Clayton Kershaw Joins These Superstars in Getting Title Monkey Off Their Backs

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Sports can be weird and unpredictable. If the Rays had won Games 6 and 7, Clayton Kershaw would have entered his 14th MLB season with a monkey on his back: that he hadn’t won a World Series. But that’s now how it played out last night. In a game in which he did not throw a single pitch, Kershaw shed his monkey.

I’m really not interested in debating whether Kershaw pitched well enough to win previous playoff games if only he’d gotten some run support from his teammates. Kershaw does have a history of choking in the biggest games. In the 2018 World Series against the Red Sox, Kershaw threw 11 innings and gave up nine earned runs. The Dodgers lost both games he started. These are facts, but at this point, these facts may be irrelevant.

We in the media have created the narrative that there are some stars who cannot perform when it matters most, so I always enjoy when players or coaches who allegedly could not win the Big One transcend that Sisyphean mountain. Kershaw joins these other elite talents:

Michael Jordan: Because it happened in the halcyon days before we were online all day, we may have forgotten that because MJ couldn’t get past the Pistons, newspaper writers from coast to coast opined that he wouldn’t win the big one. After that, his Bulls went on a tear, winning six titles in eight years. We remain grateful to The Last Dance for reminding us about all the Jordan doubters.

John Elway: Elway did not win a Super Bowl until his 15th year in the league. He was 37 years old when the Broncos finally got over the top by beating the Packers. Elway may have had an overall 7-7 postseason record, but he went 7-0  in his final two postseasons.

Peyton Manning: Most people probably remember this one. Peyton Manning lost his first three playoff games and was 3-5 in the postseason before the Colts broke through in 2006-07. While Manning didn’t have to wait as long as some of the others on this list, he was definitely under a microscope in his eighth season in the NFL because the Colts could not seem to get by Tom Brady, Bill Belichick and the Patriots. The eighth time was a charm for this Manning apparently.

Alex Rodriguez: A-Rod actually had pretty good stats in two postseasons with the Mariners. He then spent a few years on the Rangers without making the playoffs, followed by a number of poor October performances in NY with the Yankees. That all changed in 2009, when A-Rod hit .365 with a 1.308 OPS. It was his 15th season in MLB.

LeBron James: LeBron did not have an outstanding team around him in his first tenure with the Cavs, and his passive performance in Game 6 of the 2010 Eastern Conference Finals against the Celtics led many to question his commitment to winning. After taking his talents to South Beach, LeBron and the Heat faded in the NBA Finals against the Mavs. However, the Heat beat the Thunder in 2012, giving LeBron a title in his ninth season in the league.

Andy Reid: The rest of the entries on here are players, and there are probably lots of coaches and managers who belong on this list. However, Reid is fresh on my mind given that the Chiefs are defending Super Bowl champions. It took him 21 years as an NFL head coach to slay the dragon, and I was just as happy for him as I was for Kershaw, if not more.

Who are your favorite athletes or coaches who struggled with adversity before winning their first title? Sound off in the comments.

Written by Ryan Glasspiegel

Ryan Glasspiegel grew up in Connecticut, graduated from University of Wisconsin-Madison, and lives in Chicago. Before OutKick, he wrote for Sports Illustrated and The Big Lead. He enjoys expensive bourbon and cheap beer.


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  1. I’m very happy for Clayton Kershaw. This guy deserves recognition as the greatest pitcher of our generation. He’s the best since Pedro retired. Whether he won a World Series or not, the guys a HOFer. He’s a good man, good teammate, a true professional, a gamer, and I’m very happy to see guys like him rewarded after enduring so much criticism.

  2. Steve Young. Having to play with the stigma of never winning the big one as QB of the 49ers when Dallas was constantly going upside their heads, not to mention losing the head-to-head vs. Montana in KC in ’94 (and the 40-8 beatdown by the Eagles where he got pulled). He went on a tear after that and finally got the monkey off his back in SB XXIX (on my birthday too).

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