MLB: Chicago Cubs-Workouts

Epstein Finds Advantage in Honesty

Ever since the release of Moneyball, one of the most popular buzzwords in major league baseball has been “market inefficiency.” For over a decade, fans and analysts have been captivated by the endless quest to identify teambuilding trends that everyone else in MLB is missing. Unfortunately, for most of that time, the Cubs lagged behind the rest of baseball in that area. This is evidenced by the priorities of the Cubs front office during a random sample of seasons from the past decade:

2005: Players who remember that a baseball game lasts nine innings

2006: Players who show A.J. Pierzynski the definition of karma

2009: Sociopaths

2011: Managers without eyebrows

Thankfully, under the current regime, things have changed, and the Cubs have caught up to the rest of baseball in their search for hidden assets within the game. And with Theo Epstein as team president, it appears that the Cubs have the market cornered on an undervalued commodity in major league front offices: honesty.

As Rian Watt has previously pointed out, listening to Theo Epstein speak is an exercise in appreciating an executive who means everything he says. But the benefits of Theo’s honesty go beyond addressing his fanbase like they aren’t currently wearing shirts that read “Drunk chicks dig me.” When viewed within the context of Epstein building relationships with his players, that honesty also returns real benefits to the team.

From his first year with the team, Epstein made it clear that he was going to deal with his players in an upfront manner. Oddly enough, this came to prominence first during the Great Ryan Dempster Trade Deadline Drama of 2012. Epstein’s forthrightness was called into question early on in the saga when Dempster blocked a trade to the Braves, presumably because he couldn’t scream “SWUNG, BELTED” on a routine fly to center loudly enough to nail a proper Chip Caray impression. At the time, Dempster was under the impression that Epstein had assured him that he would end up in his preferred destination of Los Angeles, and became upset that Theo had seemingly reneged on this pledge.

Less than a full season into his tenure, Epstein’s reputation and integrity were already being tested. So he took the unprecedented step of letting Dempster into the Cubs’ offices so he could hear firsthand that a trade with the Dodgers was not happening. And after seeing clear incontrovertible evidence that he wasn’t being lied to, Dempster eventually approved a trade to Texas. This was an extreme case, but it demonstrated the lengths to which Epstein would go to be transparent with his players. And because Epstein went this far to prove that he was being upfront with Dempster, a couple of good things happened:

1. A trade went through that brought Kyle Hendricks to the Cubs.

2. After retiring, Dempster returned to the Cubs as a special assistant to Epstein.

(Where, presumably at least once a day, Theo calls him into his office to listen as he asks Andrew Friedman, “What do you say to Dempster for Kershaw and Seager?…When hell freezes over?…Good news, Ryan! I can trade you to the Dodgers after we win a World Series!”)

The latter result gets to the heart of why Theo’s philosophy is an advantage for the Cubs (besides, you know, honesty being an inherently good thing). Epstein’s policy of honesty and transparency helps to build trusting and adult relationships with important players.  And those players remember being treated in a professional and upfront manner when they have to make decisions about their futures.

This benefited the present day Cubs in a huge way with the surprise Dexter Fowler reunion. One of the first things Fowler told the media upon returning to the team in February was “I feel like the Cubs treated me with the utmost respect.” When Fowler felt that the Orioles did him wrong, his history of forthright dealings with Epstein came into play and ended up paying off for the Cubs. After dealing with Peter Angelos, it was an easy decision for Fowler to re-sign with the executive who treated him like an adult.

And Fowler is far from the only current Cub who has build a fair and honest relationship with his boss. Epstein’s honesty also proved crucial to building a relationship with Anthony Rizzo. Back when they were both with the Red Sox, Epstein had to trade away his prized first base prospect in order to land Adrian Gonzalez. After doing so, Theo made it a point to let Rizzo know how highly he was valued:

“I did tell him, ‘Hey, we’re going to try to get you back’… I told him we’d be on the same side again at some point, just because… I believed in everything about him. We had a special connection, and he was still a young man. I felt like our paths would cross again. It was fun, when we traded for him with the Cubs, to remind him of that over the phone. He was like, ‘Oh, I remember.’”

When Epstein followed through on his promise to reunite with Rizzo, it reinforced that all the good things he said about him as a player came from a genuine place. And this was helpful later on when Rizzo had established himself and Epstein approached him about a long term deal. As Benjamin Franklin said, “Honesty is the best policy. Especially when you’re not lying about paying me $41 million.”

Honesty is also an essential part of Epstein’s technique for recruiting free agents. To get a sense of this, consider Epstein’s longstanding professional relationship with Jon Lester. When discussing what brought him to the Cubs, Lester identified an intriguing tell that convinced him that he could trust Theo during his recruiting pitch.

“I knew when he was kind of BSing me, I knew when he was telling the truth, and it didn’t take much for him to convince me about these young guys…The biggest thing that sold me was just how arrogant he was about it — and I mean that in a good way, just how confident he was in these guys because these guys were not going to be failures.”

It appears that Epstein is one of the few people in the world whose pomposity is directly proportional to his correctness. This is why he’s been such a success as a baseball executive and why he would be an utter failure as a baseball blog commenter.

But further information about this meeting revealed that more than just arrogant honesty helped to land Lester. And these details showed that Epstein had established such a close relationship with his ace pitcher that the level of Theo’s honesty in that meeting reached the point of calling his shot.

“As part of the elaborate presentation during Jon Lester’s recruiting visit to Wrigleyville, the Cubs unveiled a diamond diagram projecting their 2016 lineup – with Jason Heyward playing center field… They kind of broke down their ultimate plan,’ Lester said. ‘(Heyward) was kind of their big guy they pitched to me.’”

And in an especially eerie touch, at the bottom of the diagram was written “On December 15, 2015, the number one trending topic in St. Louis will be #Trader.”

According to Patrick Mooney, Epstein was blunt in telling Lester his expectations for 2015 were for him “to front their rotation, account for 200-plus innings and help a young team play meaningful baseball in September and maybe win around 84 games.” Knowing that this wouldn’t be the most inspiring pitch for the free agent starter, Epstein went the extra mile and revealed details of the big picture he eventually had in mind.

This meeting was more than just a simple recruiting pitch to Lester. Epstein was establishing a level of trust between the two of them deep enough to share the specifics of his plans for building a foundation for sustained contention in Chicago. And it could only have worked if Theo had earned Lester’s trust through honest communication over the many years of their professional relationship.

Major League Baseball is an extremely harsh business and players learn quickly to distrust management. But Theo Epstein stands out from a rather motley crew of executives by means of his reputation for straight shooting with his players. And this ends up making the Chicago that much more of an attractive destination and a place where players want to stay. In a business full of sycophants and snake oil salesmen, Epstein is Bizarro Loria. And it’s one of the reasons why his teams have the one quality Loria’s home run sculpture will never have: watchability.

Lead photo courtesy Rick Scuteri—USA Today Sports.

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1 comment on “Epstein Finds Advantage in Honesty”


I would not argue with your basic premise here, but Theo has definitely benefited from running two teams that have given him the financial resources to execute his plan.
When you think about it, his building of the team pre-2015 was pretty shrewd and could have been done in any market, but the remaining pieces (Lester, Heyward and Zobrist) would have been difficult to sign in other places.

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