Introducing Fortune’s first annual Leadership Infamy Awards

Updated: Jun 16, 2014 6:47 PM UTC | Originally published: Mar 21, 2014
Photo: Bloomberg\/Getty

The "Shoot First, Think Later" Award

Vladimir Putin, 61, Russian President
Look no further than the week's headlines. The Russian strongman—often photographed as such, shirtless in the Russian wilderness—shrugged off the threat of sanctions and diplomatic isolation when he annexed Crimea, a region of Ukraine, this week. Meanwhile, Putin's government stands accused of sanctioning a litany of human rights abuses—from the persecution of environmental activists and Russia's LGBT community to police brutality and the suppression of speech, religion, and assembly. Sure, "decisiveness" is an admirable quality in a leader—but not when it hastens a string of bad (and possibly catastrophic) decisions.

Photo: ANDREAS SOLARO\/Getty

The "Bunga Bunga" Award

Silvio Berlusconi, 77, Italian media tycoon and former prime minister
A good pal of Putin's (the Russian President once gave him a bed), Berlusconi has used his own craftiness to bring himself business and political success. But, it would seem, his behavior has also brought a great deal of strife to the country he has led three times, for a total of nine years. Italy's economy and government affairs are in disarray—the country has had three Prime Ministers since Berlusconi was booted in 2011. One gets the impression that "Il Cavaliere," as Berlusconi is known, spent most of his time in office, preoccupied with Bunga Bunga, managing the media (a good portion of which he owns), and fending off accusations of bribery, tax evasion, and paying an underage girl for sex. In August an Italian court found Berlusconi guilty of tax fraud, a conviction that was upheld this week by Italy's highest appeals court. Berlusconi, for his part, has repeatedly denied all wrongdoing, noting that his famously bacchanalian parties were just "elegant dinners" marked by "joy, serenity, and conviviality" and that he has been unfairly targeted by prosecutors and judges.

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The "Druglord of the Rings" Award

Joaquín "El Chapo" Guzmán, 56ish, alleged to be a Sinoloa drug kingpin
Thirteen years a fugitive, El Chapo, the world's most-wanted man accused of drug trafficking, was awoken and arrested quietly one morning last month in Mexico. The capture did not live up to his legend, expressed in one narcocorrido: "From his feet to his head, he is short, but from his head up to the sky, I'd say he's the biggest of the big—who could possibly doubt it?" Just five-six and born poor, El Chapo reputedly built an international drug cartel so successful that he made the Forbes billionaire list in 2009. He has been indicted on drug trafficking and various other charges in seven U.S. court districts and faces a slew of charges in Mexico. A coup to law enforcement everywhere, El Chapo's arrest was less celebrated in Sinaloa State, where he had cultivated a Robin Hood-like image among his people and where his control ensured a degree of stability in the region.

Photo: Chip Somodevilla\/Getty

The "If You Build It Badly, They Won't Come" Award

Kathleen Sebelius, 65, Secretary of Health and Human Services
Ownership of the government's healthcare.gov disaster is a bit of a hot potato, but it was under Sebelius's watch as Health and Human Services Secretary—the President's top health official—that the long-awaited Obamacare launch was so badly botched. Sebelius's call for an Inspector General investigation into the contracting and project-management processes (among other things), and her admission that the launch was "flawed," were good steps toward accountability—but too little, too late.

Photo: Alex Wong\/Getty

The "Bully With a Badge" Award

Darrell Issa, 60, U.S. Representative (R-Calif.), Chairman of the House Committee on Oversight and Government Reform
Few give Congress any leadership points these days (see No. 10), but Issa, chair of the House Oversight Committee, may have sunk to new lows earlier this month when he abruptly ended a hearing and cut off the microphone of fellow member Elijah Cummings, a Democrat. Issa came around a couple of days later and apologized to Cummings, but the incident was characteristic of what critics see as the California Republican's blindly partisan approach. No one could accuse the congressman of slacking off—he's certainly made energetic use of his platform to investigate the government. But his nearly single-minded focus on proving that "Obama is one of the most corrupt Presidents of modern times," as he claimed in 2011—a comment he later walked back to suggest that he meant the "Obama administration," not the President himself—arguably comes at the expense of more objective, worthwhile work.

Photo: Bloomberg\/Getty

"The Man Behind the Curtain" Award

Thaksin Shinawatra, 64, former Thai Prime Minister
Deposed in a coup in 2006, Shinawatra, the former Prime Minister of Thailand, now lives in luxurious self-exile in Dubai. His homeland, meanwhile, has been beset by protests and violence, much of it done in Shinawatra's name—and, reportedly, with his financial backing. His younger sister, Yingluck, is now Thailand's Prime Minister—and Shinawatra apparently continues to meddle. It has not helped to calm things down: While his political foes in Thailand aren't blameless or well led either, Shinawatra's almost cultlike influence from afar makes him particularly destabilizing.

Photo: Bloomberg\/Getty

The "Blind Leading the Blind" Award

J.C. Penney board
The board of J.C. Penney (jcp)—which boasted only one director with retail experience—brought in A (aapl)pple retail star Ron Johnson as CEO. Huge score indeed—but then the adoring board signed off on an industry transformation that had never been tested, one that alienated current customers without attracting new ones. The result: $2.4 billion in losses in the past two years. (For the full and extraordinary story, see "How to Fail in Business While Really, Really Trying.")

2014 Miami Beach Police Dept

The "Return to Neverland" Award

Justin Bieber, 20, singer
With more than 50 million followers on Twitter (twtr)—second in popularity only to singer Katy Perry—the baby-faced Canadian pop star is an unquestioned social-media phenom, but he's beginning to lose some of his Beliebers. Or at least set some bad examples for them. In the past few months he's racked up misdemeanor charges all over the map: He was caught drag racing under the influence in Miami, throwing eggs in California, and assaulting a limo driver in Toronto. (Bieber pleaded not guilty to the DUI, as well as to related charges that he resisted arrest and was driving with an expired license; at presstime, no plea had been entered into the egging case, and a pretrial hearing has been set in the Canadian incident for April 14.)
The bratty behavior has been enough to inspire a number of Twitter users to take to the singer's beloved Twitter with the hashtag #DeportBieber—and for one Michigan man to petition whitehouse.gov with a deportation request.

2014 Toronto Star

The "Canada Goose" Award

Rob Ford, 44, Toronto mayor
In 2013, Toronto's 2.8 million citizens learned that their city was in the hands of a man who once smoked crack—but only "probably" in one of his drunken stupors. This was the explanation that Ford offered after first he denied the incident outright; second, an incriminating videotape was discovered; and third, the accusations garnered worldwide attention. Rather than resign, Ford went on Jimmy Kimmel. Yes, strength and stick-to-itiveness can be real virtues—but we're guessing this wasn't the sort of leadership Torontonians had in mind when electing the young Chris Farley doppelgänger their mayor in 2010. At least they found someone who could finally give their ultra-clean town some street cred.

(c) Nathan Blaney

The "Why Bother?" Award

113th Congress
By every reasonable measure, this Congress is going above and beyond to earn its record-low approval ratings. Here's one such measure: Through 2013, lawmakers passed 58 pieces of legislation, the lowest output since 1947. Inactivity doesn't always reflect dysfunction, of course. But even if you're a less-is-more type when it comes to the federal government, it's hard to argue that this Congress's endless partisan bickering—which ultimately led to a nonsensical 16-day government shutdown in October—benefits anybody. There have been a couple of green shoots of comity lately, with the parties managing to forge agreements on a two-year budget and a farm bill. But with the midterms in view, the deadlock will almost certainly get worse before it gets better.