on 92.

14:01I mean, I hated every minute of it, and yet I was in awe of it. And I would go for him. What do you think Andre Agassi would have swapped from his career to have had the outright lead in the men's Grand Slam race in the way that Pete Sampras did for a long time? I don't think he would. Because that is meaningful that he led the way for a long time. I was going to say, if you ask this question in 2000 and, well, any time from 2002 to 2008, do you think the answer would be different with Sampras at the top of the pile there? Because he was so much part of the Federer and Nadal dialogue because he was the target.

14:46It's like how Margaret Court has suddenly become, or from the tail end of Serena's career, how suddenly we were having to talk about Margaret Court all the time because she was the target. An interesting one would have been, would Pete have swapped his achievements for Andre's? That's an interesting question, Mark. What do you think? I don't think he would. I think he loved his total number, and I think more than anything else, he loved his years in a row ending the year world number one. That's what he regards as his biggest achievement, even if historically it's not talked about very often. But I think Agassi wouldn't swap for Pete.

15:30I think he enjoyed his fluctuations. Sampras actually enjoyed his consistency. So I think they're both kind of where they want to be. But in terms of what I would have, I would have Agassi's because I think he knows what it feels like to have won the lot and Pete doesn't. So we're all going Agassi. I thought that might divide the crowd more. It really hurts me. Sorry, David. I can't tell you. I really thought you were going to love that one. What a misfire. OK, let's come into the one that you chose then, David. Roger Federer or Rafael Nadal. What you got? Well, another interesting one, isn't it?

16:14Because Nadal has got more majors on the board and yet I would go for Federer. And this is where I find it quite interesting that I can't just put the numbers up against one another. I can't do it. I have to think of how they did it, you know, and the way Federer won his majors is how I wish I could win them. And, you know, Nadal, it always used to seem like such bloody hard work. I mean, amazing achievement. 14 French Opens I'd rather win more of some of the others but also, god it's too much hard work for my liking I'd love to be able to just swish the ball about I'm not saying that Federer didn't work hard, he did but god, imagine being able to do it like he did it But then, the miracle in Melbourne Yeah 2017 Yeah, I would go for Nadal because of Olympic singles gold, simple as that.

17:19Like that's enough of a, if they had equal everything else. I mean, obviously Nadal's got more slams anyway, but that's not really what swings it for me. It's the Olympic singles gold. I know Federer's got doubles, but so's Nadal. Yeah, that's pretty simple for me, actually. The way they did it doesn't so much factor in. For me. And I also could make a very strong pace of the way. So would you have Djokovic's career then, over the both?

17:54Probably, yeah. So it's just a maths equation, really, in the end. Well, no, not... When it comes down to Nadal against Djokovic, because they've both done everything, yes, then it does have to come down to a maths equation. I mean, my most recent memory of knowing that Djokovic does involve him mopping up his own puke off a court in Shanghai. So I'm going to have to put that out of my brain in order to pick his career just at the moment. But yeah, with those two, that's a pretty unique example where they've done everything. I think you've got to go Djokovic. But with Nadal and Federer, I choose Nadal.

18:33Matt. So your most recent memory of Nadal on court is him losing to Burtick van der Zanskort. More on him later.

18:45I think Federer here as well. I think this is where, you know, I look back on, you know, I spent so long thinking about the Grand Slam race. It took up so much of my brain power in life and it took up so much oxygen. And yet here we are, you know. And this was before it was Matt's job. Oh, for sure. Long before. Yeah, long before. He wasn't getting paid for it to occupy his brain. You know, and yet here we are and, you know, Nadal has two more majors and we're, what, three years, a year on from them retiring. And I don't know, a couple more doesn't feel all that significant to me as I try and split them.

19:33I feel like they both kind of won their race, you know, Federer overtaking Sampras and then Nadal overtaking Federer. Federer's got the most at Wimbledon in the way that Nadal's got the most at Roland Garros and Federer's got the joint most at the US Open so they kind of each own a men's slam I do think Nadal's French Open it feels almost impossible that's ever going to be broken whereas I do think Federer's eight at Wimbledon might be under threat but I do go with David on this and look at just the way Federer played if I could win major titles like that I would very happily have 20 of those if it meant that someone else had 22 and someone else had 24.

