Once one of the city's more prominent financiers—and a former city official, screenwriter, and celebrity pal—Lipper's hedge fund crumbled amid scandal in 2002. These days he's an executive vice president at real estate giant Cushman & Wakefield.
The son of a shoe salesman, Lipper grew up in the South Bronx and attended Columbia and Harvard Law before tacking on another degree at NYU. He only spent a couple of years practicing law at the firm Fried, Frank: When he married Evelyn Gruss, the daughter of Texas oil and gas magnate Joseph Gruss, he was granted entrée to the world of high finance and joined Lehman Brothers, climbing the ranks quickly to become one of the firm's youngest partners. John Gutfreund lured Lipper to Salomon Bros several years later; following the firm's public offering in 1982, Lipper cashed out and turned his eye to city politics.
In 1983, he joined the Koch administration as deputy mayor and served as one of the mayor's chief negotiators, doing battle with city bureaucrats and longtime Koch foes like real estate developer David Walentas. After Lipper's own political ambitions failed to pan out—he lost a race for City Council in 1985—he entered the glamorous world of filmmaking when director Oliver Stone asked him to advise on the making of Wall Street. Lipper helped hone the dialogue and coached Michael Douglas and Charlie Sheen (and even had a brief cameo himself). Lipper turned Stone's screenplay into a novel and set out on other film projects, writing the script for City Hall, starring pal Al Pacino. While pursuing his silver screen dreams he also founded an investment firm, Lipper & Co., using his formidable connections to lure a number of media moguls, celebrities and political players as investors.
At its peak, Lipper's fund managed $5 billion and boasted investors like Julia Roberts, Matt Lauer, Mort Zuckerman, Henry Kravis, Jon Tisch, Ed Koch, Danny Aiello, and Michael Eisner. These were good times for Lipper: He traveled in predictably high-powered circles on both coasts, mingled with celebs as a Sundance trustee, and had the ultimate Hollywood trophy sitting on his mantel—he won an Oscar in 1999 for The Last Days, a documentary film about the Holocaust which he produced with Steven Spielberg.
But with Lipper's attention increasingly focused on Tinseltown glory, he took his eye off day-to-day business at the firm, which ultimately proved to be his undoing. In 2002, his convertible arbitrage hedge fund announced it had lost 40 percent of its value—some $315 million—and charges of fraud and mismanagement soon followed. He was eventually forced to liquidate his firm and one of his key fund managers ended up going to prison. Although Lipper himself escaped criminal prosecution, he was forced to hand over millions in fines and legal settlements.
After disappearing for a spell, he returned to the business world when longtime pal Bruce Mosler hired him as executive vice president of real estate giant Cushman & Wakefield. He's since used his contacts to help the firm expand abroad.
Lipper married to Evelyn "Evi" Gruss in 1966; she's a developmental pediatrician at Cornell. The couple had four daughters—Daniella, Joanna, Tamara and Julie—before divorcing in 2000. (Evelyn's brother is Martin Gruss, the father of Josh Gruss, who is married to Shoshanna Lonstein.) Lipper lives in a 5,000-square-foot townhouse on Bedford Street which was constructed by architect Didi Pei, the son of I.M. Pei.