Lawyer Who Contested Duke Estate Is Silver’s Green Party Opponent

His youthful face illuminated by the glow of red lights and scented candles, Raymond Dowd crouched on the floor of his Lower East Side apartment as some 40 members of New York’s nascent Green Party milled about in his living room to raise money for the party’s presidential candidate, Ralph Nader. Presidential fund-raisers usually are held in ballrooms and feature a variation on the theme of rubber chicken. This one had a keg of beer.

Mr. Dowd, a crisply dressed, clean-cut 35-year-old lawyer, seemed out of place in his own apartment, surrounded as he was by the rumpled shirts and shaggy hairstyles of the upstate farmers, political misfits and well-preserved hippies who constitute the rank and file of the Green Party. Mr. Dowd, who came to prominence several years ago for his role in the battle over the estate of Doris Duke, would have fit in at a party celebrating the models and fashion executives who comprise his glamorous client list.

Mr. Dowd grinned broadly as an organic farmer in a Hawaiian shirt challenged former Munsters star “Grandpa” Al Lewis for the party’s endorsement for U.S. Senate, promising to use his time in office to combat the use of pesticides and irradiated meats. After the speech, Mr. Dowd rose to thank the farmer for his comments and for the organic salad he’d brought. Before introducing the next speaker, Mr. Dowd seemed to remember that he was supposed to make an announcement.

“Oh, yeah,” he said matter-of-factly. “I’m running for the Assembly against Sheldon Silver.”

The crowd burst into applause and whoops of delight. If Mr. Dowd’s coupling with the eclectic New York Greens might be called odd, then his decision to take on State Assembly Speaker Sheldon Silver would seem to be downright extraordinary, if not foolhardy. Mr. Silver, an old-fashioned deal maker who frequently holds court in a back room of Ratner’s restaurant, has been one of the state’s most formidable political leaders since the early 1990’s. He crushed a recent challenge to his authority from rival Democrats by ruthlessly slashing the staff, office space and party titles of key insurgents. Since taking over the speaker’s post in 1994, Mr. Silver has easily fended off token challenges in his overwhelmingly Democratic district on the Lower East Side.

Mr. Dowd’s casual approach to the gargantuan task that awaits him is consistent with the role that he has played to great effect throughout his legal career: the cheerful kamikaze. That is, he seems to relish establishment opposition and long odds.

“Shelly Silver is damaged goods,” Mr. Dowd calmly explained. “He has this imperious style that is half coward and half bully. It’s a kind of politics that will only get you so far. I mean, I’m not afraid of him. What’s he going to do to me?”

Fearlessness aside, there may be more to Mr. Dowd’s seemingly quixotic campaign than is first apparent. The way he sees it, Mr. Silver is vulnerable this year. He points out that Mr. Silver has gotten enormous amounts of negative publicity for the heavy-handed manner in which he crushed the Democratic Party revolt in the Assembly. That uproar came close on the heels of Mr. Silver’s decision to support a repeal of the city’s commuter tax, a purely political move designed to counter Republican Party posturing on the issue. And Mr. Silver’s opposition to a proposed increase in the minimum wage for tip earners, his support for the death penalty and his approval of longer sentencing for drug offenders, according to Mr. Dowd, offers evidence that Mr. Silver has abandoned his liberal and largely poor constituency to curry favor with suburban and upstate Democrats, an important bloc for a downstate speaker who wants to keep his job.

So Mr. Dowd has targeted labor groups, local newspapers and business owners for support, and he has begun assembling a volunteer network of local bartenders, deejays and friends in the advertising industry to help him get exposure.

For their part, Mr. Silver’s aides seem unconcerned about Mr. Dowd. Judy Rapfogel, Mr. Silver’s chief of staff, said confidently that “with the Speaker’s record … we are confident that he will withstand any challenge.” She specifically mentioned the Speaker’s battle to fund a full-length subway under Second Avenue and his efforts to fund education and health care.

Upstart From Fordham

Not that he’s lacked for attention in the past. Mr. Dowd first made waves in the Duke case, where he represented some former domestic employees who were making claims against the corporate executors of the Duke estate, U.S. Trust Company. Throughout the proceedings, the relatively inexperienced Mr. Dowd–an upstart graduate of Fordham Law School–delighted in torturing the white-shoe attorneys opposing him as he mixed highly insulting personal attacks in the courtroom with an endless stream of motions that tied them up in paperwork. In the process, Mr. Dowd accused the estate lawyers, their clients and the New York State Attorney General of corruption for their roles in the affair.

In the end, Mr. Dowd’s clients had little to show for their troubles. Yet the case was fought at huge expense to U.S. Trust, which at one point had to forfeit control over more than $1.2 billion as a result of Mr. Dowd’s arguments.

