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The mayor's prospective pick for corporation counsel has a storied legal history—including this lawsuit, which has yet to come up in the conversation around his nomination.

Randy Mastro speaks as Mayor Eric Adams Launches NYC Legal Fellows Program. City Hall. November 2, 2022.
(Caroline Willis / Mayoral Photo Office)

Randy Mastro, a "legal pitbull" and Giuliani City Hall alum, is currently fighting to become New York City's top lawyer, a position where he would defend Mayor Eric Adams and other City officials and employees in civil court. His critics, including City Council members who have vowed to oppose his appointment, have pointed to his extensive case history as the reason he shouldn't assume the role of corporation counsel. Amazon, former New Jersey Governor Chris Christie in his Bridgegate era, current New Jersey Governor Phil Murphy in his anti-congestion pricing crusade, Bear Stearns, Chevron, and JP Morgan have all had the distinct and well-documented pleasure of being represented by Randy Mastro. But there's another old client of Mastro's that should make people pause—the conservative thinker and failed Supreme Court nominee Robert Bork.

In June 2007, Bork slipped and fell off a podium at a Yale alumni social club event where he was supposed to be a speaker. Almost a year later, in May 2008, he settled a $1 million dollar lawsuit against the club for injuries to his head and one of his legs—or, as the New York Post put it at the time, "BONKED BORK SETTLES SUIT." The lawyer who led him to victory and an undisclosed amount of cash? None other than Mastro. 

Bork was, to put it extremely mildly, a controversial figure in U.S. politics. In the '60s, he pioneered the theory of original intent. In the '70s, he played a bit part in the Watergate scandal via the "Saturday Night Massacre" and spent five years as a Court of Appeals judge. In 1987, President Ronald Reagan tapped him as the next Supreme Court justice—but his nomination was defeated by liberal opposition in Congress led by Senator Ted Kennedy, who said that "Robert Bork's America is a land in which women would be forced into back-alley abortions, blacks would sit at segregated lunch counters, rogue police could break down citizens' doors in midnight raids, and schoolchildren could not be taught about evolution."

As to why Mayor Adams might want a man like Mastro—who represented a conservative thinker like Bork, one that argued against the use of contraception in marriage, working mothers, and the desegregation of businesses—in his administration's corner, one only has to look at the state of the legal threats facing Adams and his top aides, like Timothy Pearson and Winnie Greco: Adams wants the best and most aggressive litigators on his side, and that's how he sees Mastro, ideology be damned. (As the New York Times noted, Mastro, if appointed, would likely work with Alex Spiro, the  high-profile "celebrity" attorney that the mayor has plucked to defend him against an accusation of sexual assault.) Nevermind the aforementioned fact that Mastro is representing New Jersey Governor Phil Murphy's bid against the City's new congestion pricing regulations, or that as of this week, Mastro is representing landlords (again)—this time, in a bid against New York state's rent stabilization laws

Will Mastro emerge victorious, like Bork? Or will he meet defeat at the hands of liberal politicians, like Bork? Multiple caucuses and members of the City Council have already expressed that they really, really don't want him in the role. Although Mastro hasn't even been officially nominated, the council's Progressive Caucus pledged to oppose his confirmation on the day news broke that he was likely being considered for the role, and nine days later, both the LGBTQAI+ Caucus and the Black, Latino, and Asian Caucus had followed suit. Still, City Hall appears to remain supportive, if noncommittal: Last week, the mayor declined to comment directly on the lawyer's potential nomination, but his chief counsel, Lisa Zornberg, called Mastro "an incredibly top-notch, world-renowned lawyer."

Only time will tell if the confirmation process delivers Mastro a spot in the Adams administration…or a metaphorical bonk.

Some links that aren't such a blast from the past: 

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