Starting pitching and the outfield are the two most glaring needs on the Blue Jays roster this offseason. If they get creative, they could fill both voids (or at least part of that void) in one fell swoop.

Meanwhile, the Boston Red Sox are reportedly a team looking to subtract. Yes, it’s this bizarre phenomenon among contending teams who are aiming to get under the luxury tax threshold. The Red Sox are projected to run a $211 million payroll in 2020, which exceeds the $208 million threshold.

Alex Speier of the Boston Globe laid out why the Red Sox are ultra-motivated to get under that $208 million threshold in 2020; because it will reset their penalty structure and could save them $90 to $100 million over the next three seasons.

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The Toronto Blue Jays, meet the Boston Red Sox. Let’s make a deal, shall we?

The Red Sox have five players making more than $20 million in 2020. The Blue Jays have a need for starting pitching, but they could sorely use some help in the outfield. The Red Sox need salary relief; the Blue Jays need players; so why not send David Price and Andrew Benintendi over to the Blue Jays?

Price has three years and $96 million remaining on his contract. Benintendi is arbitration eligible for the first time in his career and is under team control for three more seasons. As much as it might pain the Blue Jays to take on nearly $100 million remaining on Price’s contract, isn’t it worth it if Benintendi is included in the package?

There’s a lot to love about Benintendi; he’s only 25 years old, he’s a left-handed bat, a top of the order hitter and he and can handle the left field position capably (and has filled in at centre field periodically). There’s a lot of upside for a player his calibre and he would bring some balance to the Blue Jays’ right-handed heavy lineup.

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The Price aspect to this proposed trade is where it gets messy. The Blue Jays are still paying off the rest of Troy Tulowitzki’s contract, and given Price’s age and injury history over the last few years, he could be headed down the same path.

By all accounts, Price is healthy enough to pitch, and even though he wouldn’t be the Price 1.0 of the magical summer of 2015 in Toronto, at the very least, he’s still a middle-of-the-rotation starter who can eat up innings. After signing Tanner Roark, the Blue Jays seem to bulk up on those types.

The inter-division trade could be a stumbling block as well, but as Ross Atkins mentioned many times, the Blue Jays have a tremendous amount of payroll flexibility. If the team isn’t willing to pony up big bucks for free agents, they should look at opportunities to take on some bad contracts if it brings back an impact player.

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This is the exact scenario where the Blue Jays could capitalize on a division rival looking to get under the luxury tax threshold.

It’s difficult to predict what the Blue Jays would need to give up in order for this trade to make sense for the Blue Jays. Toronto would surely take on most or all the salary coming from Boston, which would tip the scales towards the Blue Jays. Add Benintendi to the mix and the Jays need to part with something significant in return.

Just spit balling here, but something centred around Reese McGuire and Eric Pardinho might make it happen. That’s some form of a pitching prospect and a player off the Blue Jays’ big league roster, but that’s the most realistic deal I could see happening.

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From the Blue Jays’ perspective, if they were to take on Price’s contract, I think it would come with the pretense that he may need to be bought out down the line. Again, it’s only through the 2022 season anyway, which might be right around when the Blue Jays are hoping to become a contender again.

This deal isn’t so much about helping a division rival or enabling them to get under the luxury tax threshold so much as it is the cost of doing business to bring back a player like Benintendi. In any other scenario, the Blue Jays would need to give up A or A+ prospects for Benintendi, but including Prices’ albatross contract in the deal negates the high prospect capital.

To be honest, I wouldn’t expect this Blue Jays front office to make a deal like this, but it’s definitely a deal they should consider. If the Red Sox are trying to trim payroll and they’re willing to include an impact player to make it happen, it makes complete sense for the Blue Jays to do it.

For the front office, a deal like this might also foster some goodwill, bringing back a fan favourite like David Price (even though it might be four years too late). And if he can toss 140-ish innings and post a 115-ish ERA+ in 2020, then it’s a fair deal for the Blue Jays.

Not that Price would be a long-term fixture in the Blue Jays starting rotation, but he could provide some stability to a pitching staff in dire need of some veteran innings.

The Blue Jays have already experienced how crazy spending can get in free agency, and also how difficult it can be to lure free agents to Toronto. They know how much Price signed for in the winter of 2015 when he went to the Red Sox. If Benintendi continues on his current career trajectory, he can expect to make $150 million or more in free agency.

This is sort of a low-key comparable to the Marlins trade in the winter of 2020. After spending a boatload on payroll the year prior, the Marlins offloaded many of their big-money contracts and the Blue Jays took advantage of the opportunity.

The Red Sox aren’t going into full-on fire sale mode, but if this opportunity brings in Benintendi, it might be too good to pass up for the Blue Jays.



