If the Pirates do go rebuild/retool and deal Cole i wonder what they would want to do with future salaries. We know McCutchen and Harrison are being shopped.
If they land Frazier in the Cole deal they will have Clint Frazier, Adam Frazier, Polanco, and Marte all in the OF. In addition to Meadows coming up. Polanco is 26 and has 6 more years of control under a pretty decent deal - his next 4 years are guaranteed at 30.4M. Has last 2 years can be bought out at 4M or his 5th and 6th year option can be picked up 12.5M and 13.5M. I would think the Pirates would likely hold onto him so he can rebuild value or be ready when they are on the rise again.
I can see Marte being dealt. 29 years old and coming off a PED suspension. Guaranteed 18M over the next 2 years with options for 11.5M and 12.5M which can be bought out for 2M and 1M. If the Pirates decided to trade Cole, Harrison and McCutchen while acquiring Clint Frazier i would think one of Marte or Polanco could be had. Polanco might be the preference due to age, contract and fit but Marte might be the only one available. Pirates might not be good for another 2-3 years and at that point Marte is 32 if they pick up his options he only has 1 year remaining. Might be worth shopping now.
Jays completed a deal for Liriano with the Pirates and have discussed McCutchen, Watson and Harrison in the past. Wondering if taking Marte and Harrison (combine 18M off their 2018 books and around 30M in guaranteed money) would interest them. Marte still is a good player so they wont be adding any prospects like the Liriano deal but he does come with some uncertainty with the PED suspension. Might be worth something to pursue.
Dealing Cole, McCutchen, Marte, and Harrison gets them to 63M next season and around the same in 2019 which can be closer to 55M if they dont exercise their option on Freese.
I agree with your logic, that acquiring a guy like Frazier as part of a potential Gerrit Cole deal would give the Pirates a surplus in OFs and thus would be looking to deal one. To me, Starling Marte is the guy that's most attractive from the Jays perspective, and likely is the guy that is most available in a trade aside from McCutchen (on the last year of his contract now). Marte adds lots of value on both sides of the ball (career 117 wRC+ and averaged 4.1 WAR in every full season), and like you mentioned, his contract is very team friendly. His PED suspension has hurt his reputation across the league and in Pittsburgh, and that along with his age (which will limit his skillset at some point in the coming years) not exactly matching the next wave of talent for the Bucs, I think he's a guy you could pry away from them. I don't think acquiring him would be cheap though.
Also, I would have little to no interest in the Jays acquiring Gregory Polanco despite the many years of control and young age. He's a career 93 wRC+ hitter, with a career high 106 in 2016. The biggest limitation is his struggles against lefties, which have limited him to a career mark of .209/.266/.325, all good for a career 59 wRC+. In theory, he's best utilized as a platoon hitter but even then, he's just a career 103 wRC+ hitter against righties. He's shown flashes of being a good hitter, and perhaps there's more there, but injuries have limited him (lots of hamstring and leg area injuries) and the idea of bringing a guy with said injuries into Rogers Center for half his games doesn't sound promising.
A guy I might be willing to take a shot on from the Pirates (doubt they are ready to move on from him but you never know) is pitcher Tyler Glasnow. Glasnow is a guy that has been mentioned among the top pitching prospects in the game for years, and despite great stats in the minors (huge strikeout numbers but also bad walk rates), he has been unable to find any success in the majors. Last year, upon Glasnow's demotion to AAA again, Pitching coach Ray Searage had Glasnow switch to the stretch full time, and this really led to improved command. His walk rate at AAA last year fell to 3.09/9 in 93.1 innings compared to 5.04/9 the year before in 110.2 innings, and 4.83/9 in 41 innings in 2015. Searage also had Glasnow change his grip on his changeup which has done wonders for it. Yes it isn't consistent as of yet but when Glasnows new changeup is locked in along with his FB & CB (both are 60+ grade pitches), he's near impossible to hit...When you add improved control to a guy with that kind of stuff (13.50 K/9 last year in AAA) you have the look of a dominant arm. A 1.93 ERA along with a 2.23 FIP and a 2.17 xFIP at AAA last year show how dominant he can be. Would be a target of mine for sure.