20:19I just love the way Federer played. He also, I think, dominated the sport in a way that Nadal didn't. There was a period of total domination where Nadal didn't have that to quite the same extent. Nadal had a lot of injuries in a way that Federer didn't. I could imagine that being a really annoying part of a career, like just constant injuries. And then maybe this is going to move us on to your one, Catherine, but the Olympics, I don't know. I so look at it as an Olympic gold as like an Olympics achievement rather than a sort of tennis one in a way. I kind of just look at Federer's gold in doubles and think, well, he has got a gold medal.

21:10Yeah, well, okay, well, Nadal's got two then. Yeah, but to me that doesn't split them for their careers. I would add more weight to everything else that I've said. I agree with you. An Olympic doubles gold is different to a Grand Slam doubles title, like completely different, but it's not the same. no it's not the same but it's not i think it's less of a deal break singles gold it's less of a deal fair enough okay well my one i mean i i changed mine i sorry just on i think the head-to-head's interesting because i think federer clawed that back a bit in terms of like i know like overall he's been absolutely kind of battered in the head-to-head but federer can look back now and say I'm pretty sure he had a winning record on grass and hard courts at the end of it you know it was the sheer amount of clay court matches that they played against each other where Nadal absolutely owned him of course he did um but I think Federer got a bit of respectability back in that head-to-head in the in that 2017 on period I think I think that was satisfying for Federer to turn that rivalry around against Nadal.

22:30I mean, I feel like I switched up my submission to Agassiz or Sampras, which has ended up putting David in a bad mood. But since you brought up Djokovic, David, why don't we do this one suggested from the Barge? Serena Williams or Novak Djokovic, an inter-gender debate. What do you think? i think serena olympics photos there very very well done vicky for that i think serena david i think serena yeah i do i do i mean listen it's i can understand the argument for for both of course um it's not straightforward but i i just feel like everything I think she came from and to and everything in between, having an elder sister who was already there and dominating the sport and she just overhauls her and just races past everybody in an incredible era of players.

23:35I mean, yes, Djokovic obviously had Nadal and Federer to contend with it, so that is incredible too. But I think that the sheer number of years, is to start with Steffi Graf, move through Ennen and Clysters and Davenport and Capriati and her own sister, and end up battling the generation of today. And a little mention for that Sharapova record as well, despite losing two of the first three, including that Wimbledon heartbreaker. I kind of think that I'd love to know how many Serena might have ended up with had she just not got injured as much as she did. And I just think to win that many over that long.

24:26Well, hang on, if we're doing longevity, Djokovic isn't doing badly on that front. He's still out there in Shanghai puking his guts out at 38. yeah like like to me if we if we're just taking on court factors i i can think of no more satisfying career than novak jokovic's you know most majors most weeks at number one olympics goal most masters head-to-head over federer and nadal multiple wins against nadal at ron garros against federer at Wimbledon some wins against Alcaraz who's 16 years younger than him like on court I do think I do think Djokovic has the edge but it goes back to Catherine's intangibles and for me that that gives Serena the edge you know in terms of just like total icon status breaking barriers just like being the needle.

25:30Get back to me when Novak Djokovic wins a Grand Slam while pregnant. Right. We can re-debate it. I think if you could offer Djokovic the reaction that Serena has when she walks into a room. Yeah. Like any room in the world. Yeah, I don't think Novak Djokovic got sent a... A Life of a Showgirl care package by Taylor Swift this week, did he? So that's another slam dunk for Serena. Yeah, I think four Grand Slam finals post-pregnancy, I think is, this is one of my agendas that I'm always pushing, but I think that's a massively underrated achievement because it's always framed in terms of her not winning them and her not achieving something, but actually to have reached those slam finals post-birth and post-pregnancy and post-very-traumatic birth is absolutely unreal.

