A Look Back At Hillary Clinton's Legal Issues

"Crooked Hillary" was an unfortunate epithet bestowed upon the former Secretary of State by her rival for the 2016 presidency. But, over her many decades in public life, Hillary Clinton's career has been defined as much by the long list of legal challenges she has faced as by her many impressive political achievements. The Whitewater debacle of the late 1970s threw Hillary in at the deep end right off the bat. Essentially, a misjudged property venture saw Hillary's $1,000 investment grow into nearly $100,000, and many wondered if this was an insider favor due to husband Bill Clinton's position in government. Their business partner in the project, James McDougal, was subsequently convicted of fraud. 

While the Clintons were never personally charged themselves, the political power couple's involvement provided ample ammunition for their opponents. Hillary's time as Secretary of State offered little relief, especially not after the infamous 2012 Benghazi attack. A terrorist raid on the U.S. consulate in Libya prompted heavy congressional hearings about how she mishandled the crisis. Hillary survived a grueling 11-hour testimony in front of Congress, and they ultimately found no criminal evidence, but it gave critics plenty of room to jump on the embittered anti-Hillary bandwagon.

Perhaps no legal issue cast a darker shadow over the presidential candidate's political career than the disastrous emails controversy. Hillary's use of a private server during her time as Secretary of State later triggered a highly-publicized FBI investigation. Again, no charges were filed, but the ordeal dramatically mired her run in 2016 against Donald Trump, who seized the opportunity to stoke further accusations of crookedness.

Hillary Clinton was unceremoniously thrust back onto the legal battlefield in 2020, when former congresswoman Tulsi Gabbard sued her for defamation for a staggering $50 million. In a now-deleted episode of David Plouffe's "Campaign HQ" podcast, Clinton described the primary hopeful as "the favorite of the Russians" who she asserted "have a bunch of sites and bots and other ways of supporting her so far," (via Politifact). Gabbard, almost pantomime-like in her response, lashed out on X: "You, the queen of warmongers, embodiment of corruption, and personification of the rot that has sickened the Democratic Party for so long, have finally come out from behind the curtain" before filing the suit against her. It should come as no surprise that Gabbard eventually dropped the legally tenuous case, with a spokesperson for the former Secretary of State decrying it as "a publicity stunt through and through," per CNN. 

Of course, Donald Trump has long proven he can't resist the chance to take a swing at Clinton. Long after his victory in 2016, he filed a lawsuit in 2022 accusing her, along with several others, of orchestrating a conspiracy to derail his campaign with allegations of Russian collusion. Trump's plan backfired when the case was dismissed outright. According to court documents, the judge ultimately said that it "should never have been brought" in the first place and slammed it as "completely frivolous, both factually and legally." Trump was ordered to cough up almost $1 million for all the time wasted. As it turns out, using the justice system to score political points isn't exactly a winning strategy.