I imagine they are always looking for bargains, and monitor multiple dozens of guys of interest, in hopes that their price might unexpectedly fall from "that's too much" into "good value" realm. I'm sure it rarely happens, but I think by Cubs account it has happened in a couple of significant occasions.
One was the great Heyward steal, Theo and Maddon had loved the guy, but didn't think they could afford him. But then it turned out there was a chance, and their age-based analytics scouted his best-hitting years were coming up, that there was more power to be gained from the Cubs coaching and launch-angle analysis, and they got him for the $184, and the rest is history.
In both the Hewyard year, and the Tanaka year, Theo has talked about having spending flexibility. I think Hendry tended to get one-year budgets, and he normally felt it was his obligation to the fans to spend out his budget to try to assemble the most competitive team he could. But Theo I think has more flexibility. He talked about with the Heyward pickup, where he thought the value was too good to pass up, that he was allowed to kind of "borrow forward", and borrow money from the next year; and he got authorization from Crane Kennedy to pay beyond what the suggested budget had really authorized. I assume some of that flexibility remains in play now, such that *IF* a really-good-value pickup became available, they could possible "borrow forward" again.
I suspect Yu may have been another case. The word had been that their budget was limited, and that they were kind of saving for this year that was supposed to have a bigger field. But then I think Yu with his World Series collapse and the pitch-tipping and everything, his market wasn't as strong as deeg had expected, or maybe Theo either. So, by Theo's account, when Yu got slightly more affordable then they expected, and given their pitching-rotation needs, they somehow got the flexibilty to take the plunge last year. AGain, I suspect they were partly "borrowing forward", and trying to take their best shot before their window kept slimming. Plus, I assume they are always doing some revenue-guessing; the revenue for a team that plays into the world series and has a bundle of extra home games is significantly larger than for the one-game playoffs that the Cubs hosted. So the revenue may have been some handfuls of millions less than they had projected?
But, I would assume that **IF** a price drops low enough, that Theo may again be able to make a case to borrow forward, and that the window is going to shrink and they should take their shots while they can?