26:41And I think Serena is such a champion that that achievement probably doesn't keep her very warm at night. Like, I think she's pretty, you know, trophy or nothing. And I understand that. But I think for me, given that we are getting, we are staying ourselves, but receiving their CVs, I think that would mean quite a lot to me. So yeah, I think I would go Serena. But I do agree with Matt that like, if you're just looking at a career, like it's hard to imagine a more satisfying career in terms of achievement. Even the fact that I know Serena's got more Olympic golds than Djokovic, but like, I don't think Djokovic would swap out the way he finally won that Olympic gold for having done it earlier in his career and got got multiple of them.

27:35I don't think he would swap out last summer's moment in Paris for anything, really. I also think Serena's got, and this is maybe going to come up again later as well in another one, but like all the doubles success with Venus, which I don't know whether that splits it, you know, if it comes down to that. But I do think about that with Serena, you know, like 14-0 in major finals with her sister in doubles. Like that is unbelievable. Yeah. Quite cool. That is one of the coolest things you could possibly have. OK, well then, shall we head to the one I think you just hinted at, Matt, which is pretty fascinating?

28:27Steffi Graf and Martina Novratilova. I'm assuming that's the one that you were hinting at there in terms of what weight to give doubles success. Yes, because what would I want? I'd want to win. loads of majors with Pam Shriver.

28:46So I was kind of like, oh, Steffi, you're a great career, but you didn't get to win all of that with Pam. She won the Golden Slam, Matt. I know, but Pam, you asked what I want. Yeah. I want to be friends with Pam and win a load of doubles with Pam. Yeah. Do we know that Pam isn't friends with Steffi? Maybe. No, but I... She's never mentioned it. She doesn't come up. The calendar golden slam, though. David, what's your answer to this one? It is Martina. And she won four fewer majors. She didn't win that calendar golden slam. but she had the rivalry of all rivalries and she was part of that with Chrissie Everett.

29:46She ended up overhauling it. 43-37 was that rivalry final score. She remains best friends with that rival to this day which I think is incredibly special. She had all the doubles success with Pam as you mentioned And I can't help thinking that because Graf's most remembered rival is Monica Selish, and Selish was taken from the sport the way she was, and she had the sport taken away from her, there's that massive what-if there, because there was that period of real dominance from Selish before that stabbing. and you know I don't think you can ever you can look back on a handful of their matches with great satisfaction Selech and Graf but most of the time you just end up feeling this horrible ache I think because of what it might have been and what it actually was and how sad it was uh and and you don't I don't have that with with Martina and Chrissie Everett I mean obviously there are there are other things that Martina had to deal with in life um but yeah I I and I also again I do come down to how they did it I used to love watching Steffi Graf because she was more she was really dominant when I was becoming an ultra tennis fan but then when I look back on the old footage and see this sir volleying left hander who could just carve people up you know in the way that Martina could I loved that so and also nine Wimbledons by the way still stands nine Wimbledons and I think that that is significant I think the being part of a generation defining rivalry and probably the greatest rivalry of all time.

31:38I think that's a big intangible. Obviously, there's I mean, you won it with Pam, Matt, who is watching live, by the way, and has has messaged in and says, thanks, Matt. Oh, great. So that's I mean, that's that I agree. That's won it won it in itself. But the rivalry thing, I think that's a great point, David, being part of something like that. But both in terms of personal fulfillment and in terms of legacy to the sport, those are the things that really change the sport, I think, more than just racking up numbers, which obviously pretty much everybody here has done. Yeah. And the point that Pam made on our show, you know, our tennis relived with Pam the other day about just how significant Martina and Chrissie were in building the tour.

32:33And, you know, just moving it forward from what Billie Jean King and the original nine had started, you know, like providing kind of the platform for Steffi Graf to achieve what she did. I just think that is such a significant contribution to the sport. A question here, maybe this is getting off topic in terms of debating whose career you'd rather have, but what weight do you give to the legacy that you create post-retirement and the contribution to the sport post-retirement? Because I know Steffi Graf and Andre Agassi have been good luck to them. And they've stayed, I mean, Agassi is very much back on the scene recently.

