Trump’s New Middle East Dilemma, and How DraftKings Uses A.I. to Target Gamblers

21 Sep 2026 · 11 min · 4 chapters

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In short

This episode of The New York Times’ “The Headlines” covers three main stories. First, Trump’s Middle East dilemma: U.S. officials say Trump nearly launched airstrikes against Yemen’s Houthi militia, with commanders approving target lists, but he paused. The debate includes Saudi Crown Prince pressure to act versus skepticism inside Trump’s inner circle due to strain from the Iran war. The Houthis have rebuilt capabilities after earlier U.S. bombing, used AI to engineer new missiles, attacked Riyadh with drones/missiles, and seized Yemen’s Red Sea coastline. Second, DraftKings: former employees and internal documents suggest the company uses machine learning/AI to target gamblers with personalized promotions, raising concerns about “predatory technology” amid rising addiction calls (Ohio hotline up 4x since 2023). DraftKings denies improper targeting, saying it focuses on “betting within their means.” Third, other headlines: White House bars CNN/Politico/MSNBC journalists; drafts an NIH funding veto committee; and deportees to Equatorial Guinea faced alleged abuse.

Guests

no specific guests are interviewed; the episode features NYT reporters (e.g., Haley Bailey, Tracy Mumford, and data journalist Alex Clavins).

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

Chapters

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Trump's Airstrike Dilemma

0:28 to 2:15

Discussion on Trump's indecision regarding airstrikes against the Houthi militia.

“The Times has learned that over the weekend, President Trump was on the verge of launching new airstrikes against the Houthi militia in Yemen.”

Press Freedom and White House Actions

2:33 to 4:22

Overview of recent restrictions on journalists and the implications for press freedom.

“Now, three more quick updates on the administration.”

Violence Against Deportees in Equatorial Guinea

4:42 to 5:43

Examining the conditions faced by deportees in Equatorial Guinea and human rights concerns.

“Equatorial Guinea is one of the places the administration struck a so-called third-country deportation deal with to accept deportees who have no connection there.”

Top TV Shows of the Century

9:15 to 11:06

Discussion on the list of best TV shows of the 21st century and its creation process.

“Elena Ferrante's My Brilliant Friend took the top spot.”
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Transcript

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0:00If you like YouTube, you'll love YouTube Premium. Hi, I'm Haley Bailey. With YouTube Premium, I get ad-free videos, offline downloads, background play, and so much more. So try YouTube Premium for two months free at youtube.com slash premium. Trial eligibility varies. Terms apply. Cancel anytime. From The New York Times, it's the headlines. I'm Tracy Mumford. Today is Monday, September 21st. Here's what we're covering.

0:28The Times has learned that over the weekend, President Trump was on the verge of launching new airstrikes against the Houthi militia in Yemen. According to Trump administration officials, yesterday morning, U.S. troops were loading bombs onto warplanes and commanders had approved lists of Houthi targets before Trump decided not to move forward, at least for now. The officials say that for the past two weeks, Trump has been going back and forth about whether to strike the Houthis, who are allied with Iran and have recently reignited fighting with Saudi Arabia. On one side, Trump has been hearing directly from the Saudi crown prince, a major U.S.

1:08ally, who has called the president directly to implore him to step into the fight. At the same time, one senior administration official said that most of the president's inner circle has been either deeply skeptical about joining the fight against the Houthis or have opposed it outright, especially given existing strains on the U.S. military caused by the ongoing war with Iran. There are also major questions about how effective any new U.S. strikes would be. Last year, Trump ordered nearly eight weeks of bombing against the Houthis, with U.S. forces hitting more than a thousand targets like radar systems, ballistic missile sites, and a drone production hub.

1:49But since then, the militia has rebuilt much of its capabilities and has even been using AI tools to develop and engineer new types of missiles. This weekend, the group said it launched a wave of drones and missiles at Riyadh, the Saudi capital. And recently, the Houthis have taken control of Yemen's entire Red Sea coastline, which could further disrupt another crucial shipping route in the Middle East for oil and gas. Until now, the group hasn't been attacking U.S. ships in the region. But one administration official said that if Trump does order strikes against the militia, that would probably change.

2:33Now, three more quick updates on the administration. First. So I walk in, I tap my badge, and it beeps a couple of different times. It turns red, blue. Journalists from three news outlets, CNN, Politico, and MS Now, have been barred from entering the White House. So the officer asked me to hand over my badge. He said that it was disabled. President Trump announced the ban on Friday, saying it was punishment for publishing, quote, purposely negative stories that he said were untrue. Many other mainstream media outlets, including journalists at Fox News, condemned the move, and legal experts say the ban is a clear First Amendment violation that's unlikely to survive a court challenge.

3:18It is a major escalation of Trump's ongoing battle with the press that covers him. This summer, FBI agents served subpoenas to reporters at their homes, And the Pentagon has blocked access to journalists who refused to sign pledges that would limit their reporting. Also, the Times has learned that the White House is taking a new step in its pressure campaign against universities. It's drafting an executive order that would cement the president's ability to control who gets billions of dollars in federal research money from the National Institutes of Health. Traditionally, the NIH has selected projects based on expert review of their scientific merit, funding labs across the country, many at universities, for research into things like heart disease, cancer, infectious diseases.

