Yankees and Red Sox
Let me start by saying I don’t see this as a likelihood, at all. That said, I think it’s something to be explored from both sides, and the Yankees in particular make a lot of sense for the Blue Jays as trade partners, if not for that whole being in the same division thing.
For the Yankees the need is similar to most teams in baseball, as they could use an upgrade to their starting rotation. They have Luis Severino, but beyond that there are a lot of question marks. Masahiro Tanaka can be an asset most of the time, but he’s currently sporting a 4.58 ERA despite being 7-2. He’s also dealing with two strained hamstrings at the moment from running the bases, but that should heal soon enough.
The bigger problem is Jordan Montgomery has been lost for the year to Tommy John surgery, and Sonny Gray is struggling again. C.C. Sabathia has been good this season, but it’s hard to say how much he can be counted on as the season wears on. They could really use another starting pitcher, and maybe even two. The Blue Jays could definitely provide that with Happ, and even Estrada could have some value to them in the right situation.
There really isn’t a great fit for the Red Sox and Blue Jays to connect in a trade, unless the Red Sox decided to swing for the fences and bring in Donaldson. I don’t expect that to happen, especially because they’d be sending young assets to a team with a strong minor league system already, and that’s not a great recipe for their future.
I wouldn’t rule out the two teams as a possible fit, but as always I wouldn’t expect anything to materialize between the division rivals.