In short
Steve Young discusses his early-career contract drama, the “40 million” USFL hype, and why he refused to cash San Francisco 49ers checks during a period he wasn’t playing, leading to tax/audit pressure.
Guest backgrounds
The episode is a clip featuring Steve Young (former NFL quarterback). No other guests are named in the transcript.
Key claims
Young says his USFL $40 million deal was promoted via annuity math; his mother corrected the “40 million down the drain” chant by noting it was an annuity. He recounts negotiating with 49ers/USFL owner Bill Oldenburg, where Oldenburg threw cash and security escorted them out. He claims he had “PTSD” from the $40 million episode and kept 49ers checks in a drawer until GM Carmen Policy called about taxes.
Notable examples
the stadium chant “40 million down the drain,” Oldenburg throwing a wad of hundreds, and Young’s checks left in a teammate’s dresser.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOSteve Young's Stunning $40 Million Deal
0:03 to 0:31
Steve shares his experience signing a groundbreaking $40 million deal and the ensuing chaos.
“So you were scrolling on Marketplace and there it was, the bike you'd been searching for.”
Steve Young's Stunning $40 Million Deal
0:44 to 3:30
Steve shares his experience signing a groundbreaking $40 million deal and the ensuing chaos.
“Between the guaranteed money and the annuity, it was supposed to pay out until you were what age?”
Handling Checks and Personal Growth
3:30 to 6:58
Steve discusses his unusual approach to not cashing checks during a tough time in his career.
“And he tries to say, you want to calm down?”
Transcript
Automatic transcript. May contain errors.0:00This episode is brought to you by Facebook. So you were scrolling on Marketplace and there it was, the bike you'd been searching for. You sent a message and it turned out the seller was super chatty, kind of funny, and an avid cyclist. The next thing you know, you're in a cycling crew. Well, a community cycling group. The thing about Facebook, you might find more than what you're looking for. From a browse to a bike ride, this summer, find more on Facebook. Hey guys, Graham here. It's Friday, which means we get to share with you another one of our most popular clips from a past interview. This week, Steve Young.
0:41The clip you're about to hear is trending on our Instagram right now. Hope you enjoy.
0:48The Express. It's the early 80s. You sign a$40 million deal. Between the guaranteed money and the annuity, it was supposed to pay out until you were what age? I think 60. And so, and they added up all the annuity payments for all those years and then called it$40 million. At the time, Wayne Gretzky was making$2 million and Magic Johnson was making$2 million. And then I was making$40 million. That's how it was promoted. It was worldwide. Every town I went into to play in the USFL, there was a sign, 40 million, you suck, you know, you're terrible. And it was a great story of my mom. They drove down from Connecticut to Washington, D.C.
1:27to see the USFL game. And I did something on the field, fumbled or something, and a chant started in the corner of the stadium where she was, 40 million down the drain. And the chant started to take the whole stadium, 40 million down the drain. And my dad tells this story, my mom's like, she stands up and everyone around her, you know, the guys and everything. And she goes, but it's an annuity. It's not 40 million. It's just an annuity. That's why he sucks. No, she didn't say that part. But it's just so funny that that my life again, how fast can we spend Steve? Let's give him let's say it's 40 million dollars and have him try to answer for that in a world where I didn't really want to answer for a dollar.
2:08Take me into the room where it's you and your agent Lee Steinberg actually negotiating that deal with a white. Oldenburg was the owner. Yeah. So he Goldenberg was a real estate developer. He takes me down to the Transamerica building where Lee and I were going to negotiate the final parts of the contract. Thought it was done. And so we go upstairs and we're getting done. And my dad is a lawyer, so he wants to be part of it. And he says, hey, I haven't read it. And Lee says, look, I don't know if we have time to read it. You know, he's got a birthday party and there's a big hoopla here. And he's like, look, I'm not signing.
