Tyler Chatwood- Cubs
This one doesn’t make a lot of sense at first glance, but hear me out and I may be able to convince you that it’s at least possible.
The Cubs signed Tyler Chatwood to a three year, 38 million dollar deal before the 2018 season, and so far it’s been a bit of a disaster. Chatwood posted a 5.30 ERA and a 1.804 WHIP in 20 starts and 24 total appearances, and eventually lost his spot in the rotation after the Cubs gave him plenty of opportunity to get things turned around.
With 25.5 million remaining on the two years left on his contract, Chatwood’s commitment is quite a bit cheaper than what the Blue Jays owe Troy Tulowitzki, so it wouldn’t be a one for one swap in this case. The Blue Jays could eat some money in order to get a deal done, or they could also include some prospect value, or possibly even a reliever from the big league roster. The Cubs showed that they could use some help in that department this season, and especially in their Wild Card game against Colorado, so perhaps someone including someone like Ryan Tepera would get it done, although the Blue Jays may want to explore his trade value elsewhere too.
The Cubs are also expected to let Addison Russell go after he was suspended for 40 games due to allegations of domestic violence. They have the luxury of sliding Javier Baez over to shortstop and using a variety of players at second, but they could find a way to fit Tulowitzki into their creative infield picture, if he was healthy of course. Tulo wouldn’t be guaranteed playing time there, or a set position, but almost no one in Chicago is afforded that luxury.
Realistically, this probably isn’t going to happen, mostly because the Cubs will likely seek to improve their offence this winter with any additions they make. While Tulowitzki could theoretically add some depth to their lineup, it’s pretty hard to count on him to stay healthy enough to do anything these days. It would rid the Cubbies of Chatwood’s contract though, and a pitcher who it looks like they have very little plans for anyway. You never know.