William Cohan, the author and Puck journalist who spent close to 20 years as a Wall Street banker before turning to journalism, talks to Kara Swisher about his new book on Leon Black, the Apollo co-founder whose ties to Jeffrey Epstein forced him out of the firm he built. They go through the Drexel origins of Apollo, the $158 million Black paid Epstein and the explanation Cohan says he cannot disprove, the private credit machine Mark Rowan built on top of an annuity company, and then the rest of Cohan's beat: the AI bubble, Meta's settlement, tariffs and the bond market.
👤 Guest: William Cohan, author and Puck journalist, a Wall Street banker for close to 20 years before he switched to journalism, whose new book Money to Burn is about Leon Black and Apollo
🎙️ Host: Kara Swisher, host of On with Kara Swisher from New York Magazine and the Vox Media Podcast Network
👥 Also on: Bethany McLean, a contributing editor at Vanity Fair and an author of The Smartest Guys in the Room, who recorded the episode's expert question
📰 Published: 31 August 2026
🟢 Spotify | 🟣 Apple Podcasts | ⏱️ 57 min | ✅ Time saved: TIMESAVED min
Key Takeaways
Apollo was built to buy a company's debt at a distressed price and end up owning the company
"No one else was doing that when Apollo was founded in 1990."
Vail is the example: Black advised the owner, financed him with Drexel junk bonds, bought the bonds back at a discount when they fell, converted them and kept the resort
The founders knew which bonds were distressed because they had underwritten them
"And of course, they all came out of Drexel Burnham, which means they were all part of the Mike Milken junk bond machines."
Black went into finance because his family needed the money, not because he wanted the job
A philosophy major at Dartmouth whose thesis had nothing to do with business, he turned down Goldman Sachs and went to Drexel after his father's death and the collapse of United Brands stock
Apollo's second act is private credit, and it funds itself with retirement annuities instead of deposits
"They have about a trillion dollars of assets under management now, 850 billion of which are private credit."
The risk in that model sits with the annuity holder, not the borrower
"Like their promise, say, 5% a year on their money for seven or 10 years. And Apollo was taking that money and investing it, lending it out at 10 or 11% and then probably using some leverage on top of that."
Cohan asked Black to his face how a man that sophisticated made himself vulnerable to Epstein
Black's answers were that life is complicated, that he was not the only one, and that plenty of rich men pay for silence
Apollo's own review cleared Black and put the payments at $158 million, and a senator disputes even that
"By the way, he says it's 170, not 158. I'm not sure where he gets that number, but he's sticking with it."
Black gave three reasons for staying with Epstein after the guilty plea, and Cohan reports them without adopting them
An ID card, a served sentence and a belief in second chances — "He gave Martha Stewart a second chance. He gave Al Taubman a second chance. He gave Sam Waksal a second chance, all, either convicted or pled guilty to crimes."
Cohan wrote in Vanity Fair that the story was not credible and says he still has nothing to disprove it
"You know, one of the two main parties to this whole matter is dead."
The AI infrastructure will outlast the people paying for it
"I mean, AI is not going away. Just like the Internet wasn't going away, we needed the infrastructure"
A correction starts with a loss of confidence, and nobody sees the trigger coming
"But what always is the same, Kara, is that it triggers a loss of confidence."
Meta's $17 billion settlement looks cheap against what a jury might have done
"And it could have been hundreds of billions of dollars. 17 billion sounds cheap to me."
The bond market is the warning, and the interest bill is already bigger than the military one
"We spend more than a trillion dollars a year now on interest expense."
A run is a run, however good the assets behind it
Silicon Valley Bank held Treasuries and was liquidated anyway — "It doesn't really matter sometimes how good your assets are."
Apollo Was Built to Buy the Debt and End Up Owning the Company
Swisher opened by asking why anyone should care about Leon Black when private equity billionaires are, as Cohan put it, a dime a dozen. Cohan's answer was that the firm was built differently from the start.
He rates the industry itself before he rates the man. "I don't think there's a better business you could have been in that is both legal and, and can make you as much money as private equity did for the last 40 years."
"It's kind of hit on more difficult times these days."
