Two Toughest Contract Decisions Facing the Blue Jays This Winter

It is definitely going to be an interesting offseason for Toronto has they try to navigate who is leaving, retiring, and who needs to be replaced.

Blue Jays left fielder Myles Straw (3) walks toward the dugout while blowing a bubble with chewing gum and holding a bat before a game against the Athletics. Credit: Dennis Lee-Imag | IMAGN IMAGES via Reuters Connect

There are a couple of things that are certain for the Toronto Blue Jays in the coming months: they need to get a proven bat who can score runs as well as add some depth to the starting rotation.

Some of the toughest contract decisions that the front office is going to have to deal with include whether or not guys like George Springer and Max Scherzer are hanging up their cleats. But that is something that is out of their control, and they need to take a look at a couple of players who will be available.

This is a very difficult time to navigate as contracts are negotiated and new players join a club, while also seeing who should stay within an organization. The front office has two that would help make their team return to the postseason next time around.

2 Players the Blue Jays Should Lock Down for 2027

Blue Jays starting pitcher Shane Bieber (57) throws a pitch against the Rays. Credit: Nathan Ray Seebeck-Imagn I | IMAGN IMAGES via Reuters Connect

Now, one of the team can fill one hole on the roster in-house with departing free agent Shane Bieber. Bieber was much better late in the season, posting a 2.84 ERA over his final seven starts.

Nobody would expect him to step into a role in the middle of the rotation, as that will be filled by Jose Soriano, Cody Ponce, or Trey Yesavage. Bieber wouldn't take on a monumental role, but the team would definitely benefit as the No.5 pitcher.

At present, the offense wouldn't exactly benefit if the president of baseball operations, Ross Atkins, decided to pick up the club option on outfielder Myles Straw. Although Straw offers a lot more to a team than that, he would be worth having on a team.

Straw doesn't have much pop in his bat, but he always figures out how to get on base to turn the order, which is highlighted by a .410 on-base percentage in his final 30 games. That is exactly what a manager wants out of their No.9 hitter.

MYLES FREAKING STRAW ‼️ pic.twitter.com/plJycWcLBh

— Sportsnet (@Sportsnet) August 12, 2026

The club option might be a little too steep for what Straw provides, even though he can be put in defensively, as Straw has been entrusted in every spot of the outfield and a few in the infield (including pitcher).

While he does yield a nice return, $8 million in 2027 is steep, so it would be wise to renegotiate a different contract and, if the price is right, bring him back for depth in the outfield and smart plays at the plate.

Neither Straw nor Bieber will be a huge move that steals many headlines, but both would provide reinforcements to their team, and if Atkins learned anything this season, it is that there can never be too many healthy players.

It was a disappointing year to say the least for the Jays, but if they go get an elite bat and make sure that they have aid on the roster, 2027 will tell a very different tale.