Vladimir Guerrero Jr. extension puts to rest any Red Sox speculation

Vladimir Guerrero Jr. extension puts to rest any Red Sox speculation

Vladimir Guerrero Jr. has always hit well at Fenway Park, but for anyone still fantasizing about the Toronto Blue Jays star coming to Boston, that dream is dead.

The Blue Jays officially announced their historic 14-year, $500 million extension with Guerrero on Wednesday, likely ensuring the star slugger spends the rest of his career in Toronto.

“If I tell you it’s not a big relief I’d be lying to you,” Guerrero told reporters at Fenway Park following the announcement. “It’s always been my goal to be here and I feel like I accomplished that and I’m very happy to stay here and be a Blue Jay.”

Guerrero was originally set to hit free agency following the season, and rumors had begun circulating that if he did not return to Toronto, Boston would be one of his preferred destinations. It looked likely that Guerrero would hit the open market once his self-imposed Feb. 18 deadline passed without a deal, but the two sides ultimately re-engaged.

MLB notes: Would signing slugger Vladimir Guerrero Jr. make any sense for the Red Sox?

Now instead of changing uniforms, Guerrero will remain a thorn in the Red Sox's side for years to come.

Besides making a historic financial commitment, Toronto was able to get the deal over the finish line thanks in part to a unique contract structure that could give Guerrero more bang for his buck in the long run. The deal reportedly contains no deferred money, and according to Ken Rosenthal of The Athletic, more than half will be paid out in the form of a signing bonus.

How much? $325 million.

Rosenthal reports that the signing bonus won't be paid out all at once and will instead be spread out over the life of the contract. Guerrero will reportedly receive $20 million up front, with the rest being paid out in various amounts later along with his annual salary. Because signing bonuses are included in the calculations of a player's average annual value for luxury tax purposes, Guerrero will still count for $35.71 million against the luxury tax even if the actual amount he's paid in a given year is different.

Having so much financial value paid out as a signing bonus would have two potential benefits to Guerrero. One is the fact that signing bonuses are allocated to a players state of residence, which is Guerrero's case is Florida. Because Florida does not have a state income tax, he stands to save millions of dollars.

The other benefit is that signing bonuses are not contingent on performance of services, so if Major League Baseball experiences a work stoppage after the current Collective Bargaining Agreement expires following the 2026 season, Guerrero would still be paid his bonus even if games wound up being cancelled due to a lockout or strike.

It would also protect Guerrero if games were ever cancelled for any other reason, like another pandemic.

Had Guerrero hit free agency, he would have been the top position player available and a potential franchise-changing talent. Still only 26 years old, Guerrero is already a four-time All-Star, a two-time Silver Slugger winner and a Gold Glove recipient who came into Wednesday's game with a career .287 batting average, 160 home runs and an .860 OPS since making his MLB debut in 2019.

His numbers at Fenway Park are also fabulous. In 48 games entering Wednesday he's batted .351 with 10 homers, 44 RBI and a 1.037 OPS, his best numbers at any MLB park where he's played 10-plus games.

It's not hard to see why adding a player like Guerrero would have been attractive for the Red Sox, but there would have been other challenges that might have made any potential deal unlikely.

The biggest roadblock would have been the fact that the Red Sox already have a young up-and-comer in Triston Casas playing first base who the club believes could blossom into a premier power threat as well. Boston has also shifted Rafael Devers to designated hitter, and considering he'll still have another eight years remaining on his franchise-record 10-year, $313.5 million deal after this season, giving an even bigger deal to another player who might need to shift to DH eventually would have made for a questionable distribution of resources.

Either way, it's a moot point now. Guerrero will be a Blue Jay for life, and the Red Sox are going to have to get used to dealing with him whenever Toronto comes to Fenway Park over the next decade.

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