The ordinary leveraged buyout takes the equity. Apollo went after the rest of the capital structure. If bonds were trading at a distressed level Apollo could buy them, and if the company defaulted or went into bankruptcy it could convert those bonds into equity and take control that way
"And they did that, repeatedly. No one else was doing that when Apollo was founded in 1990."
The edge was information, and it came from Drexel. "And of course, they all came out of Drexel Burnham, which means they were all part of the Mike Milken junk bond machines." They knew where the distressed bonds were because they had underwritten them in the first place
Vail is the worked example. Black advised George Gillett on buying Vail and other assets using Milken's junk bonds; the company ran into trouble and the bonds traded down
"Leon bought the bonds at a discount, converted it to equity, and ended up with Vail Resorts, and made a fortune."
What set Black apart personally, Cohan said, was that he did not want to be like the rest of Wall Street — he went to Drexel rather than a traditional bank, ran mergers and acquisitions there, and when Drexel imploded built a firm with the flexibility to buy any security he wanted
Swisher's reply — "So innovative flimflammer is what you're saying to me. I'm teasing." — got a careful answer: "Certainly innovative. And, obviously it's all legal." Black made the deals and then took advantage of them, Cohan said, and got a lot of criticism for it
The Escape Artist: Drexel Fell, Executive Life Fell, and Black Walked Away Richer
"You know, the amazing thing is he was like incredible escape artist too because Drexel went down and he didn't get in trouble."
In the Executive Life affair he bought $6 billion of First Executive junk bonds at 50 cents on the dollar, watched most of them trade up, converted a lot of them to equity and bought the companies
The run ended with one relationship. "But he was an escape artist until he got caught up with Epstein, and he got stuck with the Epstein paper."
A Bribe Over Bananas, and Why a Philosophy Major Went Into Finance
Swisher set up the family history: Black was getting his MBA at Harvard while his father, Eli, ran United Brands, the conglomerate then coming apart, and Eli Black died by suicide.
He had not wanted the MBA in the first place. "He was a philosophy major at Dartmouth, of all places." Cohan called the thesis interesting and intellectual, with nothing to do with business
The scandal was a tariff story. "It has to do with tariffs, Kara, believe it or not." United Brands was the largest importer of bananas from Latin and South America, and tariffs imposed by Central and South American countries were wrecking its income statement
The executives' answer was a bribe to the Honduran finance minister, which Cohan called small potatoes by today's standards and a big scandal at the time
The family's money was in United Brands stock, which fell on the news. Black's mother was an artist, his aunt an art dealer, his sister a teacher, and he became the breadwinner
"So that's why he went into finance. He needed to make money."
He turned down an offer from Goldman Sachs to go to Drexel instead, and Cohan said he had no aptitude for it as such
What Milken Built, and the One-Page Letter Black Invented to Sell It
Swisher raised Connie Bruck's book on Drexel and asked about the firm as the outsiders' house against the white-shoe banks. Cohan agreed: "Absolutely. They were the renegades."
The junk bond market is the innovation, whatever happened to its inventor. Milken pled guilty to securities violations after saying he would not, went to prison and has since been pardoned by Trump
"I mean, basically, we wouldn't have a cellular, telephone industry today without Mike Milken and his junk bonds or cable industry. And those are just two small examples."
"He understood that investors could make more money buying junk bonds than they could the bonds of investment grade companies. I won't bore your listeners with why."
"So he financed the companies that other people wouldn't finance." He also financed raiders, Carl Icahn among them, to buy companies they could not otherwise afford
Black's own contribution was the highly confident letter — a note from Drexel saying it was highly confident it could raise the money for a bid
"And it was really just a puff of smoke and a cloud of dust." There was nothing behind it, Cohan said, but Milken's record at raising capital made it work
Why Black was good at the job: he was smart, insightful and savvy, and he was one of the Wall Street people who can turn it on in a client meeting whatever they are like with their own staff
"With clients, they can be mesmerizing. And Leon was one of those guys."
The scale of the money is what made the fall hurt. "Don't forget, Mike Milken was paid $550 million, $550 million for an investment banker in 1987 was unheard of." Black was head of mergers and acquisitions and getting fabulously rich; Milken pled guilty and left, and the firm had a run on the bank in early 1990 and was liquidated
The New Wall Street Is Private Credit, and It Runs on Annuities Rather Than Deposits
Swisher moved to Apollo itself, which Cohan calls the new Wall Street in his subtitle. He was clear that the phrase is about the last 18 years rather than the founding.
