Jeanine Pirro

Pirro is Westchester's former district attorney, a perpetual candidate for political office, TV personality, and walking trainwreck.

Jeanine Ferris earned her J.D. at Albany Law School and went to work as an assistant DA in Westchester County in 1978. She soon convinced her boss to let her set up the county's first domestic-violence unit, and spent the next few years prosecuting offenders and crusading for reforms to protect battered wives and kids, activities that began to generate the public profile she so desperately sought. She used her burgeoning notoriety to mount a 1986 campaign for lieutenant governor, but later aborted the bid after her husband's ties to organized crime came under scrutiny—the first of many wrenches Al Pirro would throw into her political career. In 1990, she was elected to a county judgeship, and then won the election for the Westchester DA job in 1993. Her talking-head career got a jumpstart during the O.J Simpson trial when she, her tough-talking rhetoric, and her cleavage-bearing ensembles became regulars on Larry King Live, Rivera Live, and like-minded cable fare. She remained a fixture on the cable circuit for more than a decade while also serving as Westchester's DA, stirring up headlines on a near weekly basis thanks to the aggressive prosecutions of pedophiles, rapists, and other sexual deviants. Her accomplished (if tawdry) record and taste for the spotlight soon made her a star in state Republican circles and an obvious choice for higher office in New York.

In 2005-06, Pirro endured two of the most disastrous, gaffe-plagued, scandal-ridden campaigns in state history—and she did it all in the span of a single election cycle. First she ran against a href="../../../profiles/hillary-clinton" class="profile-link">Hillary Clinton for her U.S. Senate seat. Things immediately got off to a bad start—while announcing her candidacy, she lost a page of her speech and paused for an excruciatingly embarrassing 32 seconds. As months went by and Pirro's missteps piled up, high-profile New York Republicans like George Pataki encouraged her to drop her candidacy and make way for a Republican who stood a fighting chance. In December '05, Pirro finally obliged and instead threw her hat into the race for Attorney General against Democratic nominee Andrew Cuomo. She trailed Cuomo in the polls from the start, but her candidacy was really done in by an eleventh-hour federal investigation into her abuse of power during her time as DA: She was accused of asking Bernard Kerik to help her use state resources to spy on her husband, whom she (rightly) suspected of cheating on her. Cuomo handily defeated her in the election. Since the twin cataclysms that were her two campaigns for higher office in 2006, Pirro has attempted to stage a comeback with a legal TV show; despite numerous delays, Judge Jeanine Pirro debuted on the CW in 2008, and earned her a daytime Emmy in 2011. [Image via Getty]