More on the Theo Epstein Deal: Compensation, Other Extensions, Ricketts

theo epstein and tom ricketts

There are plenty of things left to accomplish this season – in fact, aside from winning the NL Central, nearly all of the remaining hurdles are the most important.

But one such hurdle was cleared yesterday afternoon, and we almost caught off guard.

Of course, I’m referencing the long-awaited extension for President of Baseball Operations Theo Epstein, whose original deal with the Cubs was set to expire after this season. Moreover, we got word that General Manager Jed Hoyer and Senior Vice President of Amateur Scouting and Player Development Jason McLeod would also be extended.

While we came to expect that an extension for Epstein and Hoyer would eventually get done, we never got much more than “Don’t worry about it …”, which is fine in April, but a bit more nerve-wracking near the end of September. Similarly, not one week ago, McLeod appeared to be just days away from becoming the President or GM of entirely different ball club; today, we know he could still be with the Cubs for a long time. [adinserter block=”1″]

The extensions have been written about many times over, so let’s wrap up some of the details with a bullet-style piece. Some articles for your perusing are at Cubs.com (Muskat), ESPN Chicago (Rogers), the Chicago Tribune (Gonzales), CSN Chicago (Mooney), CBS Chicago (Levine), Today’s Knuckleball (Heyman), BP Wrigleyville (Watt) and Yahoo Sports (Passan).

  • On those suggestions “not to worry,” however, I think they (Tom Ricketts and Theo Epstein) were justified. Apparently, back in Spring Training the two met for dinner in Arizona where they began discussing a contract extension. Ricketts told Epstein that he was the best in the game at what he did, and Epstein told Ricketts he wasn’t going to leave Chicago “no matter what” Ricketts paid him. Suddenly, I understand why they weren’t as worried as we all were. Apparently they met a few more times in-season, to finalize some details, but it doesn’t seem to have been a contentious negotiation.
  • But don’t let Epstein play the pauper, because he is reportedly getting paaaaaaaid. The final financial figures haven’t been officially reported, but Jon Heyman (Today’s Knuckleball) is suggesting the new deal will pay Epstein “a bit less than $50 million” over five years, but has other incentives that could take him over that mark. Epstein’s last deal (5 years/$18.5 million) was one of the largest in baseball at the time. This would shatter that figure.
  • The current record, for what it’s worth, is held by the Los Angeles Dodgers’ Andrew Friedman who is thought to make somewhere between $7-8 million annually. If the reports of Epstein’s deal are true, his will likely fall in the $9-10 million range – making him the highest paid executive in baseball. But that’s been the Cubs way since Ricketts has taken over. The right people are the right people. Cost needs to be considered, of course, but the future health of the organization trumps everything. The Cubs are best off with Epstein at the helm.
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  • Similarly, the extensions for Epstein’s right and left hand, Jed Hoyer and Jason McLeod, haven’t yet been announced, but are apparently in the process of being finalized. As soon as details surrounding their contracts get out, we’ll let you know. Even still, I don’t want to downplay the importance of their extensions with the Cubs. Remember, all three executives are among the most sought after front office personnel in baseball. Each is more than capable of (and has been asked to) running organizations of their own (in fact, McLeod had just recently interviewed for the vacancy at the very top of the Twins front office). So the fact that the Cubs have three of them in one front office is like having three aces in your rotation.
  • The early reports do suggest that all three extensions will be for a total of five years (McLeod had two years remaining, but tacked three on to the end), taking the triumvirate through the 2021 season. Anthony Rizzo, Kris Bryant, and Addison Russell’s team control runs through the 2021 season as well – how about ten year extensions for everyone, instead?
  • Epstein, for what it’s worth, is very honored to receive such an enormous contract, and even sees it as a show of faith/validation from the Ricketts family for all of his hard work. He’s not one to take all of the credit, however. “The contract is really a product of all the hard work that literally hundreds of people have performed to make this a healthier and better baseball operation, from Jed and Jason and Randy (Bush) and Shiraz (Rehman) and Scott (Harris) to all the guys in scouting and player development and the R&D team, the guys behind the scenes.”
  • Similarly, Ricketts couldn’t be happier. “In the five years under Theo’s leadership, he has brought in a strong executive team and acquired and developed some of the best players in the game,” Ricketts said in a statement. “Now, the results are on the field. My family and I have no doubt that we have moved closer to our goal of delivering Cubs fans the World Series championship they deserve.”
  • Like I said, the remaining hurdles (NLDS, NLCS, and that gosh-darn World Series) are the most important and most difficult ones the Cubs have left to clear. But now, with Epstein, Hoyer, and McLeod sticking together, they’re in as good of a position as they could be.
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    written by

    Michael Cerami began covering the Chicago Cubs for Bleacher Nation as a part-time contributor in 2015. One year later, he joined Bleacher Nation full-time, covering the Chicago Cubs and Major League Baseball. Today, Michael runs Bleacher Nation, contributing as a writer (Cubs, MLB) and an editor for all sections of the site, including the Chicago Bears, Bulls, and Blackhawks, as well as MLB, NBA, NHL, and NFL. In 2019, Michael was the co-host of NBC Sports Chicago's Cubs Post-Game Show Outside the Ivy. You can find him on Twitter/X @Michael_Cerami

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