Let’s find a deal with the Pittsburgh Pirates

As you know by now, Ben Cherington has left his gig as the Blue Jays’ vice president of baseball operations in order to become the new general manager of the Pittsburgh Pirates.

Good for Ben! While it sucks to lose talented members of your front office, it’s just a reality of professional sports. If your office is loaded with good people, they’ll get poached by different organizations when openings arise.

While we don’t exactly have the best view of what Cherington did with the Blue Jays, it’s known that he played a key role in building the Jays’ farm system and planning their player development strategies. His work in Toronto helping build a deep farm system coupled with his time in Boston, it’s no surprise that Cherington is getting another chance somewhere else.

Pittsburgh is a small-market team that badly needs to undergo a rebuild, so Cherington being the guy to steer the ship makes a lot of sense there. When he was promoted to GM of the Red Sox, one of the most impressive things he did was shed over $200 million in salary by sending Josh Beckett, Carl Crawford, and Adrian Gonzalez to the L.A. Dodgers after Boston’s miserable 2012 season. Of course, he also put together the team’s young core of Mookie Betts, Xander Bogaerts, Rafael Devers, and Jackie Bradley Jr. that helped them win the World Series in 2018, but I bet that Pirates ownership is more excited about the former than the latter right now.

I imagine we’ll see something similar in Pittsburgh as Cherington steps into the driver’s seat. Though the Pirates don’t have hundreds of millions of dollars in bad free-agent decisions to dump as the Red Sox did, we’ll very likely see Cherington tear down what the Pirates do have on the Major League roster in order to kick-start their rebuild. 

So, where do the Jays fit in here? Well, given that Cherington just spent three years building up a farm system in Toronto, he’s surely going to have prospects here that he wants to bring to the Pirates organization. These are two organizations moving in opposite directions, and, given the front office link, there might be a deal to be made.

Now the difficult part. Who plays for the Pittsburgh Pirates? Uhhhh… I mean, there’s a reason this team won 69 games last season. There’s a whole lot of junk on the roster. Did you know that Mely Cabrera was still playing? What about Francisco Liriano? Hey, look, Joe Musgrove, a guy the Jays traded for J.A. Happ in 2012, led the team in innings! Holy shit, that’s who they got back for Gerrit Cole?! Yikes!

Anyways, looking up and down the Pirates’ roster, there are a few quality players and some possible reclamation projects the Jays could be interested in.

There are a few other names worth talking about, but these are the three I expect to hear talked about the most this off-season. Starting pitchers like Trevor Williams and Joe Musgrove would also be nice additions to continue adding depth to the Blue Jays’ rotation, but, given the fact they’re hitting arbitration for the first time this year, I can’t see Cherington being in a rush to move them. It’s more the expensive names like Archer and Marte I would assume get moved before next year.

But are any of them worth it for the Jays? Given how much cash Toronto has to throw around this off-season, why would they need to give up prospects for Bell or Marte when they can just spend money to sign Eric Thames or Marcell Ozuna? If the Jays do go the trade route this winter, I hope we see something along the lines of signing Yasmani Grandal and trading Danny Jansen for a starter rather than giving up prospects in order to buy cheap-ish players from a team like the Pirates.