Ranking the 5 most painful World Series outcomes for Blue Jays fans

Toronto Blue Jays fans have known for a while that their team won’t be winning the World Series in 2026 after coming within two outs of a championship the year before. 

That disappointment does not mean Toronto fans have to tune out the rest of October. With the Blue Jays eliminated, the focus shifts from hoping for their own championship run to watching how the remaining contenders fare—and deciding which outcomes would be the hardest to stomach.

Some teams carry familiar AL East baggage, while others have recent history, front-office connections or star-powered rosters that make them particularly easy to root against.

Here are the five teams nobody in Toronto wants to see hoist the World Series trophy

5: Cleveland Guardians

The Guardians winning the World Series in 2026 would be a shocking development that would not feel great for Blue Jays fans given their history with the team.

Toronto’s front office duo of general manager Ross Atkins and president Mark Shapiro used to run things over there, and they have continued to do business with them since leaving town. Andrés Giménez, Myles Straw, and Ernie Clement were all Guardians at one point in time. Cleveland winning after shipping all of them to Toronto wouldn't be a great look for the Blue Jays. 

4: Philadelphia Phillies

This one mostly boils down to Zack Wheeler, who took it upon himself to cause some drama when the Phillies and Blue Jays squared off in early August.

In response to accusations of Wheeler not being on the pitching rubber during his windup, Wheeler said the Blue Jays, "Have lost a lot of games (over there), so they're probably trying to pick some things up to complain about." While true, the comment felt a little like the pot calling the kettle black considering the Phillies' underwhelming performance in 2026. They fired their manager in April, after all.

One caveat to this though is Don Mattingly. Some Blue Jays fans and long-time baseball enthusiasts think it's long over due that "Donny Baseball" gets his World Series ring. On the other hand, he was a menace with the New York Yankees against the Blue Jays during his playing career and for him to get that ring one year after leaving the Blue Jays would feel bittersweet.

Nonetheless, sometimes, the great ones deserve their moment.

3: Boston Red Sox

There is no circumstance under which Blue Jays fans should ever want to watch an AL East rival win the World Series, and the Red Sox are no exception.

The fact that this Boston team is even in the playoffs is admittedly quite impressive given how poorly they started the season. They, unlike the Blue Jays, figured it out and started winning baseball games before it was too late. The problem is that they’re still the Red Sox.

2: New York Yankees

That previous statement about never wanting to see an AL East rival win applies even more to the Yankees, especially when considering last year’s intense ALDS. 

New York just played in a World Series in 2024; getting back would cement their status as the division’s true heavyweight. They’ll have their work cut out for them with Aaron Judge injured, though. Just remember what Vladimir Guerrero Jr. once said: “da Yankees lose.”

1: Los Angeles Dodgers

Does this one really need explaining? The two-time defending champions winning their third straight World Series title would be nearly impossible to stomach.

Their roster is more stacked than ever after outbidding the Blue Jays for Kyle Tucker in the offseason—which, in retrospect, looks like a good thing for Toronto—then acquiring Tarik Skubal for pennies on the dollar at the trade deadline. It will be embarrassing for them if they don't win.

There is also the threat of a lockout to consider. The Dodgers winning again would give the owners even more ammunition in their negotiations against the players as they push for a salary cap. A three-peat could genuinely be bad for baseball, regardless of any pundit who may say otherwise. 

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