He's been here for 2 offseasons and found one each offseason. I'd say just looking at his Cubs track record alone says yes and expanding it to the Boston track record only helps. This has as much to do with other GMs as it does Theo, but I tend to think it's pretty likely that Theo will be able to. There was too much smoke last offseason to think there's simply no interest in Soriano out there, it's just whether the offers match our demands. That's somewhat a question only Theo can answer, but I'd guess there will be more urgency to deal him this year. This is 100% on Ricketts. If he allows the money to be spent and Theo values Choo enough, yes. If Ricketts doesn't make the cash available, no. Unless Choo has non-monetary motivations, if the Cubs (read, Ricketts) want him bad enough, then we can outbid other teams for him. Probably, but I trust Theo enough to believe he can manipulate the roster enough to get a few guys who can outperform their norms for a season. I question whether the totality of Tim's scenario would play out that way, but each individual aspect of it isn't particularly far-fetched. The thing I'm worried about the most, probably, is getting everything to work together to net Choo.