Given the nature of the executive role in baseball, you’d just about always like to have your guy in charge with a few years left on his deal. Why? The top executives – president, GM, whoever – are in control of building the roster *and* managing the long-term health of the organization. Sometimes, one of those things (the latter) can be compromised unnecessarily to the benefit of the other thing (the former). To reduce the incentive to do such things, you’d like to be in a situation where the guy in charge doesn’t persistently feel like he’s got to win RIGHT NOW, future be damned.
To be sure, I’m not really concerned about Chicago Cubs President of Baseball Operations Theo Epstein being the kind of guy who short-circuits the long-term meal for a short-term dessert, and I’m also not concerned that Owner and Chairman Tom Ricketts doesn’t appreciate what Epstein is accomplishing for the Cubs. But, as Epstein heads into the fourth year of his five year contract with the Cubs, I do think it would be appropriate to formally marry up for several more years. The Plan is proceeding well, and no one wants any possible threat of continuity disruption to alter the course.
Business president Crane Kenney has already been extended through 2019, and it would be swell to sync up – eh hem – the baseball and business sides in yet another way. So, is an Epstein extension coming?
You can read Epstein’s thoughts on that subject here at CSN and at the Sun-Times. The short version is that Epstein isn’t focused on getting an extension, at least not publicly, though he does suggest those kinds of discussions could take place this offseason. He did drop the excellent “when it happens” line, which is something of an anthem among Cubs minor leaguers (i.e., when it happens, where will you be?).
All in all, there isn’t a spectacular rush to get an extension in place, given that I don’t have any concerns about Epstein making rash decisions in fear of his job security. If things keep proceeding as they are, and if Epstein wants to stay, he’ll stay. There are likely numbers to be negotiated, obviously, but, eventually, I’m assuming something will get done.