If you thought the Blue Jays’ World Series loss was tough to swallow, just wait, because things might get even more complicated. Remember when Vladimir Guerrero Jr. said earlier this year that he wanted to stay with a “winning team”? Well, while Guerrero seems likely to stick around in Toronto for the long haul, that might not be the case for some of his teammates.

Despite their efforts to turn things around since their last title in 1993, the Jays still can’t quite shake off the losing team label. And that could have serious consequences this offseason. According to recent reports, Toronto could be facing one of its biggest challenges yet in keeping its winning core together. Guess what, don’t be surprised seeing a few big names donning rival jerseys!!!

“After Bichette, the bulk of Toronto’s offseason work will come in the rotation. Chris Bassitt, Max Scherzer, and Shane Bieber (assuming he opts out) are set to enter free agency,” Mitch Bannon reports via The New York Times. Well, every offseason brings lineup shakeups, but for the Blue Jays, this one could be especially significant.

First up is Bo Bichette, as his contract expires this year. And according to Spotrac, he could command an eight-year deal worth more than $186 million in free agency. Notably, the 27-year-old has been one of the team’s most reliable hitters. He owns a career slash line of .294/.337/.469 with 111 home runs and 60 stolen bases over seven seasons.

And this season alone, he hit .311 with an .840 OPS. Thus, continued to be one of the few Blue Jays who can consistently handle high-velocity pitching.

Then there’s 41-year-old Max Scherzer. His one-year deal is up, and he’s also headed to free agency. Sure, a 5.19 ERA might not jump off the page, but his clutch performances, especially in ALCS Game 4 and World Series Games 3 and 7, proved he still has something left in the tank.

So now, add to that the potential losses of Chris Bassitt and Shane Bieber, and the pitching depth that carried Toronto this season could evaporate quickly. Like it or not, this was probably the Blue Jays’ best shot at a championship in years. And if they can’t keep their core intact, their chances next season might take a serious hit.

The Blue Jays are also spoiled with choices

Despite losing the World Series, the Jays are now clear about what a reliable lineup could do. And considering they are set to lose a few good names, the Jays are expected to be aggressive in the upcoming offseason. And we expect their focus will be more on getting some reliable arms.

According to MLB.com’s Mark Feinsand, the Blue Jays could be in the mix for Padres pitcher Michael King. Why? Since transitioning from the bullpen, King has quietly become one of the league’s most reliable starters. He put up a 3.10 ERA over two seasons in San Diego’s rotation. And despite his shoulder nerve issue and a knee problem, he has declined his $15 million mutual option and hit free agency.

So, if Max Scherzer departs, King could give Toronto another experienced arm on the mound.

There’s also talk about Framber Valdez. He was shaping up to be one of the top starting pitchers in this year’s free-agent class. Before injuries slowed him down, Valdez went 11–4 with a 2.62 ERA and 141 SOs across 134 innings. These numbers are enough to make him a highly sought-after option.

Of course, for now, all of this is still rumor mill chatter. But with the Blue Jays expected to free up around $40 million as several players hit free agency, a bold move or two could put them right back in contention heading into 2025.