2:45I'm not having my son sign unless I read it. So then Lee has to tell Mr. Oldenburg, we're going to have a little delay here. So the delay goes on an hour, hour and a half, and we're sitting in the conference room, just sitting there. And Bill Ormer comes in, and he was pissed. And he's like, he takes a wad of hundreds, like as big as you can hold. And he goes, you want more money? Is that what this is all about? You want more money? And throws it at me, hits me in the chest with the money, like flying money. And I remember thinking, I've never seen so much money in my life, you know? And I'm like trying to pick it up.
3:17And he storms out and has us escorted out of the building with security without the contract being done. Because my dad wanted to make sure that he read it. And yeah, that was the richest I ever was right there. And you almost took a swing at him. Oh, that's right. So I'm Mr. Oldenburg. You got to calm down. And he tries to say, you want to calm down? And he tries to, I'm like, hey, you need to, because he wasn't the biggest, you know, he's not a large man. And I said, you need to calm down because this is not going to go well. You know, that's how bad it got. Whether with the Express or the early in your 49ers days, you had an interesting way of handling your checks.
4:01Well, I think it's PTSD from the$40 million thing. So tell about the call you got from the then 49ers owner. It's nearing the end of the year and he's trying to close out his books. This is again a larger story. I'm in Tampa Bay. I'm, I'm, was the number one draft pick in the supplemental draft for the Bucs. And we would go two and 14, we're the number one draft choice. And the new coach Ray Perkins tells me, I don't like lefties, I don't like scramblers. Look, I was an oddity back then. Today's game I would be really cool, but back then I was odd. And I'd made a relationship with Q Culverhouse, the owner.
4:39And they traded me to the San Luis Cardinals. And he called and Ray Perkins says, hey, you've been traded. I'm like, oh no, that's the other team that's went two and 14. It's terrible. I called the owner and said, Mr. Colberos, we had a relationship. You said I was your quarterback for life and now I'm getting traded. He goes, I'm so sorry. Yeah, you're right. I'll mix that trade and you have a week to go figure out what you want to do. And Bill Walsh was the first call. And Bill said two things that just shocked me that I'd never heard in my whole life. I love lefties, which I'd never heard before.
5:07And I love people that can run around because I think there's a great benefit to it. And then he told me that Joe Montana had two back surgeries and, you know, I don't know when he's going to play again. So I come to the 49ers and I have the sense that maybe I'm going to play. And the first practice, Joe Montana runs out and he's, he looks great. And I turn to Bill Walsh and I go, he's not hurt. And Bill's like, you know, sorry about that. So that That started a six year odyssey for both of us, for the three of us, that was pretty dramatic. And I think part of that drama was when I wasn't playing, the one thing I didn't want to do was sit around.
5:54I'd rather go to law school than sit and watch. This is the immaturity and stupidity of me. I was like, I'm not going to cash my check. You know what, I'm just going to let him sit in the drawer because I'm not playing, so it doesn't matter. And I was renting a little room from Harris Barton, my teammate. And I went back to law school in the offseason, and Carmen Policy called me and said, general manager of the team, and said, hey, look, you're screwing up the taxes. Where's the checks, man? You know, we've got to file. It's April. We've got to file. And I forgot I'd left him in the drawer in Harris' house, so I called Harris.
6:29I go, Harris, would you go into my room and just see if they're all in there? and Harris, he tells a funny story, he goes in there and he's like 16 checks, you know, pretty big checks. He's like, what are you doing man? And I go, do me a favor. You remember for how much? You know, it was good money. Four million dollars you just said sitting in your dresser door. So I said, do me a favor man, you know, would you gather them and send them to me? Because I got it, I got it. Back then there was no, you know, you couldn't take a picture of it or anything. And so he sent them to me. We got them. I finally gave in because of the audit for the 49ers.
7:05Reluctantly gave in Graham. Reluctantly. Before you leave, here's a quick shameless plug. Please follow us at Graham Bensinger on Facebook, YouTube, Instagram, TikTok, and Snapchat for tons of new content each week.
From the publisher
Football legend Steve Young looks back on his time in the USFL and on the 49ers. He details his $40 million deal with the USFL’s LA Express and joining the San Francisco 49ers as a backup quarterback to Joe Montana. He also remembers the “interesting” way he handled his checks in his early 49ers days.




