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  • Writer's pictureMario Nicolais

A Tale of Two Lawyers

During the winter of 2006, Ted Olson helped me land a job with Rudy Giuliani’s fledgling presidential campaign. Friends for decades, a good word from the legal titan Olson all but assured me a spot in the Lower Manhattan headquarters for Giuliani.

More than ten years later, both found their names linked to the defense team for current President Donald Trump. The two took divergent paths and, given a little background, that speaks volumes about the direction of Trump’s legal strategy.

Giuliani needs little introduction. The hard-charging, pugnacious character seemingly born directly from the incarnate soul of New York City, campaign staff referred to him simply at “The Mayor.” While controversial in his approach, he changed the direction of America’s most prominent city and guided many of us through the defining tragedy of a generation. A law-and-order Republican, fiscal conservative, and social moderate, I came within a telephone call of dropping out of college to join his 2000 U.S. Senate campaign before he dropped out over health concerns. I jumped at the chance to work for him right out of law school. I later took immense pride to see my name alongside his on an amicus brief supporting marriage equality.

Before any of that, though, Giuliani had been a great lawyer. He served Associate Attorney General under the Reagan Administration, the third-highest position in the Department of Justice. In 1983, he “demoted” himself to U.S. Attorney for the Southern District of New York, the single most high profile prosecutor in the country. Simply put, before Giuliani became a household name he had a legal career most attorneys could only dream about having.

If Giuliani was a great lawyer, Olson is giant in the legal profession. Olson served as an Assistant Attorney General for the Office of Legal Counsel alongside Giuliani during the early 1980’s – a post that solidified their friendship. He argued and won the landmark Bush v. Gore case and went on to become Solicitor General of the United States under President George W. Bush. He has since used his legal clout as a leading advocate for the equal protection of gay men and women. Olson is the kind of lawyer who may have more impact on the country’s laws than some members of the Supreme Court.

Bound by their legal careers and partisan politics, the two were forever cemented by September 11th. As Giuliani calmly presided over a city in anguish, the tragedy struck Olson personally. His wife, Barbara died onboard the plane that hit the Pentagon. As the New York Times reported, one of the only private moments Giuliani had that day came when he called a grieving Olson and wept with him.

Given their histories, it is no wonder Trump turned first to Olson and then to Giuliani for help as his legal team imploded. Touting a long and continuous career as a pre-eminent attorney, Olson could have instantly given Trump’s team an injection of gravitas. However, Olson declined noting that the situation around Trump was “turmoil, it’s chaos, it’s confusion, it’s not good for anything … beyond normal.” Remember, these are the words of a man who once spent months analyzing hanging chads.

Into the breach stepped Giuliani. Decades removed from day-to-day legal work — I assume most of Giluiani’s role at various law firms involved his Rolodex, celebrity, and television appearances — it shouldn’t be a surprise that Giuliani pivoted to the closest, most friendly camera rather than preparing for the courtroom. It also shouldn’t be a surprise that he immediately upended the entire legal strategy and undermined Trump’s previous positions.

Whether Giuliani’s presence ultimately asphyxiates Trump’s legal defense or whether it finally speaks to the president in the only language he understands, television ratings, it seems like a desperate gamble. However, when a sure thing like Olson turns you down, it might be a necessary gamble.

Mario Nicolais is an attorney and Denver Post columnist who writes on law enforcement, the legal system and public policy. Follow him on Twitter: @MarioNicolaiEsq

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