My first reaction upon hearing that Theo Epstein was stepping down from his role with the Cubs was to wonder if there’s a way to get him in the Bronx. You know, get Cashman to do something inappropriate on a Zoom call perhaps, a la Jeffrey Toobin?
No, seriously.
Even if I were kidding, I was glad to see that Epstein wants a role in MLB addressing its aesthetics and future growth. As someone who loves data and statistics, I agree with Epstein 100% that the data and analyses that we know lead to individual and team success isn’t always the most fan friendly or aesthetically pleasing approach. I’m glad someone with his resume and perspective wants to address such issues, as opposed to another crotchety coot dusted off and granted a figurehead role with MLB.
(Pssst…Theo…I know I’m just a barely professional writer, but if it were me, losing the infield fly rule and shrinking the strike zone would be numbers 1 and 1A on my “Improve the Game” agenda.)
With much discussion about Theo’s legacy and track record out there, I wondered exactly how much impact his decisions had on the Cubs’ success, particularly the 2016 World Series win, during his tenure. This may seem odd to you that I’d wonder, but experience has taught me to be skeptical about the impact front office and field management personnel have on team success. Quite often, good timing and good luck have as much, if not more to do with a team’s good fortunes than leadership’s decisions. (See; LaRussa, Tony).
So I did a little digging, and here’s the Cliffs Notes version of Theo’s north side tenure:
2011: Hired after the season, inherits a team with a $136 million payroll that won 71 games.
2012: Hires Jed Hoyer (GM) and Dale Sveum (field manager), cuts payroll to $86 million. Team wins 61 games but does add Anthony Rizzo in a heist of a trade.
2013: Drops payroll to $67 million, team wins 66 games.
2014: Replaces Sveum with Rick Renteria, cuts payroll to $59 million, wins 73 games. Added Jake Arrieta and Kyle Hendricks and gave up (checks notes…) nothing for them.
2015: Almost doubles payroll to $115 million, hires Joe Maddon to replace Renteria, adds Dexter Fowler and Jon Lester as free agents and former 1st round pick Kris Bryant joins the team – the team wins 97 games.
2016: Bumps payroll to $176 million, adds John Lackey and Ben Zobrist as free agents and trades for Aroldis Chapman. Teams wins 103 and the World Series.
2017 – 2020: Team averaged $195 million in payroll, 91 wins (using per 162 prorate for 2020 numbers) and made the postseason 3 of 4 seasons. Also, added Yu Darvish as a free agent and traded for Cole Hamels for nobody who’ll be missed and got a very good season and a half from him.
Overall: Rids team of crap contracts, gets Rizzo, Arrieta, and Hendricks in trades for nothing, signs Fowler, Lester, Lackey and Zobrist as free agents and adds Bryant through the draft – all of whom had a major impact on the 2016 title. Four years later, he leaves his successor with a roster with multiple stars in their prime.
Holy Commissioner’s Trophy kissing Christ…
But there have to be blemishes, right? Of course, nobody bats 1.000, but…
“The draft record isn’t that good. Bryant is the only Epstein pick to work out and everyone knew he was going to be a stud (well, except the Astros, who took Mark Appel ahead of Bryant)”, some folks might say. I considered this. Then I checked Brian Cashman’s draft record…and LOLed.
“$184 million for Jason Heyward? He’s the Cubs’ answer to Chris Davis!”, other folks might say. Heyward was coming off a 6.9 WAR season, with a 6 year average of 5.0 WAR per season, and was only 26 years old. For context, Manny Machado was coming off an almost identical stretch of production at the same age but was coming off of a down season for him – he got $300 million. No way the Heyward signing can be criticized.
Sometimes it’s luck and timing and a mainstream media that’s too lazy to think things through that create success in MLB. Not in Theo’s case. He’s going to be in Cooperstown one day, deservedly so.
Did I miss something? Let me know.

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