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.”
Click here to listen to Roy Oppenheim in his own words
“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
This content has been archived. It is available through our partners, LexisNexis® and Bloomberg Law.
To view this content, please continue to their sites.
Not a Lexis Subscriber?
Subscribe Now
Not a Bloomberg Law Subscriber?
Subscribe Now
NOT FOR REPRINT
© 2025 ALM Global, LLC, All Rights Reserved. Request academic re-use from www.copyright.com. All other uses, submit a request to [email protected]. For more information visit Asset & Logo Licensing.
You Might Like
View AllSouth Florida Real Estate Lawyers See More Deals Flow, But Concerns Linger
6 minute readVedder Price Shareholder Javier Lopez Appointed to Miami Planning, Zoning & Appeals Board
2 minute readReal Estate Trends to Watch in 2025: Restructuring, Growth, and Challenges in South Florida
3 minute readTrending Stories
- 1Uber Files RICO Suit Against Plaintiff-Side Firms Alleging Fraudulent Injury Claims
- 2The Law Firm Disrupted: Scrutinizing the Elephant More Than the Mouse
- 3Inherent Diminished Value Damages Unavailable to 3rd-Party Claimants, Court Says
- 4Pa. Defense Firm Sued by Client Over Ex-Eagles Player's $43.5M Med Mal Win
- 5Losses Mount at Morris Manning, but Departing Ex-Chair Stays Bullish About His Old Firm's Future
Who Got The Work
J. Brugh Lower of Gibbons has entered an appearance for industrial equipment supplier Devco Corporation in a pending trademark infringement lawsuit. The suit, accusing the defendant of selling knock-off Graco products, was filed Dec. 18 in New Jersey District Court by Rivkin Radler on behalf of Graco Inc. and Graco Minnesota. The case, assigned to U.S. District Judge Zahid N. Quraishi, is 3:24-cv-11294, Graco Inc. et al v. Devco Corporation.
Who Got The Work
Rebecca Maller-Stein and Kent A. Yalowitz of Arnold & Porter Kaye Scholer have entered their appearances for Hanaco Venture Capital and its executives, Lior Prosor and David Frankel, in a pending securities lawsuit. The action, filed on Dec. 24 in New York Southern District Court by Zell, Aron & Co. on behalf of Goldeneye Advisors, accuses the defendants of negligently and fraudulently managing the plaintiff's $1 million investment. The case, assigned to U.S. District Judge Vernon S. Broderick, is 1:24-cv-09918, Goldeneye Advisors, LLC v. Hanaco Venture Capital, Ltd. et al.
Who Got The Work
Attorneys from A&O Shearman has stepped in as defense counsel for Toronto-Dominion Bank and other defendants in a pending securities class action. The suit, filed Dec. 11 in New York Southern District Court by Bleichmar Fonti & Auld, accuses the defendants of concealing the bank's 'pervasive' deficiencies in regards to its compliance with the Bank Secrecy Act and the quality of its anti-money laundering controls. The case, assigned to U.S. District Judge Arun Subramanian, is 1:24-cv-09445, Gonzalez v. The Toronto-Dominion Bank et al.
Who Got The Work
Crown Castle International, a Pennsylvania company providing shared communications infrastructure, has turned to Luke D. Wolf of Gordon Rees Scully Mansukhani to fend off a pending breach-of-contract lawsuit. The court action, filed Nov. 25 in Michigan Eastern District Court by Hooper Hathaway PC on behalf of The Town Residences LLC, accuses Crown Castle of failing to transfer approximately $30,000 in utility payments from T-Mobile in breach of a roof-top lease and assignment agreement. The case, assigned to U.S. District Judge Susan K. Declercq, is 2:24-cv-13131, The Town Residences LLC v. T-Mobile US, Inc. et al.
Who Got The Work
Wilfred P. Coronato and Daniel M. Schwartz of McCarter & English have stepped in as defense counsel to Electrolux Home Products Inc. in a pending product liability lawsuit. The court action, filed Nov. 26 in New York Eastern District Court by Poulos Lopiccolo PC and Nagel Rice LLP on behalf of David Stern, alleges that the defendant's refrigerators’ drawers and shelving repeatedly break and fall apart within months after purchase. The case, assigned to U.S. District Judge Joan M. Azrack, is 2:24-cv-08204, Stern v. Electrolux Home Products, Inc.
Featured Firms
Law Offices of Gary Martin Hays & Associates, P.C.
(470) 294-1674
Law Offices of Mark E. Salomone
(857) 444-6468
Smith & Hassler
(713) 739-1250