33:18But for a long, long time, both of them kept themselves themselves. I know they did a lot of charity work where they live in Las Vegas. But in terms of kind of contribution to the sport, they totally, totally stepped away from it. And that remains very much the case for Steffi Graf. like does that whereas Martina is you know she's been in broadcasting and been very much involved in trying to stay relevant and make use of her expertise and legacy um does that is that valid in terms of this debate

34:03somewhat I think I think on the level of like I think it probably means that just as I'm as I'm weighing them up I might be more inclined to go with Martina because frankly she's more front of mind frankly I I do I do think I sort of probably think about her career more than I think about Steffi's but also like I think if I had had a great tennis playing career I would want to keep being part of the sport I do think that would be important to me yes I think it and this is probably unfair I think for me what I do is sort of project onto those decisions like it makes me wonder about how much Steffi Graf really loves tennis, you know, that she was able to just...

34:57That's an important one for me. And I've often thought the same about Pete Sampras, you know, that he put down his racket and walked away from it and washed his hands of it, basically, and he's got every right to do that. Good luck to him. I hope he's happy. But from the outside, that makes me wonder, like... Because thinking about Pam, who we know, like she's desperate just to be involved and give whatever she has to give to the sport yeah um and is so invested in it loves it wants it to be the best it can can possibly be and yeah i this this could be really unfair but that's where my mind goes about players that are able to just walk away from it cold i think steffi and pete had in common that it was a bit of a numbers game.

35:48They loved achievement and success, but they didn't love the sport in quite the way Martina did. I know Andre Agassi, for instance, always talks about how he hated the sport because of his upbringing and so forth. Martina just, she always gives you the feel that, oh, just give me a racket and a ball. Even now, just give me a racket and a ball. I just want to see what I can do with it. and add that to all of her numbers as well. And, you know, the fact that she did want to just keep on playing doubles with Pam all the time and winning all this stuff and it never got old, it never got boring, you know, I think that that is significant.

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36:30Here's a fun one. And it's maybe topical because I think Daniel Medvedev is still in the front of all of our minds. And maybe this is hard because we don't know the end of career achievements of Daniel Medvedev yet. Or maybe we do. But I give you Daniel Medvedev or Andy Roddick. David. Oh, I strongly think Roddick. They're comparable on paper, aren't they, in terms of one slam and a brief stint at number one. Yeah. Three Wimbledon finals for Roddick. against the greatest grass court player I think I've seen, or certainly one of the two or three in men's tennis in Roger Federer. And a US Open final against him.

37:20And a Davis Cup, which I do regard as significant because he threw his whole life into it. You know, he never turned down Davis Cup. Now, it's not Daniel Medvedev's fault that he can't play Davis Cup right now. You know, and he hasn't for a few years. but I do regard that as part of the conversation. Yeah, I feel strongly that... Maybe it's a bit of a heart thing that I used to... I kind of... I like Daniel Medvedev. He's fun and I do... Obviously, he's a really, really good player but his game has never ignited anything in me. His antics are more interesting to me than his game. I think his game is...

38:07If he wasn't fun as a bloke, I would not want to watch him play much. A lot of people would say that Andy Roddick's game maybe left them a bit cold. You know, it was big serve, big forehand, wasn't it? It was explosive. It was really good Steve Johnson. Oh, God, that's... You lost me there. I mean, to me, it's how explosive he was. At the end of his career, yes, I think so. When he started, I think that it was so explosive. Before he lost his forehand, before his arm and his shoulder stopped him being able to hit the forehand he used to hit. I used to love how explosive it was. I'm playing girls' advocate.

38:49I loved it. The fact that Federer could beat him anyway. I always used to talk to Greg Sharko, who was my counterpart on the American side of the ATP tour at the time. He was big and up Roddick, and I was big and up Federer. and it was Roddick who reached world number one first. But I said, look, let's see what happens when they play each other. And I used to love the fact that Federer could just read the guy's serve and just kind of negate it every time. But yeah, I still would go with his. He also got to win a home slam, of course. Again, which isn't something that was ever available to Daniel Medvedev, but that is, it's not nothing.

