Did the Blue Jays break the Red Sox’s chances against Vladimir Guerrero Jr?

The Toronto Blue Jays have chosen not to go out quietly this offseason, and that could have a direct impact on the Boston Red Sox and their potential pursuit of landing four-time All-Star Vladimir Guerrero Jr.

Toronto signed free agent outfielder Anthony Santander to a five-year, $92.5 million contract in free agency on Monday, according to ESPN’s Jorge Castillo. Immediately, the middle of his lineup, which had the fifth-fewest home runs (156) among all teams in baseball last season, improved dramatically. Santander is coming off a career-high 44 home runs as a first-time All-Star with the Baltimore Orioles in 2024.

Satander’s ascendancy and Guerrero’s entrenched power could create the deadliest duo in the American League East. This potential not only poses a threat to the division’s pitching staffs, including Boston’s, but it also allows Guerrero to consider staying with the Blue Jays for the long term. Guerrero is targeting the start of spring training, which for Toronto is Feb. 13, as the deadline to get a deal done.

If the Blue Jays fail, it will be up to Guerrero to decide whether the 25-year-old hits the open market as an unrestricted free agent next offseason.

The Red Sox have already been linked to Guerrero as a destination the two-time Silver Slugger winner “would love” to join, according to Bob Nightingale of USA Today. Guerrero has a lot of respect in the Boston clubhouse and almost joined franchise star Rafael Devers in the 2023 World Baseball Classic with the Dominican Republic team.

Boston failed to sign another Dominican native and 2023 WBC team member in Juan Soto, demonstrating its willingness to open its wallets in free agency.

Toronto has also had its share of failures when it comes to free agency. The Blue Jays secured a meeting with two-way phenom Shohei Ohtani last offseason, and this go-around the franchise failed to sign international free agent pitcher Roki Sasaki – who joined Ohtani and signed with the Los Angeles Dodgers instead.

However, this offseason, Toronto has not fallen completely empty.

Santander, despite signing late in the offseason, entered the market as one of the best hitters available. The 30-year-old veteran has spent each of his eight career seasons playing in the American League East, making Santander no stranger to Toronto’s Rogers Center and Boston’s Fenway Park.

Guerrero has never won a playoff series, going 0-for-3 in the AL wild-card with the Blue Jays and missing the postseason completely last season. Toronto finished 20 games behind the division-leading New York Yankees and 12 games behind in the wild-card race, preventing one of baseball’s brightest hitters from performing on its brightest stage .

Toronto, under Guerrero extension deadline, expected to feel pressure to lock its local star soon. However, the roster upgrade could also help prevent the Red Sox from swooping in and grabbing the left-handed slugger.