Editor’s Note: Michael D’Antonio is the author of the book “Never Enough: Donald Trump and the Pursuit of Success” and co-author, with Peter Eisner, of the book “High Crimes: The Corruption, Impunity, and Impeachment of Donald Trump.” The opinions expressed in this commentary are his own. View more opinion on CNN.
The question arose the minute federal agents began their search of Rudy Giuliani’s home and office. Once again someone close to former President Donald Trump – someone who could testify against the former president – was in prosecutors’ crosshairs. Once again it seems possible that a Trump friend could flip into an enemy.
We have been here before. In 2018, Trump’s longtime lawyer Michael Cohen saw his home and office raided as part of an investigation into crimes he may have committed on his client’s behalf. Trump signaled his wobbly commitment to when he failed to respond to Cohen’s distress signals as prosecutors were pressuring him. Cohen ultimately cooperated with investigations into Trump’s business dealings and pled guilty to allegations made against him. Following the raid last week, Trump called Giuliani a “great patriot,” and said that the raid had been “very unfair.”
Like Cohen, Giuliani was Trump’s attorney. And like Cohen, his portfolio has included propagandizing on his man’s behalf. Among the infamous lines the former New York City mayor has offered in service to Trump has been, “Truth isn’t truth,” and repeating that the 2020 election was marred by “widespread nationwide voter fraud.” Most recently, Giuliani told the crowd that rallied on January 6 to protest the election, “Let’s have trial by combat.” Later that day, a pro-Trump crowd attacked the US Capitol.
The raids on Giuliani’s home and office appear related to an investigation of Giuliani’s activities in Ukraine in the run-up to the 2020 election. Working with two Soviet-born immigrants to the US, Giuliani had sought Ukrainian help in his effort to dig up dirt about Trump’s political rival Joe Biden.
The tale of Rudy and Donald is best understood by considering their relationship – convoluted in a way that is typical for team Trump’s political machinations. Both rose to fame during the 1980s in New York when Rudy was a publicity-seeking prosecutor and Donald was a publicity-seeking businessman. Trump supported Giuliani’s political ambitions. Giuliani happily enlisted Trump in high-profile stunts, including a filmed sketch in which Rudy donned drag and Trump pretended to sexually harass him.
As Giuliani and Trump built cartoonish public personas, they found it mutually beneficial to support each other. Whether this led to an actual friendship is difficult to say. Trump has often been described as a man with few (if any) actual friendships. Giuliani doesn’t seem to have many more.
In 2020, the former New York mayor forgot to hang up on a Daily News reporter and, thinking he was off the line, complained he only had “five friends left.” For a man who was mayor, this is an astounding confession. It reveals that like Trump, he may be a transactional kind of person; someone who may practice give-and-take but doesn’t really connect.
As CNN reported in 2020, former White House Chief of Staff John Kelly said that Trump was transactional in every relationship he had. This approach, which would see every situation as an opportunity to make a deal of some sort, leaves little room for emotion or empathy. Is Giuliani equally transactional? His effort to remove a lifelong public servant like Ambassador Marie Yovanovitch with baseless accusations, suggests a person who is as coldly calculating as Trump. Both men seem to have trouble with loyalty. And both were Democrats before they became Republicans.
Giuliani briefly signaled the limits of his affection for Trump prior to the first impeachment when he said he had “insurance” that would somehow keep Trump loyal to him. Although he later said this was a sarcastic comment, it created the impression that the former mayor possessed some information that could harm Trump and that this gave Giuliani leverage.
From a distance, it would seem as if Giuliani and Trump now have little mutually beneficial business to transact. Trump doesn’t need Rudy’s political support, and now that he’s out of the White House, he cannot pardon Giuliani for any crimes he may have committed. This may explain why the former mayor’s son Andrew struggled when CNN’s Erin Burnett asked him whether a flip was coming
“No!” he began, but then stammered, “I mean, he has … there is … I don’t really know how to respond to this, because it’s theoretical.”
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The younger Guiliani could say the question was “theoretical” because his father has not been charged and technically faces no imminent prosecution. However, the Department of Justice will be scouring the materials collected during its raids and could bring the kind of charges that would make a defendant eager to tell what he knows.
After the raid, a person close to Trump said, “Even the most loyal people have their breaking point.”
This concern makes even more sense when you consider that Giuliani’s loyalty may have been contingent on business and political transactions that are no longer relevant. From this perspective one has to ask … why wouldn’t he flip?