Sep 3, 2025; Cincinnati, Ohio, USA; Toronto Blue Jays shortstop Bo Bichette (11) hits a fielder’s choice RBI in the eighth inning against the Cincinnati Reds at Great American Ball Park. Mandatory Credit: Katie Stratman-Imagn Images Katie Stratman-Imagn Images

3 Players Blue Jays Should Pursue This Winter To Bolster Roster: Too Early Edition

Originally posted on Fastball on SI | By Zach Pressnell | Last updated Sep 18, 2025 9:00 PM ET

The Toronto Blue Jays have been one of the better teams in baseball this year after making a few solid moves over the last 12 months. The biggest move the Blue Jays made was signing superstar slugger Vladimir Guerrero Jr. to a $500 million deal.

As the regular season quickly comes to a close, the Blue Jays could begin looking toward the offseason and free agency. There are bound to be some solid options available for the Blue Jays, including a potential monster re-signing.

Who are the top three players the Blue Jays could pursue to bolster their roster heading into 2026?

RHP Brandon Woodruff

The Blue Jays need to add some more starting pitching to their roster as their pitching staff grows older with each passing day. While there are some intriguing top options on the market, Toronto would be better off spending its big money on position players.

That leaves an under-the-radar star like Brandon Woodruff as the perfect option for Toronto. Woodruff likely won't sign for more than $50 million across a few years. This fits perfectly in the Blue Jays' budget, allowing the front office to go after more top talent in free agency.

RHP Ryan Helsley

The biggest hole on the Blue Jays' roster is in the bullpen. They're loaded from top to bottom, but the bullpen has continued to let them down this year. In the offseason, going after a top reliever like Ryan Helsley would be the perfect idea for Toronto. Helsley has partially tanked his value in free agency with a horrendous second half, which could work in the Blue Jays' favor. Toronto could add a few top players to the bullpen, and Helsley would be the perfect player to take over as the team's next closer.

SS Bo Bichette

The top player for the Blue Jays to go after is one of their own: star shortstop Bo Bichette. Bichette is the top middle infielder on the market this year, and the Blue Jays make the most sense as the star's incumbent team.

It would be quite an expensive move for Toronto to make, but it's necessary for its future. Pairing Bichette and Guerrero next to each other for the foreseeable future would be exactly what the Blue Jays need. The money might be tight in a move like this, but it's something the front office would need to make work if they want to compete with the New York Yankees and Los Angeles Dodgers long term.

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This article first appeared on Fastball on SI and was syndicated with permission.

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