4:09But the executive order would create a new external committee with the power to veto any grants that don't conform to the president's political agenda, according to people with knowledge of the draft. It appears to be the latest attempt by the White House to cut off funding to universities it's accused of promoting woke ideology. In response to questions from The Times, a spokesman for the NIH said the agency remains committed to funding research, quote, to benefit the health of the American people. And The Times has learned that people deported by the Trump administration to Equatorial Guinea have been facing violence and abuse.

4:51Equatorial Guinea is one of the places the administration struck a so-called third-country deportation deal with to accept deportees who have no connection there. After arriving in Central Africa from the U.S., one man described the Times how they'd been held indefinitely in a run-down hotel that became a de facto prison, texting, We are in imminent danger now and can't keep living like this. Then, after speaking out about the conditions there, he and another man were tied up, beaten, and shoved down a flight of stairs by police officers, according to witnesses and lawyers. Experts and human rights advocates had warned about this kind of violence when the White House started striking these deals with authoritarian countries.

5:35The State Department itself previously said that Equatorial Guinea is notorious for human rights violations, including torture. The government of Equatorial Guinea didn't respond to requests for comment. In a statement, the Department of Homeland Security said Equatorial Guinea was, quote, safe.

5:59Boom! DraftKings casinos combining two things I love, touchdowns and bonus rounds. Over the last decade, the online gambling company DraftKings has become a big brand in American life. popping up with online ads, billboards, etc. Spin your way at DraftKings Casino and experience FlexSpins. It started out focused on sports betting and has now moved into online casinos and prediction markets. DraftKings has basically helped make gambling accessible to millions of people right on their phones. And with phones comes user data. A lot of user data. I was curious, what are these companies doing with your data?

6:43So I started reaching out to former employees of DraftKings. That included data analysts, software engineers, people who were in the room actually building the technology. And what we found was a lot of them had serious regrets about their work and about how customer data practices were targeting certain types of gamblers. My colleague Alex Clavins is a data journalist. He's part of the team behind a new investigation about how DraftKings has harnessed users' information. They talked with dozens of former DraftKings employees and reviewed internal company documents. And Alex says a big thing that jumped out is how DraftKings has tried to hone its promotional offers, things like an email offering a free bet, to keep people playing.

7:34One analyst I spoke with said that he was part of one of the earliest efforts to use customer data and to use machine learning, which is a type of artificial intelligence used to find patterns in data and predict outcomes to figure out who would be the best targets for the company to send promotions. And he grew concerned that people that the algorithms would identify as good targets could have gambling problems. He was not the only one who raised those concerns. Several people who my colleagues and I spoke with who worked directly on these systems grew worried that they were building what they described as predatory technology.

8:17Alex says all of this is happening as concerns about gambling addiction are growing across the country. For example, calls to one gambling hotline in the state of Ohio have more than quadrupled since sports betting was legalized there in 2023. One DraftKings user who sought treatment for gambling addiction told The Times that just opening up his email inbox felt like a relapse risk. Records show that over the course of just two weeks, he got 40 promotional offers from DraftKings. In a statement, DraftKings said it rejects any implication that its marketing practices improperly target customers.

8:57And an executive said the company is focused on people who are, quote, betting within their means, are betting for entertainment and betting for fun. You can read the full investigation at NYTimes.com.

9:15And finally, my colleagues inspired a lot of strong feelings when they rolled out the list of best books of the 21st century. Elena Ferrante's My Brilliant Friend took the top spot. There were even more feelings when they put out the list of the best movies of the century. Parasite took number one. Now they're doing best TV shows, so get your hot takes ready. To pull together this ranking, my colleagues reached out to hundreds of actors, showrunners, and others in the industry to get their opinions. And the list is coming out starting today, counting down from number 100 to 81. The list includes interviews with some of the stars of the shows.

9:59I started working on Gilmore Girls when I was 18, so I'm very grateful for it. You really like my table, don't you? Like Alexis Bledel of Gilmore Girls, which squeaked in at 99 on the list. Also, When something looks like a movie and takes you on a journey that you've never been to before, it's a show to watch. There are industry names talking through their ballots, like Giancarlo Esposito of Breaking Bad and Better Call Saul talking up his pick, Shogun, the drama set in 1600s feudal Japan that came in at 86 on the list. There's a dash of reality in there, too. The Great British Baking Show is in this batch today at number 85, since Bake Off has taught us all a lot about total failure and what technically makes something an eclair.

10:46The first part of the list is up now on the Time site. More rankings will drop every day this week with the top 20 TV shows of the century coming Friday. And before anyone asks why The Sopranos is not on there, it debuted in 1999.

11:05Those are the headlines. Before we go, we want to hear from you with your questions about AI. Can AI hack my bank account? What does recursive self-improvement even mean? And why does everyone keep talking about doomsday? Any question is fair game, and we'll have some answers from Times reporters who are covering the technology. So if you have an AI question, email us at theheadlines at nytimes.com. I'm Tracy Mumford. We'll be back tomorrow.

11:41This podcast is supported by Charles Schwab. Decisions made in Washington can affect your portfolio every day. But what policy changes should investors be watching? Washington Wise is an original podcast from Charles Schwab that unpacks the stories making news in Washington right now and how they may affect your finances and portfolio. Listen at schwab.com slash Washington Wise.

From the publisher

Plus, the best TV shows of the century. 

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Trump’s New Middle East Dilemma, and How DraftKings Uses A.I. to Target GamblersThe Headlines · 11 min
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