Appearances are everything in the P.R. trade, and Rubenstein appears an exemplar of carefully cultivated civic virtue. Yet anyone familiar with his client list knows that he is just as conversant with civil villainy. That list boasts more subjects of controversy -- tycoons like George Steinbrenner, Ronald O. Perelman, Donald Trump, and Rupert Murdoch; divas Naomi Campbell and Leona "Queen of Mean" Helmsley; companies in crisis like Long-Term Capital Management and Waste Management, Inc.; bite boys Mike Tyson and Marv Albert -- than fill "Page Six" on a good day (and oh, by the way, Rubenstein also represents the New York Post).
Rubenstein's unique reputation as a cultural and political go-between took decades of cultivation. And he has made some very deft moves to sustain it, but none more telling than his switch from dedicated operative for the city's Democratic party to proponent of the ideology of self-interest. He currently supports and raises money for both Rudolph Giuliani and Al Gore, a political position that can truly be said to run the gamut. With such ecumenical political clout and his crazy quilt of clients, Rubenstein can claim to be the key gatekeeper to today's access culture, whoever happens to be in power. "Howard's the consummate survivor," says a City Hall observer. "He's very wily." A pause. "But he's devoid of any principles."
Indeed, Rubenstein has been involved in some singularly vicious tabloid battles. In sports, he is renowned for carrying out the orders of Steinbrenner, who first hired the P.R. man in 1988 during his war against star hitter Dave Winfield. "The Yankees' owner vengefully slimed" Winfield, wrote Tony Kornheiser of the Washington Post at the time; it was charged that the slugger had given Robin Givens's mother venereal disease, and that his charitable foundation was in disarray. "It was 'Destroy Winfield,' " confirms someone privy to Rubenstein's first conversations with Steinbrenner. "I was with him way before that time," Rubenstein says. "He didn't hire me for that reason."
Rubenstein's hand can be seen in many other conflicts that have enlivened the city in recent years -- often on both sides. Though he's a mainstream Jewish leader and longtime adviser to many Hasidic groups, he also represents a radio-station group that has a history of anti-Semitic broadcasts. Though he's known for representing unions, he took the side of the Harvard Club against its striking waiters and busboys. His firm simultaneously represented the Tobacco Institute and a cancer hospital, Leona Helmsley and Donald Trump when they were at each other's throats, and a number of competing educational institutions, including N.Y.U., a longtime account that let him go in a reorganization that happened just after his signing Columbia University as a client.
He's also been accused of raising money for elected officials while at the same time working as a lobbyist for clients who appear before them. But he preempted that criticism by announcing his decision to stop fund-raising at a very public hearing about lobbying elected officials in 1988 where he and clients like the Bernstein brothers (famously the fronts for Ferdinand Marcos) were asked to testify. "We fixed upon Rubenstein as someone with incredible conflicts of interest," says lead lawyer Richard Emery, who came away admiring the P.R. man. But his recent return to fund-raising gives Emery pause. "If that's true, you've got a good story," he says.
It is true: The New York City Campaign Finance Board reports that in 1997, Rubenstein raised money for Giuliani from 24 contributors, including clients Donald Trump, Daniel Tishman, Raoul Felder, and a number of development companies. Rubenstein says that his lobbying is minimal. But City Council-member Kathryn Freed says, "He can still get things done; it's just not as blatant as it used to be."
All of which explains why one competitor has had a field day wisecracking about Rubenstein's modus operandi. John Scanlon, the burly, bearded flack who represented Ivana Trump in her divorce from Rubenstein client Donald, has said Rubenstein "has more conflicts than downtown Beirut," once described him as "the greatest carrier of water on both shoulders since Rebecca at the well," and has been known to joke that Rubenstein's doctor has given him "an ethical bypass."