39:35Even if Mandy Moore is in all of the photos. That'd be quite a funny show, wouldn't it? Not a show, but, you know, a montage. I could make a show out of that, definitely. Matt? Two main points on this. I don't know what it says about the way my mind works, But weighing these two up, I immediately went to which heartbreak would I find easier to handle? Because, you know, they've both got the one major, but I think they're both kind of defined by maybe the major they didn't win. And I think for Medvedev in particular, it is that 2022 Australian Open, where he's in such a great position to beat Nadal and loses.

40:27He was ranting about Nadal today to Mohamed Leani. Yeah, Nadal is clearly living rent-free in Medvedev's head still. But I actually came down on the side that I would find that easier to handle than the Roddick-Wimbledon final against Federer. I think about the volley now. Yeah, I would be up at night thinking about the volley. I wasn't even supporting Roddick in that final, and I still think about the volley. I was going to ask if you were alive. If I played that volley, I would just constantly... Yeah, you'd never think about anything else. It's like that Berrettini backhand against Andy Murray that you still think about.

41:10The other point I would make, just in Medvedev's favour, he stopped Djokovic winning the calendar slam like in his major final win like that's a pretty cool thing to have done like I think I'm biased because Medvedev's just brought me quite a lot of joy over the years and I do think his game is I take David's point like it's you know it's not the most thrilling game but I like that it's kind of funky you know I like that he's got this weird technique and yet he got to world number one and he massively like overachieved no one no one was predicting any of this success for Daniel Medvedev really I don't think whereas I do think you know the fact that you were having that conversation David with Greg Sharka you know Roddick Roddick maybe you know if you if he'd said at the start of his career that he'd only win one major he might look back on that and think but obviously Federer became so good that that was a big obstacle for him but I just think Medvedev I don't know I just think Medvedev's career is pretty cool and like that whole thing of winning he's won loads of different titles he hasn't defended any of them but he's won he's had success in loads of different places I think that's kind of unique and fun and yeah I do think I would get a lot of if Medvedev's career is funny I think I would get a lot of pleasure from having a funny career not like not not one that's sort of one that is funny but also actually good you know world number one and to achieve world number one and Grand Slam title but also be funny that's quite a unique balance isn't it yeah I think I don't know it's pretty iconic to have that forehand and have been a world number one yeah we all need funny yeah god you've made such a compelling case for Medvedev there the weighing up heartbreak is such a because on paper Medvedev's got more heartbreak two Grand Slam final losses from two sets to love up and another loss in five sets right but then the volley the volley yeah At least you can hit a volley most of the time.

43:38Touché, David. Touché. Here's a good one. Let's go to Belgium for a moment. Justine Ennan or Kim Clysters. I think I know where Matt's going to go with this. Do you? Because I really struggled on this. Did you? Well, I think of you as a real Ennan guy. Yeah, I did. I did come down on Ennan. it's because of the back end isn't it let's be honest and that she sort of accidentally guested in the background of a podcast at Roland Garros this year remember that? yeah I do look I think Enin's what she's got three of the four majors, Climster's got two of the four, Enin's got the Olympics gold she's got the tour finals as well you know big kind of really big big titles and she also reached the final of all four majors which which Clijsters didn't do I think the strongest thing in Clijsters' case is her comeback you know like the comeback winning three slams as a mother Jada coming out on court you know it's a really iconic scene I think maybe a more iconic sort of moment than maybe NN ever had but I But I do think Ennan's achievements, the fact that she was only six and eight against Serena, like she really caused Serena trouble.

45:07Like there was genuinely years there where you could say she was Serena's biggest rival, biggest problem. And she was just playing in a way that was kind of unique. And I think Kaisers probably was as well with her incredible sort of athleticism and defense and everything. But yeah, Ennan, it's just such a satisfying game. It maybe goes back to a little bit of what David said earlier about I can't take the way they did it out of it. And the way Ennan did it has just swung it for me on this one. But yeah, Clijsters, epic too. David? Well, the way that Clijsters did it was with joy, which I never felt Ennan had.

