Roy Oppenheim Represented the Downtrodden — And Made a Good Living Doing It
"I was quoted at one time as saying that ... foreclosure defense is the bottom of the barrel," Oppenheim said. "Lower than being a divorce lawyer."
March 02, 2018 at 03:26 PM
5 minute read
Meet Roy Oppenheim, a onetime Wall Street lawyer who rose to fame doing work he once considered “bottom of the barrel.”
Oppenheim emerged as one of the most prominent Florida foreclosure attorneys in the last decade when he pioneered defenses for property owners facing lawsuits by lenders. In those days, mortgage companies had the upper hand: Borrowers in default on their loans had few, if any, viable legal explanations.
Plus, what motivation did attorneys have to work on behalf of clients who were unlikely to be able to afford legal fees?
“You're going to do well, especially when the banks pay your fees,” Oppenheim said.
But these days, Oppenheim concedes he “made a good living” from foreclosure defense. During a recent ski vacation, he said the practice area was fertile ground for skilled litigators who could defeat plaintiff lenders.
“I was quoted at one time as saying that … foreclosure defense is the bottom of the barrel,” Oppenheim said. “It's … lower than being a divorce lawyer.”
“You'd go into a cocktail hour (and say), 'How are you? I defend homeowners in foreclosure,' and people would sneer at you,” the Princeton University alum said. “I remember going up to Harvard and being with some law professors up there who I'm friends with, and they would say, 'How do you get paid? I don't understand.' ”
Before he started his Weston law firm with his wife, Ellen Pilelsky, in 1989, Oppenheim's resume shows he worked in New York for Milbank Tweed Hadley & McCloy and in Miami for White & Case — law firms that represented multinational corporations and wealthy clients like former First Lady Jacqueline Kennedy Onassis.
Oppenheim continued to pursue that clientele for his own business and found a lucrative niche market, representing developers, lenders and investors in what was then a thriving South Florida market. Around that time, he co-founded Weston Title & Escrow and built a practice on real estate financing and trading.
But his business, the real estate sector and the entire U.S. economy collapsed in the housing market crash of 2008.
“We all know what happened,” Oppenheim said. “Everything we were previously doing — in representing developers and builders and refinancing — all that stopped. It stopped on a dime. And one day you'd come into my office, and instead of it being crazy and phone ringing and everyone running around, it was like a morgue. And you could hear … a penny drop on the carpet.”
It was a frightening experience. During that time, Oppenheim flirted with personal financial disaster as financial institutions holding his money market accounts and other investments teetered on the brink of collapse.
Oppenheim said his small law firm was determined to retain all 12 staff members, including three lawyers, as unemployment spiked to record levels across the country. That decision proved fortuitous because soon Oppenheim would need more than twice as many employees to handle the unexpected flood of business coming his way.
“People just started to wander in: people from the community, from my synagogue, friends. And they said, 'Listen. We're … being laid off or being fired,' ” Oppenheim recalled. “ It was unbelievable the … array of people that we were representing.”
By the height of the foreclosure crisis in 2010, Oppenheim Law was up to eight lawyers and a total of 25 staffers. By then, foreclosure work had lost its stigma, drawing unlikely practitioners.
“What I found really funny is that top firms like Greenberg (Traurig), Akerman … and a whole bunch of other firms ended up doing foreclosure prosecution on a bulk basis,” Oppenheim said. “All of a sudden … all the mighty had fallen.”
The practice he once saw as a “fall” propelled the Ivy Leaguer to national fame, thanks to appearances in Law.com publications, HuffPost Live, FOX News, Lifetime television, Yahoo! Homes, USA Today and The New York Times.
Facing off against Big Law, Oppenheim and other defense attorneys sharpened their litigation skills and uncovered a slew of faulty financial documents created as lenders traded vast volumes of real estate debt on the secondary market. Flawed promissory notes, unsigned notes, faulty assignments and other missteps helped tip the litigation in favor of homeowners.
“For us, that actually just … gratified us because now we were dealing with other lawyers, competent Wall-Street-type lawyers, … good, white-shoe firms,” Oppenheim said. “We could battle it out with them, and then when we won, we felt good.”
Roy D. Oppenheim
Born: New York, 1960
Spouse: Ellen B. Pilelsky
Education: Northwestern University, J.D., 1986; Princeton University, A.B., 1982
Experience: Co-founder and senior partner, Oppenheim Pilelsky, 1989-present; Founder and president, Weston Title & Escrow Inc., 1994-present; Board member, Catalina Lighting Inc., 1999-2000; General counsel, Shopsmart Inc., 1989-1994; Associate, White & Case, 1987-1990; Summer associate/associate, Milbank Tweed Hadley & McCloy, 1985-1987
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