Red Sox lose out on big name after he signs massive extension elsewhere

The Toronto Blue Jays signed star slugger Vladimir Guerrero Jr. to a 14-year, $500 million extension, on Monday, sparing him from having to explore the open market next offseason. The 26-year-old is signed to remain in his native Canada through the 2039 season -- he will be 40 when the contract finally concludes.

Guerrero's extension is the third-highest paying contract in baseball history. Only Shohei Ohtani and Juan Soto have larger deals, according to Spotrac.

Notably, his deal has no deferred money (i.e. a traditional contract). The recent trend has been to postpone the bulk of the payment until later in the deal or even after the player has retired. Guerrero bucked the trend, so to speak.

Baseball insider Bob Nightengale wrote back in February: “It’s no secret that Vladimir Guerrero has told friends that if he hits free agency, he’d love to play for the Boston Red Sox." So, had Guerrero hit free agency at the end of the season, he may have been an option for Boston, but now those aspirations are over.

To potentially add insult to injury, the news of the extension comes as the Blue Jays arrive in Boston to face the Sox in a four-game series starting Monday night. Although Guerrero has had a slightly slower start to the season than he's used to (no homers and a .256 batting average), he's historically very strong at the plate in Fenway Park (.358 average, 10 homers, and 44 RBIs in 45 games, according to StatMuse).

With the security of the extension under his belt, Guerrero could be quite comfortable having a strong series at the plate in Boston, all over again.

Luke Graham is a digital sports content co-op for 98.5 the Sports Hub. He is currently a sophomore at Northeastern University studying communications and media studies. Read all his articles here, and follow him on X @LukeGraham05.