Legendary private equity deals

01

Leon Black

Leon Black paid Jeffrey Epstein $158 million in fees for 'tax advice,' then resigned as Apollo's CEO the day the math became public. The firm he built manages $500 billion. The advice cost more than most countries' GDP per capita.

02

Cerberus Capital Management

Cerberus Capital — named for the three-headed dog guarding the underworld — bought Chrysler from Daimler for $7.4 billion in 2007, then watched it go bankrupt in exactly 735 days. Hell kept the dog; taxpayers kept the bill.

03

RJR Nabisco

In 1989, KKR bought RJR Nabisco — cigarettes and Oreos under one roof — for $25 billion in a feeding frenzy that spawned a bestselling book and a defining Wall Street myth. Who actually won?

04

Michael Milken

Michael Milken financed the 1980s on junk bonds, paid a then-record $600 million fine, served 22 months in prison, and emerged rebranded as a cancer-research philanthropist. The decade he dismantled made him a saint.

05

Simmons Bedding Company

Simmons Bedding — maker of the Beautyrest mattress — was bought, loaded with debt, and sold seven times in a single generation of private equity deals, each time leaving workers with less and investors with more. The mattress never changed.

06

Toys "R" Us

KKR, Vornado, and Bain Capital bought Toys 'R' Us in 2005 for $6.6 billion, immediately saddled it with $5 billion in debt, and spent 13 years watching 33,000 employees lose jobs as the debt ate the stores.

07

Stephen A. Schwarzman

Steve Schwarzman spent $3 million on his 60th birthday party — a Rod Stewart performance, a portrait of himself unveiled mid-room — then wrote a memoir advising readers to 'never do anything small.' The portrait still hangs at Blackstone.

08

The Carlyle Group

Carlyle Group counted George H.W. Bush, John Major, and James Baker among its advisers or board members simultaneously — while investing billions in defense. On September 11, 2001, Carlyle's investor conference was meeting in Washington, D.C.

09

Apollo Global Management

Leon Black founded Apollo after being effectively pushed out of Drexel Burnham Lambert in 1990. The SEC barred him from the securities industry — then watched the firm he built grow to manage $600 billion. Bars, it turns out, are negotiable.

10

Drexel Burnham Lambert

Drexel Burnham Lambert collapsed in February 1990, wiping out in days the firm that had financed the entire decade of hostile takeovers. It left a $650 million crater and 5,000 unemployed bankers before a single competitor blinked.