45:53I would go for Ennan because of that rivalry that you mentioned with Serena I think at the height I hadn't even looked at the proper numbers on this because I think the rivalry that always stands out to me on behalf of Ennan because she was she doesn't look like all the other champions she was physically nowhere near as big and powerful and yet she generated power wow, imagine having been able to do that with that backhand. Imagine if you were doing a backhand list back then, Matt. Gee, it would have been fascinating. I should have been on it, I think. I mean, it wouldn't have existed because the list was born out of a Samova.

46:37Which is interesting because Matt's not usually as susceptible to the aesthetics of a single-handed backhand as most people in tennis. No. Most people in tennis way over index a single-handed backhand. But I do like a WTA single-handed backhand. Just for the... You're a big Margarita Gasparian guy. Victoria Goljavich was on the original list for a reason. Which is hilarious. She hasn't been on it for a while though, has she? You know, I saw the other day, she's ranked now like 64 in the world. She's coming back. Really? Yeah. How has she done that? I don't know. Getting back to the proper backhand.

47:21Is she the highest-ranked single-hander in... Yeah, she might be again. Diane Parry? She hasn't been winning much. There aren't many around, are there? It's Parry and Golubich, isn't it? I have a feeling that if you'd have done a backhand list back then, you'd have been calling Enam the backhand. And, you know, I do. I mean, everybody did. That face is falling at that suggestion. Go back and watch. I was around for Enam and it didn't move me the same way the Inisimova back can't has moved me. But it's an incredible shot. I think your 10-year-old eyes might have had a slightly different angle on the sport, no?

48:02I think you're under-esiting how much old tennis Matt watches on YouTube, David. Yeah. Fair enough. but listen it's it's I would go in and but but I can definitely again a bit like with Federer I could imagine how great would it be to to win all this stuff and love it and love life and think isn't it easy and fun feels like Glystis has just had more moments more iconic moments and more stories more things that have moved people but I think unquestionably En-An has the better CV so I think I'm going to go for for Ennan and sort of back myself to bring the joy somehow let's go to France for our next one, let's have Joe Wilfred Songer or Richard Gasquet can't believe this is even on it's Songer isn't it, this comes down to joy doesn't it move on I think it also comes down to achievements Tell me, what has Richard Gasquet got any right to be in this conversation for?

49:13Why is that not Gaël Monfils, for instance? Don't come for the barge, David. Well, I mean, really. I'm sorry. Bless him, but Richard Gasquet should not even be on the same photo as Joe Wilfrid Zonga. He has not reached a Grand Slam final. He has not beaten Roger Federer and Novak Djokovic at Grand Slam tournaments. what are we doing quick Vicky Connors or Borg get the pictures up yeah this one's hard okay go on then David do you accept these people being on the same same photo panel together great okay Borg won more Grand Slams he won 11 to Connors 8 Connors had the longevity Borg had the total domination of the French Open and Wimbledon a bit like Federer had at the US Open you know that five in a row it's when I was a kid Borg was just had just won his fifth Wimbledon in a row when I first watched Wimbledon and then when I found out that there was a tournament called the French Open and I kind of got a sense of what that meant and that he'd won six of those in a row at the same time it was just absurd um but he could never win the the us open he never managed to figure it out under the lights um i'm i'm going a massive heart overhead argument that if i was jimmy connor's i would get to experience 1991 us open semi-final run in his skin i'm so glad that came up i knew I would choose that.

50:58I would choose that. I think I would too. Yeah. Vibes. Would you... Yeah. How many... We don't really know Jimmy Connors, do we? But, like, how many Grand Slam titles do you think that is worth to him? That 1991 run, you know? I do think it's worth one. He's remembered more for that than anything else now. Because there are people... Some things go beyond tennis. Some things go beyond sport. There are people out there that don't really care about tennis, may not even be that bothered about sport, that would have watched that. I think I mean listen I think that's why I would go Borg the Borg McEnroe Borg McEnroe Molden tie break right yeah for sure I do get that and listen I'm I'm going with something that had such a profound effect on me I'm being very selfish I know that Hannah's contribution in the chat is I feel like Jimmy Connors is mainly remembered for being a dick well that I also will concur with

52:29Borg left career on the table in a way that Connors didn't right I mean that 1991 run David was Connors rinsing everything out of his career Borg stepped away at the age of 26 and had he not made that comeback that he did in the early 90s I might not factor But the fact that he made that comeback suggests to me that he wasn't quite, didn't quite end up at peace with how much of his career he left on the table, as much as that was the only decision, the decision that felt right to him at the time. I mean, I know he's written a book and the answers to this question are probably in the book, but I've got a pile of, enormous pile of books by my bed and Bjorn Borg's autobiography is, it's on the list.