Mark Rowan, who became chief executive in 2021, is to private credit what Milken was to junk bonds, Cohan said, and that is the change the book is about
"And that's why the subtitle includes the idea of a new Wall Street."
It is bank lending without a bank. Apollo takes no deposits; its capital comes from Athene, the insurer it created, which sells annuities to people who want a fixed rate of return for a set number of years
"So their money is sort of long-term capital that they then use to provide long-term financing to all sorts of companies."
The scale: "They have about a trillion dollars of assets under management now, 850 billion of which are private credit." Black is out of the firm but remains its largest shareholder
"So he's created a juggernaut."
Everyone else copied it — Cohan named Blackstone, KKR, Brookfield and TPG as the alternative managers that followed Apollo into the business
The worry of the last nine months is whether the thing cracks. Retail investors in private credit funds asked for their money back and discovered they could take out only 5% of it, and made a lot of noise about it
"But I think the people like Mark Rowan, who are the mad scientists behind private credit, are basically saying this is overblown, you guys are overreacting, and everybody just calmed down."
Who Actually Carries the Risk: the Person Holding the Annuity
Swisher pressed on whether any of this is good for ordinary people, and used her own framing for the lock-up: "You can check in, but you just can't check out." Cohan went through it party by party.
"Yeah, it's great for Apollo. Okay, we can stipulate that."
Probably good for the borrowers. The capital is not cheap but it is available and more flexible than bank capital, and there have not been many defaults
Probably well priced for the investors, on the evidence that Apollo takes about 20% of each deal it puts together and would not do that with paper it disliked
The risk sits at the other end. "Like their promise, say, 5% a year on their money for seven or 10 years. And Apollo was taking that money and investing it, lending it out at 10 or 11% and then probably using some leverage on top of that."
Cohan said the book explores whether what Apollo has really built is a different form of a bank. If it cannot pay the annuity holders their 5%, "The whole kit and caboodle is in big trouble."
"They can't go to the ATM machine like they could at Silicon Valley Bank, but they can get their money out." It may cost them a penalty, and the assets behind them are tied up for seven to ten years
Hubris, an NDA and $21 Million: How Cohan Put the Question to Black
Swisher listed what the money bought — the art collection, the seat on the board of trustees at MoMA, the homes, the yacht, the jet — and put to him that an unnamed Wall Street veteran had said Black's weakness was hubris. Cohan answered by describing how he framed the question to Black himself, over many hours of interviews.
The set-up was flattery, and then the question. "There was a cover story in Business Week, with one word title calling you ruthless."
"How could you do something so stupid, Leon, to get involved with Jeffrey Epstein or to have an affair outside of your marriage that you agree to pay this woman $21 million and signed an NDA and then she blows it up?"
The first answer was that "life is complicated", delivered alongside the observation that he is also the man who bought Old Master drawings at eight figures apiece — "I'm also the guy who spent $50 million each for two small Raphael drawings"
The second answer was that he was not alone. As Black pointed out to him, Cohan said, there are hundreds of rich men within a one-mile radius of where the two of them were sitting who have had affairs and had the women sign NDAs, and he would know many of them
"And this is sort of par for the course."
Swisher did not take it: "Well, that's no excuse." And then again, "Again, not a great excuse."
$158 Million, a Handwritten List and the Report Apollo Commissioned
Swisher's framing was that Black denies any knowledge of Epstein's crimes but stayed involved with him for years after the 2008 guilty plea, and that "His name comes up more than 8,000 times in the Epstein file, so that's kind of a dumb excuse." She asked how Epstein got access to people like Black, Bill Gates and Bill Clinton.
Black had the list on him. "You know, when I first brought up Epstein, we were having lunch in his office, and he went over to his jacket pocket and pulled out a handwritten list of all the people who were involved with Epstein"
Asked what Epstein was actually doing for all of them, Cohan said: "That remains one of the biggest mysteries, right?"
Black asked Apollo's board for the outside review that became the Dechert report, a deep dive into the relationship, and told Cohan he asked for it because he knew he had done nothing wrong
"The Dechert report did not find any wrongdoing. They found that he paid him $158 million."
