The Vladimir Guerrero Jr. extension has left the baseball world in shock. Despite saying that Guerrero wouldn't talk extension during the regular season, the two sides agreed on a 14-year, $500 million extension just nine days into the regular season. This move makes Guerrero Jr. a Blue Jay for life, and gives Toronto a true piece to build their franchise around.
First baseman Vladimir Guerrero Jr. and the Toronto Blue Jays are in agreement on a 14-year, $500 million contract extension, pending physical, sources tell ESPN. A monumental, no-deferral deal to keep the homegrown star in Toronto for the rest of his career.
— Jeff Passan (@JeffPassan) April 7, 2025
However, this extension is not surprising just because of Guerrero's comments before the season started. One of the running jokes for MLB fans has been how the Blue Jays were always interested in big-name free agents but never able to land one. So, where did this narrative come from, and how did it affect this extension?
How past free agent failures lead to the Vladimir Guerrero Jr. Extension
At the end of the 2023 season, Toronto was coming off an 89-73 season in which they clinched a wild card berth but were swept by the Minnesota Twins in the first round of the playoffs. However, the Blue Jays front office felt they were one big move away from becoming a true World Series contender. If they could add a superstar alongside guys like Guerrero Jr. and Bo Bichette, they felt they could get back to the promised land.
Thankfully for the Jays, the best player in baseball was about to hit the free agent market in Shohei Ohtani. MLB's most popular player was coming off his second unanimous MVP season, hitting and pitching at an elite level. Although there were concerns about Ohtani getting Tommy John surgery, a team would be silly not to have interest.
For the entire Ohtani sweepstakes, the Blue Jays were one of the most talked-about teams. Right before he made his decision, Jon Morosi reported that he was on his plane to Toronto, and many speculated it was to sign a contract.
Ultimately, that report was false, and Ohtani signed with the Los Angeles Dodgers. This was crushing for the Jays specifically, as they felt they were on the doorstep of landing the Japanese legend. General Manager Ross Atkins described it as one of the worst calls he's received on the job.
Fortunately for Toronto, the 2024 offseason presented another opportunity to land a superstar, as Juan Soto was set to be a free agent. They saw it as the perfect pivot, because Soto and Guerrero Jr. would create one of the most lethal one-two punches in all of baseball.
Just like with Ohtani, the Blue Jays were aggressive in their pursuit of Soto. They met with him several times and had permission from ownership to go above their initial offer. Many reports stated that the Blue Jays were in contention all the way until the end.
Yet, for the second straight offseason, the Blue Jays failed to cross the finish line as Soto signed a mega-deal with the New York Mets. As the old adage goes in these pursuits "If you're not first, you're last."
After back-to-back offseasons of missing out on the big fish in free agency — which also included their gut-wrenching failure to secure Roki Sasaki despite being labeled as a finalist — there were concerns that the same would happen if Guerrero Jr. hit the open market. Although we do not know which teams would have been interested, we can assume nearly every team would have bid for the first baseman's services.
It was slowly becoming reality that the Jays could be outbid and face a third straight winter where they failed to sign the prize of the offseason. However, this one would be the worst because it was a homegrown star. No doubt this caused Toronto to be more willing to overpay and give Guerrero Jr. whatever he wanted to ensure he stays in the great white north.
No matter how this upcoming offseason goes, the jokes about the Blue Jays not being able to convince a superstar to accept hundreds of millions of dollars are dead.
Now, the question becomes if they can convince anyone to share the Canadian spotlight with Guerrero.