53:23but yeah it just I don't know who sent us have you started yet somebody has my address the publishers how do they have my address they met us at the US Open and they said would you like the book and I handed out my personal home address great here we are talking about it available to anybody that asks for it apparently look I do I do think the thing is had Borg done what Barty's done walked away happy knowing that this is what he wanted. How cool would that have been to be 26, walk away, 11 grand Sam titles, that'll do, you know. And he did walk away, but he walked away into a life of recklessness and sadness in many ways, I think.

54:15and that comeback was really sad. That was a miserable thing. He was burnt out. So it doesn't make me happy to think about the end of his career. Okay, I'm going for Connors. I don't want a miserable comeback, Matt. But it's funny because nobody really remembers that. They just remember 91 and they remember the tiebreaker and the underwear. You don't think of the sad comeback. Yeah, before David said that was a miserable thing, I really was leaning Borg. I think I will still go Borg. I think I would not want to pass up the opportunity to just look that cool on a tennis court and dominate Roland Garros.

55:11No, no, hang on, hang on. You'd still be you. Well, yeah, but do I look like Borg? I'm afraid, Matt, you look like you. So, OK, well, that does change things. Which is also great. Because I can be me. Yeah, yeah. Sorry, I should have made clear from the outset. We've been talking about the way people want. Personal appearance doesn't... Yeah, I... Yeah. I haven't been talking about that. But, yeah, I mean, that's fine. You can play like Federer, but you still look like you. That's fine. I just want to look like Borg. Well, you can't. That's not on the table. That's a different show. Well, then I guess we have to go Connors.

56:03I was trying to think of a one to end on. I was trying to think of one involving Thomas Johansson and a sort of a counter to him because, look, there's lots of single slam winners out there. I came up with Anastasia Moschina or Elena Dementieva. Of course, Moschina winning their French Open final and getting that Grand Slam title. Dementieva never got one, but she did get the Olympic gold and had an incredibly consistent career. And maybe that is an interesting one to debate. But I also, there's something about Thomas Johansson, David, and the fact that his name is a byword for kind of a fluke Grand Slam, isn't it?

56:53It is. Like, is, are you okay with having the slam if you're also sort of a bit of a punchline? I mean obviously he is okay with having the slam I think he's fine but do you know what I mean Thomas Johansson or Keina Shikori say Oh yeah Johansson I mean listen the value of a slam you can just never take it away and I always think back to Tim Henneman's face we hadn't even finished the question when we asked him would you rather have your career or Marin Cilic's and yet he'd reached all these Grand Sam semis and he'd been four in the world and he'd been Britain's top player and all these other things.

57:43Oh, he'd have his career in a heartbeat, he said, because he won a major. And that's before Cilic went on to reach other finals. It's just the one. And I'm sure Herman would say the same about Johansson. What about Moschino or Dementieva? I want to know your answer. Moschino. Because mine's Moschina. I think mine's Moschina as well. I thought it was going to be Dementiava. I think she was consistent, but I just can't not think of the double faults. Oh, God, I just wanted the ground to swallow me up. Unfortunately, the double faults are the first thing I think of when I think of Dementiava. I think Moschina was cool too.

58:31So, you know, she just went and won the thing and, you know, she wanted to play longer. We did that nice interview with her. Yeah. But I do think she's really cool. I don't know whether that factors in. Take the players out of it. I'm trying to think of players who would perfectly align for this, but one major versus one Olympic gold. What would be your choice? Or one major versus world number one, you know, a Jankovic. Oh, definitely the major. I would go with the major. The major I would go, I think, probably against the Olympic gold. There are a couple of players that I think the Olympic gold they would have chosen.

