Valid point about the contract, I always forget about that. I think if the Cubs finish around .500 and the farm system is still considered top 3-5 in baseball he'll be safe from heat. I'm not trying by cynical and suggest that Tom doesn't care about winning at all. He does, but I think whats most important to him from a baseball perspective is building a team that can develop players regularly to keep them from having to go into the luxury tax very often. (I mean to be realistic thats what almost every owner wants). Jed can still sell Tom on that vision even if the Cubs only win 78 games this year.
- .500ish team baseline (in this hypothetical)
- Top 5 farm system with many top guys in the upper minors
- Under the luxury tax, so no concerns about paying repeater penalties in short term
- Completely swagging it but something like $66m coming off the books from Hendricks, Bellinger, Smyly, Gomes, Bote, Neris and not a ton of arbitration raises I don't think (Steele is probably the only one that will be a significant raise)
There are absolutely concerns and if I'm right and he's not on the hot seat, negotiations on an extension will be interesting. But I would guess Tom is pleased with the health of the organization overall, he's making money, he can sell the fans (and himself) on the dream of a sustainable winner. Unless has an in house option he really likes, Tom doesn't seem like the kind of guy that is going to overhaul the organization when its doing a good job developing pitching and seemingly doing a decent job of developing hitting. Ripping it apart with a new regime before really seeing if many of the guys the current FO has spent the last 4ish years trying to develop could be seen as too rash for Tom.
I could be way off though. And of course I'm saying this from Tom's perspective, not my own. I have my own thoughts about the direction things are going but I have no say in it.