The Tax Structure a Room Full of Lawyers Could Not Fix
Swisher read Black's position back to him — that the money was for legitimate business dealings related to tax and estate advice, and that he told Cohan "I've never been that sophisticated tax-wise" and had never added up what he had paid.
Cohan's account of the mechanics starts with a failure by the professionals. Black had a tax and estate planning problem created by a very sophisticated lawyer who was supposed to be an expert in it
"He went to Epstein. Epstein looks at the documents. He was no tax and estate expert"
The fix turned on giving money back. Epstein's solution had the whole document set redrafted to remove the potential liability, with Black in effect handing back $400 million he was not entitled to, which supplied the consideration the redraft needed
It has held. "And, it has never been challenged by the IRS." Cohan noted that Ron Wyden talks about it constantly and thinks something must be wrong with it
"But Epstein's solution in just this case was very clever, very insightful, and then vetted by the Paul Weiss's, the Sullivan and Cromwells, etc." They all signed off on it, he said, and he has looked hard and been unable to find a flaw
Cohan's own conclusion on that narrow point: "So he had a good idea."
Black's Three Reasons for Staying After the Guilty Plea
Swisher asked how Black justified working with Epstein for roughly a decade after the plea: "Like, there's a lot of smart people that don't sleep with minors." Cohan laid out the justification as Black gave it to him, and did not adopt it.
One, an ID. "He said, one, that Epstein told him that the girl slash woman showed him an ID card that showed she was older than 18." Swisher: "Yeah, the old excuse." Cohan: "Of course, the old excuse."
Two, a sentence served. "Number two is he thought, okay, he paid his penalty, even though we now know it was incredibly lenient and kind of a joke."
The second chances Black offers as precedent: "He gave Martha Stewart a second chance. He gave Al Taubman a second chance. He gave Sam Waksal a second chance, all, either convicted or pled guilty to crimes."
"You know, he's given Mike Milken a second chance and a third chance and a fifth chance."
Three, that he did not know the rest of it. Black told him he did not know about criminal activity beyond the offence Epstein pled to
The work expanded well past the tax problem. "He then wormed his way into Elysium, his family office. He helped me buy boats and planes and artwork and sell them all in tax-efficient manners." There was no written contract for any of it
"And then when the Dechert people totaled it up and it added up to $158 million, that was apparently news to Leon because he had never added it up before. So he just was paying the bill."
Cohan Wrote That the Story Was Not Credible, and Still Cannot Disprove It
Swisher read back what Cohan wrote in Vanity Fair when the review landed — "nice try, Leon, you must think we're pretty stupid, gullible, or insane to believe the tale you spun to the investigating firm" — and asked what he would say now, after sitting with Black repeatedly for the book.
"I still think that people are incredulous about the amount of money he paid to Jeffrey Epstein and the reason for that." Black knows he read it, Cohan said, and knows he is skeptical
The reporting ran into a hard limit. "You know, one of the two main parties to this whole matter is dead."
He has been through a lot of the three million files, especially where Black is involved. "Epstein ranted against him in these crazy emails, Kara, and then Leon never responded to the emails."
"But, I don't have any evidence to refute what he is saying."
The other allegations. "Now, he obviously had women on the side, and he got in trouble with one of them, and maybe others."
"There's been other allegations made against him, not just Ganieva, but two other women as well. And the lawsuits have been thrown out, basically."
Swisher raised the wider set of names around Epstein, including Les Wexner; Cohan added Glenn Dubin and said there are plenty of people who have gone unexplored, while Black has been examined more than most
A digression on estate planning, which Cohan offered as part of why Black leaned on someone: it gets bizarre enough that you cannot follow what you have done as you walk out of the lawyer's office. Swisher was unmoved — "I'm pretty clear on what I've done, actually." — and got "Okay, well, you're smarter than the average bear."
Why the Relationship Ended, and Why Black Sat for the Book
The break came over money and email volume. Epstein was constantly harassing Black for more, late at night, in what Cohan called verbal diarrhea
The payments were not deductible after all. "So he thought he was paying with $0.60. He wasn't. He was paying with $100.00."
