Baseball’s history is filled with tales of unwavering loyalty and bitter rivalries. What’s new? The sudden, unexpected openness of a player whose past declarations seemed to leave no room for doubt—Vladimir Guerrero Jr., who has professed his love for Canada and the Blue Jays throughout his impressive professional career. With free agency looming, fans and media are understandably wondering what Guerrero Jr.’s future holds. Will he depart from a city, team, and country that has supported him every step of the way?

The question of where Guerrero will take his talents is eagerly in the air, while the 25-year-old said, “If I go to free agency, every team, all 30 teams, are going to have the opportunity to sit down with [me], to talk to me.” Although it would take an enormous bag of money to pry Guerrero Jr. away from the Blue Jays, his comments signal that he is indeed interested in hearing what all 30 MLB teams have to say, including the New York Yankees, the team with which his family shares a history of contradictions and conflict.

Guerrero Jr.’s beef with the Yankees is centered on an old score regarding his father, Vladimir Guerrero Sr. In late 2003, when Guerrero Jr. was 3 years old, the Yankees planned to sign the Hall of Famer but backed out at the last minute for Dwight Gooden’s nephew, Gary Sheffield. It was a grudge that legends say the Guerrero family has not let go. “It’s in the past,” Guerrero Jr. said, but insiders rumor the incident still lingers.

From ‘never’ to ‘maybe’? Vladimir Guerrero Jr. and the Yankees’ history

Guerrero Jr. has voiced his distaste for the Yankees several times. In a separate interview, Guerrero Jr. had stated,

“I would never sign with the Yankees, not even dead,” during a fan event in 2019 that preceded his young major league career, noting, “They didn’t treat my father well,” in reference to the Yankees’ botched deal with his Hall of Fame father, Vladimir Guerrero Sr., in 2003. Now, the question is: Will the Yankees be able to mend old wounds and secure the services of this generational talent? Only time will tell.

But if yes, it wouldn’t be the first time a player crossed a rift for the sake of professional advancement. Do you recall Roger Clemens signing with the Yankees after his stint with the Toronto Blue Jays, or Johnny Damon leaving the Red Sox for the

Yankees? These are examples of how players prioritize their professional goals over old rivalries. Guerrero Jr. may very well follow that script in his career someday. After all, it will not be a one-sided benefit; New York’s lineup is aging faster than a banana in the sun.

The Yankees are facing some competitive needs in the market. Other teams too, such as the Mets (Juan Soto recently acquired) and

Red Sox (Alex Bregman recently acquired), are aggressive, needful, and have set a high bar. The Dodgers hold an aggressive, bottomless pocket too. At a time like this, with Aaron Judge’s prime twilight shrinking, Guerrero Jr.’s powerful righty bat is a must-have for the Yankees to stay competitive and retake their former prominence.

The Blue Jays aren’t going to give up easily, but Guerrero’s “30 teams” comment implies divided loyalty. So, where do you think he will land—the pinstripes, a Toronto encore, or a dark horse? Let’s hear your take below.