Chet Coppock's Fur Coat wrote:
Theo's strength in Boston was that he was able to rebuild with veterans because he had ownership which was willing to buy expiring contracts and collect compensatory draft picks. With a bunch of those draft picks, they managed to keep restocking the minors with high end draft talent like Pedroia.
Theo gets to Chicago, and a year later the owners changes the rules and require a Qualifying Offer to get draft picks. So part of the spinning through the dregs of 2011-2013 was adjusting to those changes. They got some prospects like Russell and Montgomery by dealing veterans and organizational soldiers, but the volume wasn't there.
So you get to 2017, and other than Happ there really aren't any drafted bullets left in the chamber, and they panic and trade Eloy because they see a logjam in LF and they don't feel that they have any other pieces to get pitching. And after Ricketts saw the 2017 melt down, he balked at the need to purchase talent at market prices.
Fast forward, and I just don't think either Theo or Ricketts sees any hope short of another teardown rebuild right in front of a likely work stoppage. I don't think there's animosity, it's just reality.
Theo's REAL strength in Boston was unlimited spending on draft picks. Great talents who were otherwise unsignable for any number of reasons for less financially capable teams would fall in the draft to the Red Sox, who didn't have the same budgetary constraints.
Think of it, if top five talents of every draft fell to a team at 30 every year. Not only that, top talents (acknowledged as such by everyone, including the teams passing on them) were falling down to them in later rounds as well. It didn't take genius to pick these guys. It took convincing an owner it was cheaper to spend for a high priced draft pick (probably less than the MLB minimum) than an MLB free agent.
It was actually JR who put a stop to this as he was never going to be a guy who opened the pocketbook.
Suddenly, Theo no longer had his advantage and had to resort to signing incredibly high priced MLB level free agents. Many of these players underperformed and the rest is really history in Boston.
Now, Chicago, Theo's answer to this was to tank for a handful of years so that he still had those top 5 picks, but the traditional route. When he didn't pick high, he was no longer a genius.
The truth of his Cubs tenure though is that if Arrietta didn't suddenly gain the body of a greek god when he got to the Cubs, the Cubs are barely a playoff team. There were a few middle of the road veterans who magically became HOF level players under Theo's watch in both places. I guess he was just really good at finding them