Blue Jays: Toronto Columnist Says Blue Jays Should Sign Stephen Strasburgh, Gerrit Cole

Right now, the Toronto Blue Jays find themselves in a rebuilding mode. Obviously, the odds of them signing either of Stephen Strasburg or Gerrit Cole are rather low. Meanwhile, columnist Gregor Chisholm of the Toronto Star says the Jays should break the bank to sign one of the pair of aces in free agency.

However, Chisholm is a realist; and says it won’t happen. While we agree, let’s look at the reasoning behind his statement.

#BlueJays have approximately $65M in allocated salaries for 2020. The young core is still a few years away from big raises. There's a unique opportunity to front load offers to the best free agents out there. If/when they don't take it, that's on Rogers: https://t.co/F5LgYjldJ5

— Gregor Chisholm (@GregorChisholm) November 12, 2019

Interestingly, Chisholm says the Blue Jays are thought to be ‘aggressive’ this winter; which is news to me.

By most accounts, Toronto is going to be an aggressive buyer this winter and the Jays should have more financial flexibility than just about any team in the majors. If ever there was a time to take a run at the biggest names available, this is it.

The writer Chisholm continues, saying that Strasburg or Cole would help the Blue Jays contend in 2021 when they figure to be at their prime. With a talented little core already under control until that time, he figures that either of these pitchers would still be rolling in two seasons.

The annual general managers’ meetings opened Monday in Arizona, where Gerrit Cole and Stephen Strasburg figure to dominate the headlines. Both would be a perfect fit on just about any roster, but particularly in Toronto where the Jays have a young core of position players locked up long term.

The Jays aren’t ready to contend, and adding a potential Cy Young arm likely wouldn’t change that, but it would be a big step forward and increase the chances of winning in 2021. The thing is, it’s not going happen.

Indeed, Chisholm says that the Jays should be ‘aiming high’ with their target this winter. Instead of signing a Wade Miley, raise the bar and bring in the big, bad bull. He says that by throwing a huge deal at one of these two, they might consider. Especially with the tax ramifications of playing in another country.

If Rogers was willing to think outside the box, it would approve a large spike in payroll to accommodate the signing of a top free agent to a heavily front-loaded deal. Start the bidding at $40 million per year over the first three seasons and drastically cut the annual salary over the duration of the contract. Pay someone like Cole top dollar now, in exchange for flexibility later when Guerrero, Biggio and Bichette are due large raises. A side benefit of spending more upfront is that the trade value may improve with time, instead of the other way around.

He argues that Rogers is operating the Jays like a mid to lower-tier franchise, saying that Toronto should perenially be spending like a top-10 franchise in baseball. While pointing towards Manny Machado and Bryce Harper as guys who signed in surprising locations due to huge deals, he says that the time for Toronto to spend is right now; not when the young core is up for new extensions.

I agree with him there, but it’s going to be a hard sell to get a Cole or a Strasburg to just go play in Toronto. With the team not contending any time soon, these guys want to play in a luxurious location; at least I think in the case of Strasburg. However, he has a point that at a large enough contract number, the Jays could probably lure one of these two.

It would be really interesting to see Strasburg or Cole take their talents to Toronto with Vladdy Jr. and Bichette playing behind them. It’s fun to discuss and then leave in the archives of this site as they sign elsewhere. In the end, the Jays are going to need to play well, draft better, and continue to develop the guys they have on the field before becoming players in the next wave of marquee free agents in the years to come.