For a pair of teams who share the same division and have represented the American League in the World Series a combined eight times over the last 40 years, the relationship between the Blue Jays and Red
Sox has been remarkably tame. There’s no signature clash, no recent season where one stood in the doorway and blocked the other, and no real palpable animosity between the fanbases.
In fact, one of the best baseball clips in recent memory was David Ortiz and Vladimir Guerrero Jr. bringing Red Sox and Blue Jay fans together via a joyous trolling of the Yankees following Game 4 of the ALDS in New York. (The enemy of your enemy is often your friend!)
But what if all this was about to change?
Perhaps this week, with both teams making strong swings to improve their rotation just over 24 hours apart, we’re seeing the first signs of the gathering storm.
First, it was the Sox trading for Sonny Gray on Tuesday.
And then it was the Jays officially inking Dylan Cease on Wednesday night.
There’s so much to dive into with these transactions, but the bottom line is this: Both the 2026 Red Sox and the 2026 Blue Jays are better baseball teams than they were on Monday (and they were both already pretty darn good).
What we have here is a Blue Jays franchise in as strong of a financial position as they’ve been at any point this century, and a Red Sox team on the verge of a renaissance thanks to a blossoming young core that could end up being the deepest they’ve ever had.
Interestingly enough, the Blue Jays have been trying to flex their financial muscle for a few years now. They were in on both the Shohei Ohtani and Juan Soto sweepstakes (among others), but they always seemed to come up short when it came to landing the big fish.
Well, that’s certainly changing now. Back in the spring, they locked up their home grown sensation in Vladimir Guerrero Jr. for $500 million (and boy did he deliver for them in the playoffs!), and now they’ve gone ahead signed Cease for over $200 million.
If the Red Sox had made these two signings, the Guerrero contract would represent the largest in team history, and the Cease contract would be the second largest free agent deal in Red Sox team history. Oddly enough, the only larger free agent deal the Red Sox have ever handed out was to David Price for $217 million when they were actually taking him away from the Blue Jays a decade ago. Oh how baseball likes to play these poetic games.
But the swap isn’t just evident on the books. On the field, the Blue Jays just suffered one of the most devastating near miss defeats in the history of the sport, which is something that used to define the Red Sox experience. In some ways, the Blue Jays feel like they need to have the winter the 2003-2004 Red Sox had following the Aaron Boone rip your soul out walk-off. These experiences galvanize people!
But amid all this juice north of the border, there’s something Blue Jays don’t have, and that’s a core as young and dynamic and fresh off the farm as the Red Sox. Not only that, but the Blue Jays didn’t really have to deal with the Red Sox core in 2025 despite the countless times they’ll be sparring with them in the years to come.
There wer 13 head-to-head match ups between Boston and Toronto in 2025, but Roman Anthony and Marcelo only played in one three-game series again the Blue Jays. The first two times the team met was before they were called up, and the last one was after they both went on the shelf with season-ending injuries.
Meanwhile, on the mound, the Blue Jays never faced faced Hunter Dobbins, missed Connelly Early, and never faced Payton Tolle in a start (he mopped up one inning late out of the bullpen in a blow out). Much like the Boston and Toronto franchises on a larger scale in history, the 2025 Sox prospects and the 2025 pennant winning Blue Jays team were like two ships passing in the night.
But sooner or later their paths will cross and a battle will ensue — and when this happens, it may unlock a dormant volcano of a rivalry we didn’t even realize was capable of fully popping off. Over the last 40 years, the Red Sox and Blue Jays have made the postseason a combined 29 times (18 for Boston and 11 for Toronto), and yet 2025 was only the second time they’ve made it in the same season. (The other occurred in 2016, when they also failed to meet in a playoff series.)
Now for the first time (other than maybe the late 80s), the Red Sox and Blue Jays may be about to peak in unison. And all this will occur against the backdrop of two passionate sports towns and two very large fan bases. At this point, the only thing keeping the lid on the boil is the fanbases’ mutual hatred of the Yankees …
But eventually, these two predators will find each other in the open plain.
