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The Worst Lawyers of the Year Awards

Vivia Chen

December 27, 2020



While everyone else in legal media is busy compiling names for the best lawyers for the year—litigator, dealmaker or otherwise—I have a list that’s much more fun and illuminating: the very worst of our esteemed profession. And now I’m ready to share!

Most ridiculous/goofiest lawyer: Rudy, Rudy, Rudy. What’s your favorite Rudy Giuliani moment for 2020? Was it the time when hair dye/ink/steak sauce dripped down his cheek as he faced reporters after the election? Or when he railed incoherently about stolen votes at the Four Seasons Total Landscaping company (nestled between a porn shop and a crematorium)? And let’s not forget his star turn in the new Borat movie, in which he turned his avuncular attention to a young woman. Yuck.

Most unscrupulous, inscrutable lawyer: Bill Barr. He’s dangerous because he knows what he’s doing, even if no one understands his endgame. Until very recently, Attorney General Barr was essentially President Donald Trump’s personal consigliere. Barr’s top hits included distorting the Mueller report, sabotaging DOJ’s own sentencing recommendations against Roger Stone and dropping charges against Michael Flynn (even though Flynn had pleaded guilty). And just last month, Barr demanded that the DOJ investigate claims of voter fraud.

Now, all of a sudden, he’s a born-again believer in the rule of law, declaring that there’s no evidence of election fraud, siding with intelligence reports on Russia’s cyberattacks against U.S. institutions and refusing to appoint a special prosecutor to go after Hunter Biden. Is Barr now just another rat abandoning a sinking ship?

Most fraudulent lawyer: Jenna Ellis. If Ellis (pictured above with Giuliani) can style herself as a constitutional lawyer, I’m a shoo-in for the Nobel Prize for literature. How does someone who’s been handling traffic disputes, domestic abuse cases and other local matters suddenly become the go-to lawyer (along with Rudy) for a sitting president in his effort to overturn the election? One word: chutzpah. Another word: liar. (Not only has she never come close to handling a constitutional dispute, her name isn’t even listed on any federal case, reports The Wall Street Journal). And you thought women always underestimate themselves!

Most shameful Harvard Law School grad: Ted Cruz, Ron DeSantis and Mike Pompeo. It’s an embarrassment of riches (or just embarrassment) for the esteemed law school that so many Harvard Law alums can claim this title. The three standouts: Florida Gov. DeSantis, for refusing to acknowledge the seriousness of COVID-19; Texas Sen. Ted Cruz, for his general shamelessness, including his eagerness to argue the spurious election case brought to the U.S. Supreme Court by Texas Attorney General Ken Paxton; and Secretary of State Mike Pompeo, for doing nothing except being Trump’s henchman. (Remember how Pompeo joked that the election results would be ignored? “There will be a smooth transition to a second Trump administration,” he said cutely.)

800px-Kayleigh_McEnany_(39645264535)_(cropped)Most embarrassing Harvard Law School graduate under 40Kayleigh McEnany. White House press secretary McEnany (right) is the clear winner because she spews nonsense with scary alacrity. (She describes herself as “that blond girl passionately advocating for then-candidate Donald Trump proudly wearing my gold cross” in her 2018 book. Yeah, she wrote a book.) And she’s still at it, insisting that the Electoral College vote for Joe Biden was just “one step in the constitutional process.”

Ken_PaxtonMost transparently corrupt lawyer: Ken Paxton. The Texas attorney general knew damn well Texas had no standing to challenge the presidential votes in Michigan, Wisconsin, Georgia and Pennsylvania. Indeed, the Supreme Court wasted no time in dismissing the case. But Paxton (on left) brought the lawsuit, spent God-knows-how-much of taxpayers’ money on it, and got Trump’s attention. And now he’s hoping for that presidential pardon he desperately needs after eight of his top officials accused him of bribery and abuse of public office in connection with campaign donations.) How is it possible this guy hasn’t been run out of town? OK, it’s Texas.

440px-Rod_Rosenstein_official_portrait_2Wolf in sheep’s disguise: Rod Rosenstein. He seems bland—milquetoasty—but perhaps thoughtful behind those owlish eyes. Largely harmless. That was my impression of Rod Rosenstein when he labored as deputy attorney general under Jeff Sessions, then Bill Barr. But this year we learned this from the New York Times: Rosenstein pushed the limits on Trump’s zero-tolerance immigration policy, “telling the five prosecutors that it did not matter how young the children were. He said that government lawyers should not have refused to prosecute two cases simply because the children were barely more than infants.” Chilling. And the coda? Rosenstein (another Harvard Law grad) is now a partner at King & Spalding, where, ironically, famed anti-Trumper Sally Yates is also a partner. I wonder if they chat about the good old days by the espresso machine.

Cleta_Mitchell_by_Gage_SkidmoreWackiest Big Law partner: Cleta Mitchell. Though most Trump supporters in Big Law tend to keep a low profile, Foley & Lardner partner Cleta Mitchell (left) is going all out for her man. First, she claimed on Fox News that dead people voted in the presidential elections. Then, in another Fox show, she was so insistent that Biden didn’t win that Fox anchor Sandra Smith grimaced in disbelief. Later, Mitchell doubled down, tweeting: “Sandra Smith thinks FoxNews calling the election means Biden is President. Forget that pesky Constitution … happy to be considered a nut job because I believe in the rule of law.” What a way to put Foley & Lardner on the map!

1024px-180720_KimberlyGuilfoyle_248_wiki_(cropped)-1Loudest and most exhausting lawyer: Kimberly Guilfoyle. Ex-prosecutor, ex-Fox News commentator and Donald Trump Jr.’s current consort, Kim Guilfoyle (on right) delivered a hard-to-forget speech at the Republican National Convention this summer. It wasn’t so much what she said but how she said it—yelling, screaming, throttling. And her talents go beyond oration: According to Politico, she’s offered lap dances to big Trump donors. Honestly, I’m out of breath just writing about her.

440px-Jeffrey_toobin_2012Dumbest lawyer: Jeffrey Toobin
. Hands down (no pun intended), the CNN commentator and New Yorker writer wins this year’s self-inflicted wound award. As you’ll recall, Jeff Toobin (another Harvard Law grad) was caught on Zoom masturbating in front of his New Yorker colleagues—albeit unintentionally. And just like that his career vanished.

Who’s your favorite worst lawyer from the past year? By all means, drop me a line.



[email protected]   Twitter: @lawcareerist


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Two thoughts:

1) You forgot to include Jeff Sessions, Lin Wood, and Sydney Powell; and

2) Tell us all again why Harvard Law is such a fine institution that honest competent lawyers everywhere are supposed to feel inadequate in the face of her alumni.

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About The Careerist

The Careerist takes an inside look at how lawyers shape their careers and manage their lives. The blog aims to dissect developments in the profession, provide useful information and advice, and give lawyers a platform to voice their views. The goal is to provide a fresh, provocative take on the state of lawyering.

About Vivia Chen

Vivia Chen

Vivia Chen, The Careerist's chief blogger, has been covering the business and culture of law firms for a decade. A former corporate lawyer, Chen is fascinated by those who thrive (as well as those who don't) in the legal profession. Her take: Success in the law (and life) doesn't always travel a linear path. If you have topics you'd like to discuss or information to share, contact her: [email protected]

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