59:13Like, Nicolas Massoud, I think, would have chosen Olympic gold over the major. See, I think I would probably go for Massoud over Johansson, but I wouldn't go for... Would you go Massoud over Meskina?

59:29No. I wouldn't. And I can't explain that. And I wouldn't go for, oh my gosh, I'm blanking on her name. Puerto Rican. Monica Puig. One Olympic gold. Monica Puig. That's how much I've thought about Monica Puig recently. I wouldn't go for Monica Puig over Anastasia Moschina. But I would go for Nicolas Massou. And I can't explain that. but this is subjective and that's what I'm saying because there's something about with Puig and Johansson they achieved this one incredible peak but because of how the rest of their careers looked what else did Nicholas Massoud win he had a great Olympic singles and doubles coach Dominic Thiem oh here we go we're going to bring the coaching career in no I'm panicking now I'm panicking because I can't defend my Nicholas Massoud position it's indefensible I can't I can't it doesn't stack up on paper but there's just something about

1:00:53it feeling like a fluke it somehow didn't feel like a fluke for Massoud in the same way that it maybe did for the others. I can't defend it. Would he have been in the mix if we'd have been doing the show beforehand? Nicholas Massoud. No, none of these players would. Would Mesquina have been in the mix for that French Open? That's a good question. I don't think so. No. No? Okay. No. I mean, I think I'm right in saying that Ayrnham was a bit ill going into it. Yeah. We did this relive, didn't we? I'm pretty sure that's right. Worst Grand Slam finals. And lost early in that one. But Muschina beat, what, Venus?

1:01:37Beat Capriati? She had a very legit run to the title. Yeah. Oh, I've really enjoyed this. We didn't even get on to Bertic van der Zanschelp. That's why we have to have a second instalment. the question the couplet was van der Zanskiel or Tatiana Maria and the answer of course is Tatiana Maria isn't it I mean yeah I actually hadn't the Queen's moment I actually hadn't realised that until doing the research that Bottick hasn't won a title no I mean Bottick really hasn't hasn't done much at all and he's miserable throughout all of it I thought he would have won like I don't know Mets or something it's always Mets Or a Matty.

1:02:23There's still time. It's Tatiana Maria. Easy. It's Tatiana Maria, isn't it? But Burtick, he's got funny on his side. He does have funny. But the thing is, I'm not sure he finds it funny. Ininvertently funny. I mean, Tatiana Maria at Queen's was funny. She is funny. With all these big hitters just getting chopped up. Yeah. Yeah. Yeah, that's like, I'm afraid, Bertrand van der Zandt-Skrupp is the Richard Gasquet of this photo montage. He's got absolutely no right to be there. Folks, this has been really fun. I feel like there's loads more of these that we could do. And as players retire, there'll be, you know, the potential lists will refresh, which is great.

1:03:18Yeah, this has been really, really fun. And the chat has been really fun as well, particularly Hannah's contributions about Keina Shikori's sex scandal and Jimmy Connor's personality in general. I've really enjoyed those. And everybody's opinions. You know that a topic like this is going to divide the crowd and rile people up. But it's been fun. I've really enjoyed it. and we've almost finished in time for Celebrity Traitors. David, this is your chance to get into it. Yeah, I might go and give it a go. Yeah, go on, David. Folks, friends, thank you ever so much for being friends of the Tennis Podcast, for listening to this show, for joining us live.

1:04:03If you did tonight on YouTube, we'll be back very soon indeed. Our next show is coming on Monday. Who'd have thought it? A Monday show. We can't wait. Enjoy the weekend of tennis in the remains of Daniel Medvedev against Alex de Menor. It's been a fun evening. We'll speak to you very soon.

From the publisher

For our October live show, we discussed whose career we would rather have out of various Barge-nominated couplets. Federer or Nadal? Barty or Sharapova? Serena or Djokovic? Navratilova or Graf? Roddick or Medvedev? Henin or Clijsters? And many more! This was a fun one as we learned lots about what we value in a career.

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