Thanks to his unusual methods of arguing points of law, Mr. Dowd will likely have no shortage of critics as he attempts to enter the public sector. “I can’t imagine what the hell he thinks he’s doing now,” said Tom Barr, a retired partner from the white-shoe law firm of Cravath, Swaine & Moore who argued against Mr. Dowd in the Doris Duke case. “He’s just not a serious person. He doesn’t know what he’s doing. This guy is a fly-by-night lawyer and a self-promoter. He represents non-clients in a non-way. I’d be surprised if he were representing any serious clients now.”

In the years since the Duke case, though, thanks in part to contacts he made studying and working in Paris and Milan after graduating from Fordham, Mr. Dowd has been able to amass a client base that includes some of the most prominent fashion industry people in New York, including photographer Markus Klinko and designer Rebecca Danenburg. And in that most competitive of sectors, it seems, his confrontational style has found a more appreciative audience.

“The guy is a very aggressive lawyer but at the same time is an excellent deal maker,” said Paolo Zampolli, president of ID Models. “He has been taking care of me since I came to New York and is one of the few people that I trust with my eyes closed.”

Katia M. Sherman, managing director of Major Models, was equally effusive. “He’s been a mentor to me,” she gushed. “He’s made me who I am, almost groomed me by helping me to understand everything. He’s been more like a right arm than a lawyer.”

But it was a distinctly unglamorous case that drew Mr. Dowd, who describes himself as having been “a vague Democrat,” into his current political adventure. He brought a lawsuit against the city Campaign Finance Board over a financing dispute involving the Green Party and a City Council campaign in Brooklyn in which his brother, Michael, served as treasurer. As with the Duke case years earlier, Mr. Dowd waged an aggressive argument against what he regarded as “the unbelievable arrogance” of officials who he felt had stacked the deck against his client. Again, he has had little to show for his efforts: His initial motion was denied and he is currently preparing to go to trial. But he became a wholehearted convert to the Green Party cause.

‘An Absurd Argument’

Laurence Laufer, who acted as counsel for the Campaign Finance Board, admired Mr. Dowd’s spirited handling of the Green candidate’s cause, even as he dismissed Mr. Dowd’s legal reasoning as deeply flawed. “They had an extraordinarily weak case,” said Mr. Laufer, “but Dowd had extraordinary enthusiasm in bringing it. I think they misunderstood the city campaign finance law and I happen to think they made an absurd argument. But he did the best he could with a fundamentally weak case on the facts and law. He was a nice guy and an enthusiastic young attorney.”

On June 17, his first official day of campaigning, Mr. Dowd set off for a Lower East Side street fair armed with several dozen brochures that he had just folded at a table in the air-conditioned Lotus Club restaurant on the corner of Clinton and Stanton streets. It was a hot, humid late-spring day. His confidence was particularly high, as he had fulfilled an important campaign requirement earlier in the day by finding seven of the 37 local members of the Green Party to sign his petition to appear on the ballot. On his way to the fair, as he strolled along the baking sidewalk in rolled-up khakis, a dress shirt and sandals, he began practicing his line of attack.

“Silver’s the ultimate welfare queen,” Mr. Dowd said happily. “He’s getting paid while there are rats crawling around in the garbage outside, and in the playground by the school across the street from my apartment. What’s he done for this district? Where’s Shelly?”

He continued walking, riffing on his opponent. “He’s just doling out pork and fixing the game. He’s getting chummy with Republicans. He’s pro-death penalty, and just shoves young people off into prison, not caring about after-school programs, not educating them and then locking them up when they get in trouble. His politics is to instill fear: ‘Crack addicts will eat your children if you don’t vote for me.’ “

At a crosswalk on Delancey Street, he approached a tough-looking cyclist. “Hey, buddy, would you like to join the Green Party?” The biker, who lived in Williamsburg, said that he liked the Greens and wished Mr. Dowd luck.

“I’m running against Sheldon Silver,” Mr. Dowd told a jogger doing his stretches. The runner looked puzzled. “He’s the assemblyman for this district.” The young man nodded and carefully scanned the Green Party leaflet emblazoned with the group’s “key values,” including feminism, ecological wisdom and social justice. “So have I got your vote?” asked Mr. Dowd. “You got it, man,” the runner assured him.

Walking and talking again, Mr. Dowd summarized his game plan. “It’s going to be very simple: meeting people, shaking hands, and just finding people as pissed off and disenfranchised as I am who will say, ‘It’s time for change.’ “

Mr. Dowd arrived at his destination, the intersection of Grand Street and Essex, and stopped short. For the first time all day, he was at a loss for words. The road was almost completely empty, with no sign of any sort of street fair. Two pedestrians walked by, keeping to the shady part of the sidewalk. A car radio played salsa in the distance.

Undaunted, Mr. Dowd wheeled around and began walking back along Grand Street towards the heart of the district he hopes to represent. “As you can see,” he said, “I need a scheduler.”