Clayton Kershaw has been a member of the Los Angeles Dodgers since 2008 and despite establishing himself as one of the greatest pitchers of all time, he only added a World Series ring to his accomplishments in 2020.

The Dodgers had plenty of championship opportunities before that, as they won the National League West Division title in 2008-09 and then eight straight from 2013-19. However, the team n failed to get the job done in each of those seasons, and sometimes she felt like she never would after each heartbreaking loss.

Kershaw has often been singled out for the Dodgers’ struggles. His career playoff ERA is nearly two points above his regular-season mark and he was on the mound multiple times when the Dodgers suffered some of their most memorable slumps in October.

Although it cost him dearly, Kershaw said he would have rather continued to make the playoffs and failed than miss it altogether; and previous failures ultimately made winning the World Series even more special for him, via the “Dan Patrick Show”:

“I’ll say it 1,000 times: I would much rather continue to be successful and fail over and over again, but continue to get there. Because that’s what you play for. You want to be there, and failure is part of athletics. It’s part of the sport. I think that’s a great lesson. I learned a lot of things by failing as many times as I did.

“Obviously, I don’t recommend it. If you can just win it, you should win it. But when I finally did it, it was pretty special. Ultimately, when you’re on the Dodgers and making the playoffs every year, the World Series is your expectation.

Now, Kershaw has reached free agency for the first time in his career. He has nothing left to prove after finally winning that elusive World Series, so he could choose to retire, but it seems likely he will keep playing.

Teams tied to Kershaw have been the Dodgers and his hometown Texas Rangers. That leaves it up to him to decide if he wants to retire with the Dodgers and compete for a ringside every season or play at a stadium near his home and help make the Rangers real contenders.

Kershaw’s comments sound like he’ll want to re-sign and compete with the Dodgers every year, but the chance to return home can be a strong incentive for anyone.

Kershaw named one of ESPN’s Top 100 MLB Players of All Time

Kershaw was ranked 52nd on ESPN’s list of the 100 Greatest MLB Players of All Time, after fellow Dodgers legends Sandy Koufax (#32) and Jackie Robinson (#38) and ahead of Roy Campanella (#83 ) and Duke Snider (#95).

The 2020 World Series champion was an eight-time All-Star and won five ERA titles, three Cy Youngs, the triple pitching crown, a gold glove and the 2014 MVP award.

Are you subscribed to the Dodger Blue YouTube channel? Be sure to ring the notification bell to watch player interviews, participate in shows and giveaways, and stay up to date with all the Dodgers news and rumors!