The sound of baseball crashing off a bat is often a pleasing symphony for baseball fans, but for the Toronto Blue Jays, it’s more like an echo of missed opportunities. Every time their star player Vladimir Guerrero Jr. smacks it out of the park, it serves as a reminder of what could have been. As Vladdy’s free agency approaches, fans are left wondering where things went wrong.

Vladimir Guerrero Jr., the player who has been the face of the Toronto Blue Jays for quite a while. Yet, the Jays have failed to establish a lasting, committed relationship with the slugger. The most recent opportunity where they failed to bag him was back in 2021, when Fernando Tatis Jr. signed a 14-year, $340 million deal with the Padres, setting a new standard for youngsters. Many, including baseball insider Ken Rosenthal, questioned the deal.

But now, with Tatis looking like one of the best investments in baseball, it’s clear that a similar deal for Guerrero offered right after his breakout 2021 season would have been a bargain. Instead, the Blue Jays let the opportunity pass, which in turn resulted in growing demands from Vladimir. As Rosenthal aptly noted, the Jays “had chances, well before this,” to lock up Guerrero Jr., but failed to act on them.

While the Jays might point to Vladdy’s defensive inconsistencies and his service time manipulation as reasons for delay. Those arguments only add to the growing narrative of missed opportunities.“Early on, they planned to manipulate his service time,” Rosenthal explained. “They were going to keep him in the minors; they told him he wasn’t defensively sound enough.” But he proved them wrong—his bat was always his strength, and his defense improved, eliminating one of the major concerns.

Despite all of this, the Jays’ front office continued to put off giving Vladdy an extension even though the market had a dynamic shift with massive contracts like that of Juan Soto’s. The Blue Jays’ approach, according to Rosenthal, was a series of insufficient offers and reactive decisions. It left fans to wonder why a player of Vladdy’s caliber wasn’t treated as the cornerstone he truly is.

Now, whether the Jays can keep Vladdy in Toronto would depend on their willingness to match his ask. But the road to this point has been filled with uncertainty and missed opportunities. For a team that emphasizes discipline, the Blue Jays’ failure to secure Guerrero’s long-term future is a glaring misstep. And this approach may cost them their star.

The battle for Vladimir Guerrero Jr. heats up

As Vladimir Guerrero Jr.’s free agency approaches, a fierce race is developing for his signature, with two prominent teams in the AL East emerging as strong contenders. Guerrero’s close friends have revealed that he has a strong desire to play in Red Sox Boston. He’s posted a remarkable .356 career average with 10 home runs and 44 RBIs there. With Rafael Devers and the newly acquired Alex Bregman, Guerrero could join forces with an already potent lineup, creating a dynamic core that could lead the Red Sox for years to come.

Another team that is poised to add the star slugger is the New York Yankees. With Juan Soto’s departure and the signing of Paul Goldschmidt to a one-year deal, the Yankees will need a long-term solution at first base. Vladdy’s bat would dominate at the Bronx. Moreover, the Yankees may be even more motivated by the opportunity to outbid their division rivals and prevent them from landing a franchise-altering talent.

With both teams possessing deep pockets and significant appeal, Guerrero’s decision will ultimately come down to which organization can present the most enticing offer. Will he team up with Alex Bregman, or take his services to the Yankees? Only time will tell.