Theo Epstein Wooed Jon Lester With Fictional Video Of Cubs Winning World Series

By Michael Hurley, CBS Boston

BOSTON (CBS) — Two years ago, Jon Lester found himself to be a very sought-after man.

He was about to turn 31 years old. He was in the prime of his career. He was a left-handed starting pitcher who was a lock to throw 200-plus innings every year.

He essentially could have signed with any team he wanted, and he could have named his own price.

And with the baseball world at his fingertips, Lester opted for a reunion with Theo Epstein by signing with the Chicago Cubs.

The reasons were many, starting with the $155 million over six years. But in a new profile of Epstein on, the curtain has been peeled back a bit regarding how Epstein got the prized free agent to join the Cubs.

“He obsesses over details,” wrote Wright Thompson, “from the draft board to the recruiting video he made while wooing Jon Lester, complete with a fake World Series call by the real Cubs announcers.”

For Epstein’s sake, one has to hope that the video has since been destroyed. If the Cubs end up winning more than 100 games but fall short of their goal of winning their first World Series since 1908, that video might drive some Cubs fans to the brink of their sanity.

Obviously, Lester wouldn’t have been the first player to sign with the Cubs in hopes of ending that long and painful championship drought, but we now know the extents to which Epstein worked to exploit that desire.

It’s a feeling that, based on the profile, Epstein has himself despite already ending the “curse” in Boston.

“He longs for that again, and a title in Chicago would combine the best of 2004 and 2007,” Thompson wrote. “He’s after a feeling, even if he knows better than most how quickly it goes away, and how hard it is to find once it’s gone.”

The story also delves into Epstein’s departure from the Red Sox — a move that was precipitated by a “cold war” between the baseball operations department and the powers that be in ownership.

“It’s rare you can find true togetherness, selflessness, connectedness,” Epstein told Thompson. “We had that in baseball ops. It was in opposition to what I saw going on in the rest of the company.”

Accusations in the story include the ownership group “plant[ing] stories in the paper to minimize blame for trades and who worried more about public perception than the long-term health of the franchise.” Additionally, Epstein said he was told that based on data collected by focus group research, he would have to pursue big-name free agents, even if the team didn’t necessarily need them, based on the desire to boost television ratings.

The story also included Epstein’s “pranks,” which sometimes brought about some very real — and very unpleasant consequences. He apparently put laxatives in some hummus during spring training in 2004, sending someone to the bathroom for an unexpected visit or two. And he also once tried to let off some steam by teeing up a golf ball and driving it down a narrow hallway. The ball — unsurprisingly — ricocheted off some walls and ended up catching Ben Cherington right in the forehead, drawing blood.

Theo’s “pranks” don’t sound very fun. But the story is fascinating and worth the read.


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