Clayton Kershaw Almost Joined Yankees Before Dodgers, Brian Cashman Reveals in Insane Confession

He was hoping to catch the Dodgers at a moment of weakness. “I think early on he struggled if I remember right,” Cashman said. He saw a small window of opportunity. “And so that’s where you get the vulnerability… where you need immediate dividends or the fan base gets a little bit, you know, pressure point… and you wind up coughing up something good.”

But the Dodgers and their GM, Ned Colletti, never blinked, as they knew exactly what they had in the future superstar. As Cashman put it, “the Dodgers were smart enough to say, ‘No, no, no, no, no, he’s ours for life.’ And they obviously drafted, developed, and kept a great one.”

Though it never happened, Cashman’s confession reopened the great “what if” file, inviting a deeper look.

The rotation that could have been

To understand the gravity of that moment, you have to look back at around 2008. The Yankees were an aging empire desperate for another title. Their rotation featured a 40-year-old Mike Mussina and a 36-year-old Andy Pettitte. They were definitely big names, but surrounded by inconsistent arms like Chien-Ming Wang and Sidney Ponson. Young arms like Phil Hughes, Joba Chamberlain, and Ian Kennedy promised upside but carried risk. This is why Cashman pursued such an offer.

While we don’t know the exact offer, we can take a guess, right! A serious deal for Kershaw would have started with two of the top pitching prospects like Phil Hughes, Ian Kennedy, or Joba Chamberlain from the Yankees’ farm system, considering it would have been massive. Cashman could even include a top outfield prospect named Austin Jackson in that deal.

And Colletti’s ‘no’ sent both franchises down wildly different paths.

Imagine if Kershaw had become a Yankee. He would have joined their rotation in 2008 and been a key piece of their 2009 World Series championship team. The  Yankees signed A.J. Burnett before their 2009 World Series win. So the curiosity remains: Would they still feel the need to commit $82.5 million to Burnett if they already had an ace in Kershaw? And it is a near certainty that the Yankees, with their financial might, would have matched or exceeded the then-record seven-year, $215 million contract extension Kershaw signed with the Dodgers.

And for the Dodgers, their string of NL West titles from 2013 through 2019 might easily have ended much earlier without Kershaw. As we all know, from 2009 to 2015, Kershaw was arguably the most dominant pitcher on the planet, winning three Cy Young Awards and an MVP.

So, the story now joins the pantheon of baseball’s greatest “what-if” scenarios with Barry Bonds almost becoming a Yankee in 1992, or when the Yankees nearly traded a young Mariano Rivera in 1996.