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Clayton Kershaw on the Yankees? GM Brian Cashman Reveals He Tried to Acquire Dodgers Star
National League pitcher Clayton Kershaw of the Los Angeles Dodgers prior to the 2019 MLB Home Run Derby at Progressive Field on July 8, 2019. Charles LeClaire-Imagn Images

Yankees general manager Brian Cashman has been doing the job longer than any of his peers — since February 1998, to be exact. Given the sheer volume of major and minor league players active over the last 27 years, it's possible Cashman has attempted to trade for more players than any GM in baseball history.

One of them was Clayton Kershaw.

Cashman revealed his decades-long interest in Kershaw on MLB Network Radio on SiriusXM.

"I remember Ned Colletti, he was GM of the Dodgers when Clayton was in the minor leagues," Cashman said. "I threw some ideas his way to try to pilfer him, and of course Ned was smart enough to say no to it, but they were legitimate efforts on my part."

Kershaw wasn't a minor leaguer for long. Drafted in the first round (seventh overall) in 2006 by the Dodgers, he skipped straight from Double-A to Los Angeles two years later.

Along the way, there were enough bumpy starts in Kershaw's journey that Cashman thought to call Colletti with a genuine offer.

"Early on, he struggled," Cashman recalled. "That's where you get the vulnerability, especially in these big markets, where you need immediate dividends or the fan base gets a little bit pressure point about trying to win. You want to cough up something good. I'd love to hear how many offers came people's way trying to take (Kershaw), but the Dodgers were smart enough to say no, no no, no he's ours for life."

It's worth remembering where each franchise was when Cashman made his offer.

The Dodgers were a National League Wild Card team in 2006, and lost in a three-game sweep to the New York Mets. But the following year, they won only 82 games and would fire manager Grady Little after the season.

The Yankees were in an arguably tougher spot as a franchise. In 2007, they finished second in the American League East for the first time in a decade. In 2008, they would finish third and miss the postseason for the first time since 1994 — when there was no postseason.

Manager Joe Torre would coincidentally leave the Yankees for the Dodgers after the 2008 season. Colletti didn't even have to trade Kershaw to get him.

Many of the Yankees' best players during this stretch were over-30 veterans who would not have helped the Dodgers become perennial NL West champions in the decade to come. In 2008, Mariano Rivera turned 38. Andy Pettitte turned 36. Jason Giambi (37), Jorge Posada (37), Bobby Abreu (34) and Hideki Matsui (34) likely would have not enticed many GMs into trading their best pitching prospect.

The famous left side of the Yankees' infield — Derek Jeter (34) and Alex Rodriguez (32) — was unlikely to be traded at all, if they could even fit within the constraints of Frank McCourt's shrinking payroll. Robinson Cano (who turned 25 in 2008) and Brett Gardner (who turned 24) might have made for an intriguing centerpiece in a Kershaw trade, but it wasn't to be in either case.

The Dodgers kept Kershaw. The rest is history.

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This article first appeared on Los Angeles Dodgers on SI and was syndicated with permission.

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