Seems to me like Theo is trying to bolt this offseason. I don’t blame him...if the Cubs were in a clear contention window that just needs a few changes he’d likely stay but by staying here for this team he would likely be kicking off a rebuilding/retooling process a year before he hands it off to another person. If that person is Jed, I guess it makes a lot more sense for him to stay. Either way, if Theo leaves this offseason he’s leaving the team in a really shitty position honesty. The farm is considered mediocre by the most optimistic people, the core is broken and have the lowest value in their careers, the owners are trying to slash payroll and there’s still considerable long term contracts on the books. Theo will leave an interesting legacy in Chicago. There is no question he will be celebrated rightfully for building that World Championship team and by far the most successful run of Cubs baseball since maybe the 30s or possibly ever. He is an unquestioned all time legend for this. But there are questionable contracts given out that fared poorly, trades that were made that seemingly gave up too much value (though almost all were justifiable at the time of trade and some directly impacted the world championship). And the decision to sit on this offensive core that he deemed broken exactly 2 years ago is so confusing to me, though clearly we don’t know what went on behind the scenes. But the biggest issue I’ve had is the inability to develop talent, particularly after 2016. He’s done a good job with 1st rounders and International FAs but he’s developed almost nothing at all in the draft beyond the 1st round. Here are all the players that Theo has drafted after the 1st round that have had a positive WAR with the Cubs: 2012 - Underwood (2nd, 0.1 WAR) 2012 - Bote (6th, 3.4) 2013 - Zastryzny (2nd, 0.2) That’s it...that’s the list. Now I acknowledge that I’m placing this all on Theo when there were many people involved with building the Cubs developmental system, some who likely had more impact than Theo, but as the VP of Baseball Ops ultimately he receives blame for this. If we were able to develop more talent in the past few years, there would be less concern about the payroll being capped and less need to stick with the current offensive core. The Cubs depth was greatly celebrated in 2015-2017 but was a glaring issue the last 2 seasons. Im not saying the Cubs should have been developing superstars to replace Schwarber and Bryant from mid-round picks but I think almost every team gets contributions from players drafted beyond the 1st round. I’d love to hear push back on these thoughts as I’d really like to appreciate Theo’s entire tenure rather than the first 5 years. No doubt he did some good things in the later years. Yu turned out to be a great signing and much needed this year. His ability to build a bullpen from scraps amazed me every year. He managed to keep the team competitive despite other issues which is recognized and appreciated. But can’t help but feel at least a small amount of disappointment for how things have gone the past 2-3 years.