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If Theo Epstein trades Kris Bryant, how good a deal will he make?

If he has to trade Kris Bryant, how likely is the Chicago Cubs boss to make a good deal?

Even the thought that the Chicago Cubs might be open to trading star third baseman Kris Bryant has prompted discussion on a closely related topic: how good has Theo Epstein been at handling personnel questions, anyway?

On MLB Network’s High Heat Monday, Chris Russo was particularly critical of Epstein’s ability to handle free agent negotiations, something that would be critical in a few years if the Cubs decide not to move Bryant. He would be a free agent following the 2021 season, and he is represented by Scott Boras, who is notorious for taking his clients to free agency.

Indeed, Bryant was reported to have recently turned down a $200 million deal for an unspecified number of years, a gesture widely read as declaring his intent to leave the Cubs.

In his critique of Epstein, Russo noted the Chicago Cubs president’s pre-2016 signing of Jason Heyward to a $184 million deal along with his pre-2018 signings of free agent pitchers Yu Darvish and Tyler Chatwood, neither of whom panned out.

Assessing Epstein in that subjective manner has a certain emotional satisfaction, but it lacks the precision of a more objective approach. Such an approach requires rating his decisions during 16 seasons as a general manager in Boston and then president in Chicago. The best tool for such a measurement is Wins Above Average, a zero-based variant of Wins Above Replacement that measures a player’s value against the value of all major league players rather than against replacement-level talent.

GMs essentially have five duties: maximize the value of players acquired in deals with other teams, minimize the value of players lost in deals with other teams, maximize the value of players acquired via free agency, minimize the value of players lost via free agency, and maximize the value of rookie callups.

Since those values accrue both on a short-term and long-term basis – short-term referring to the value of deals made since the end of the previous season and long-term encompassing the value of deals made prior to the end of the previous —  that provides 10 points for analysis.

Here’s Epstein’s average per-season rating for the value of each of his five short-term ratings. The values are expressed in WAA – that is essentially games better or worse– per season:

  • Short-term trade value                 -0.34
  • Short-term free agent value       +0.65
  • Short-term farm system value   -0.55
  • Short-term trade loss value        +0.12
  • Short-term free agent loss          -0.19
  • Total                                                   -0.31

In sum, the average short-term impact on his team of all of Epstein’s moves is about -0.31 games per season. That sounds condemnatory – how can a GM succeed if his moves hurt his team? – but it’s not. The reality is that most personnel transactions have a negative short-term impact. In 2018, 16 of the 30 general managers produced a negative short-term rating, and that rating averaged about -2.5 games per team.

Front offices don’t succeed due to the impact of their short-term moves; they succeed over time due to the cumulative long-term impact of those moves. Here’s Epstein’s average per-season rating for the value of each of his five long-term ratings:

  • Long-term trade value                     +1.47
  • Long-term free agent value            +3.19
  • Long-term farm system value       +4.58
  • Long-term trade loss value            +1.63
  • Long-term free agent loss              +1.08
  • Total                                                   +11.95
Next: 5 Bryant trade destinations

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So the true key to gauging Epstein’s ability to improve a team – and this would be true of almost every front office leader – doesn’t lay in his short-term impact but rather in his usually much greater long-term impact. If he decides to trade Bryant, the worth of that trade won’t accurately be measured in what happens to the Chicago Cubs immediately, but in what happens to them over time.

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