"So I think he just got pissed off at Epstein with his relentless desire for more and more money. And he said, that's it. You're out of here."
Black came to Cohan, not the other way round. "He reached out to me, Kara. I didn't even get a chance to call him up." He assumed Cohan would want to talk to him, and then gave his time endlessly and on the record
Swisher noted how unusual that is. "They don't like to be on the record. They'll tell you everything off the record."
What Cohan thinks Black wanted: "I think he would like a Milken-like redemption if you could get one. I don't think he's going to get one."
Milken, he noted, pled guilty to crimes he was later pardoned for, had prostate cancer and has been very helpful to the cancer drive
Why Epstein Stuck to Black Longer Than to Anyone Else
Swisher pointed out that Black resigned as chief executive and chairman of Apollo in March 2021 and yet has not exactly been canceled — he is still on the board of trustees at MoMA and still has ties to the Met — and asked what the real impact has been, given Gates, Clinton and Summers.
"Leon has stuck on him a lot longer than pretty much everyone else."
"The sum of money he paid him, as we discussed, is much higher than anybody else, large margin." There is also a public report, a senator and the volume of file references
Cohan's rule for surviving it is not to engage. "I mean, if Larry Summers had just not responded, he would not have been canceled." Swisher added the detail about asking Epstein for dating advice, and the two of them left it at "Keep it classy, Larry."
On why Milken gets an easier ride than Black in the press, Cohan said Black has kept most of the media at a distance, and that the coverage has been cruel because of what the mention of Epstein does to a name
Wyden Wants the Tax Story, Comer Wants the NDAs
Swisher set out the state of play: the Epstein files released by the Justice Department contained further allegations against Black, including multiple allegations of assault. "We're not going to share the details, but Black strongly denies the substance of all of them." Both the House Oversight Committee and the Senate Finance Committee are looking at him. She asked what the biggest unanswered question is.
Wyden's interest is the money and the tax argument around it. "Well, Wyden is just skeptical about the whole 158 and what it was for. By the way, he says it's 170, not 158. I'm not sure where he gets that number, but he's sticking with it."
"He's been sort of, quote, unquote, exploring how billionaires don't pay their fair share of taxes, and he thinks that Leon is Exhibit A."
Comer's interest is the non-disclosure agreements, on a theory that Epstein advised on them. "He's threatening now to hold Leon in contempt of Congress if Leon doesn't cough up these NDAs"
Cohan doubts there are many. The Ganieva agreement is public because of the litigation and Black has offered to share a second one
The structural problem with the demand: "And if Leon unilaterally gives it to Comer without permission from the other person who signed it, that's breaking that contract. So he can't do that."
"Comer is, I think, also wants to run for governor of Kentucky." Cohan reads the investigation as a possible political stepping stone
"So the two of them were really at loggerheads at the moment, literally in real time."
Where It Leaves Him: Largest Shareholder, $15 Billion, and a Name Nobody Wants On a Gift
"He told me he has more than a billion dollars in his philanthropy to give away, and he struggles to give it away because there's the Leon Black Taint."
"His art collection is astounding. Absolutely one of the most incredible I've ever seen."
"He's on GLP-1s, so he's lost weight. He looks better." Cohan described him striding the halls of Congress in Ray-Bans on his way to testify
"I mean, his son, Ben, is in the Trump administration. One of his other sons works at Apollo. I mean, you could be worse. He's worth $15 billion."
Why He Wrote It, and What Black Makes of It
Two reasons, and the first is the character. "I love writing these incredible stories about these incredible characters."
The second is the industry. What Rowan has done with Athene changed Wall Street, Cohan said, and how it plays out is not known yet
"And a lot of people are very worried that it's going to lead to the next financial crisis."
The Epstein files were a windfall he had not counted on. "I got lucky that this whole Epstein blew up, and there was three million files that I never even thought I'd have access to, many of which involved Leon." He had started the book before any of it
Black was getting his copy the day of the recording. Asked how Black comes off, Cohan said: "Fair and balanced. I hate those words because they're Fox News-laden, but he's had his say. He explains it all in detail."
"The other side of it is dead." Cohan expects his account to stand until the remaining files come out, which he thinks may never happen
Get the latest market chatter as it happens:
If this saved you the listen, send it to one person who would rather have the time back.