The Toronto Blue Jays are not afraid of bold moves. Over the years, they’ve taken many high-stakes gambles. Some paid off spectacularly, like their blockbuster trade for Josh Donaldson in 2014, which led to an MVP season. Others that backfired, like the seven-year, $131 million extension in 2021 they signed with José Berríos. This time, the ace they are playing with is named Vladimir Guerrero Jr.

Guerrero Jr., their homegrown superstar, is entering his final year under team control. The extension deadline came and went without a deal. A Blue Jay since he was 16, Vladdy had made his intentions clear: “I want to be here. I want to be a Blue Jay for the rest of my career.” 

And where will Guerrero Jr. end up? If rumors are to be believed, plenty of teams are interested in him. Two of the biggest names are the Boston Red Sox and the New York Mets. Another in the mix are the New York Yankees, a team he once said he wouldn’t ever join. Wherever he ends up going, or not, it will be a critical year and decision for Guerrero Jr.

Both Guerrero Jr. and the Blue Jays had numbers in mind that did not match. Guerrero Jr. reportedly turned down a $350 million extension, instead eyeing a deal closer to $500 million, in line with recent megadeals signed by elite players like Juan Soto. With negotiations stalled, Guerrero acknowledged the reality of his situation.

“They expressed what they had. I expressed what I had. I’m here, and we didn’t get an agreement,” Vladdy said. “Now, they’re going to have to compete with 29 more teams.” 

The Blue Jay’s offseason moves, with the additions of Andrés Giménez, Anthony Santander, Jeff Hoffman, and Max Scherzer, are signs that they are all-in for the playoff push. If they were to trade their best hitter in the middle of the season, what message would that send?

It’s not a rare situation for a team. Other teams have been here before. But some have taken different paths. In 2021, for example, Chicago Cubs, with nine games out of a playoff spot traded Anthony Rizzo and Kris Bryant for younger prospects. Whereas, in 2023 Los Angeles Angels went all in, keeping Shohei Ohtani even when their postseason odds were slipping away. We all know how that move ended.

If Toronto is still in the race by July, this gamble could be a masterstroke. But if things fall apart, they’ll have to live with the fact that they let Vladimir Guerrero Jr., one of baseball’s brightest stars walk away for nothing.

Guerrero Jr’s future as a Free Agent

Guerrero Jr will now follows in the footsteps of the likes of Shohei Ohtani, Aaron Judge, and Juan Soto, treading the free agency waters and exploring what the market has to offer.

He has made it clear time and again he wants to win. “(A) Winning team. That’s what I’ll be looking for in free agency,” he’s said. “As you guys know, my dad played a lot of years. He never won a World Series. My personal goal is to win a World Series and give the ring to my dad. That’s all I’m looking for.”

For now, the Blue Jays have rolled the dice. They can trade Vladimir Guerrero Jr. to secure a longterm, younger talent. Who knows, he could turn out to be the new face for the franchise in the years to come. Or they could keep holding on to Guerrero, hoping for one last home-run. It’s a classic dilemma—play it safe or go all in.