If you're really wanting to see us bring Jackson in, one thing you have to be concerned about is that Theo so far has been pretty consistently coming in 2nd or 3rd place on these free agents who want multi-year contracts. So far, there's been a reluctance to go all the way on guys like Anibal Sanchez, Jeff Keppinger, Jason Grilli, Mike Adams, etc.
Granted I have no real problem with that, since we're at a point in the rebuilding process where we don't need to be doing a lot of that. Still, if you want free agents, you have to overpay to bring them in, especially in our situation. We obviously didn't want Sanchez badly enough where we were willing to give him a 6th year or pay him $17-18 million per year to make sure we got him in.
So does Theo really want Jackson badly enough to outbid the Rangers for him? The Rangers are in win now mode, have a ton of money to spend, and a clear need for a pitcher like Jackson. Just based on where the Rangers are and Theo's reluctance to pay any price for most of our higher end free agent targets, it doesn't seem especially likely.