What you need to know as Blue Jays head to Winter Meetings

This story was excerpted from Keegan Matheson’s Blue Jays Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

TORONTO -- Most teams will land at the MLB Winter Meetings still searching for their first big move of the offseason. The Blue Jays arrive with a press conference already scheduled.

Dylan Cease’s introductory press conference is scheduled for Tuesday in Orlando, Fla., where he’ll have Blue Jays general manager Ross Atkins on one side of him and agent Scott Boras on the other. Sure, the timing lined up naturally after the Blue Jays jumped the market to sign Cease to a seven-year, $210 million deal, but it’s also a fine opportunity to take center stage and remind the rest of baseball that they aren’t going anywhere.

The Blue Jays, still barely a month removed from their Game 7 World Series loss to the Dodgers, seem determined to keep the pedal down. First it was Cease, then Cody Ponce, whom they’ve agreed to terms with on a three-year, $30 million deal, a source told MLB.com, deepening what is already one of the best rotations in baseball. They aren’t done yet.

Ahead of the MLB Winter Meetings, which officially open Monday, here’s everything you need to know:

Blue Jays needs:

One big bat: The candidates here are obvious, with Bo Bichette and Kyle Tucker sitting atop the market. With Bichette, the Blue Jays could bring back the longtime fan favorite who’s been with the organization since being drafted out of high school in 2016, and they could do so for a price that could be significantly less than Tucker’s. That said, Tucker is the best player available for a reason, an all-around offensive force who fits the Blue Jays’ identity perfectly and fills an outfield need long term.

Back-end reliever(s): Whether the Blue Jays swing big for a new closer or just choose to give Jeff Hoffman some competition, the back end of their bullpen needs an upgrade. Louis Varland is locked in as the setup man, and while the Blue Jays have done well to develop some middle relievers of their own, including Braydon Fisher, they need to be thinking about the postseason already, where teams shorten up their bullpens to three or four elite arms. That group still needs some work.

Potential trade candidates:

This feels like a short list, doesn’t it? Perhaps someone like Joey Loperfido would appeal to clubs if Toronto chooses to hit the trade market for relievers, but the Blue Jays don’t have much unnecessary excess on their roster. Keep in mind, though, that this front office has never shied away from dealing top prospects or first-rounders.

Prospect to know:

Ricky Tiedemann (No. 4) has the potential to be one of the biggest stories in Blue Jays camp … and it could happen quickly. Two years ago, he generated a ton of buzz in camp and was the club’s No. 1 prospect, but Tommy John surgery cost him part of 2024 and all of ‘25. He’s still just 23 though, and the gifted lefty will have every opportunity to fire up the hype train again. There’s not enough attention on Ricky T.

Rule 5 Draft:

The Blue Jays are always open to finding a wrinkle in the Rule 5 Draft, like they did a year ago when they selected Angel Bastardo from the Red Sox, who was still recovering from Tommy John surgery. That said, this doesn’t feel like a team that will make a selection.

Their talent will be attractive to others, though. Atop that list is outfielder Yohendrick Pinango, who ended the season ranked No. 7 in the system. Acquired a year ago from the Cubs for Nate Pearson, the 23-year-old put up a .791 OPS with 15 home runs between Double-A and Triple-A and has the mature approach that a rebuilding club could take a swing on.

Burning question:

Will Bichette return? Yes, Tucker is the better player and their contracts will show that, but there’s an emotional connection to Bichette, especially after that Game 7 home run off Shohei Ohtani.

This decision will hang over the Blue Jays’ offseason and dominate fan attention, especially if this gets to the point where Bichette leaves Toronto and lands with another club. There are some nightmare scenarios involved, like Bichette landing within the division with the Red Sox. It already feels so wrong to envision Bichette in another team’s uniform, but such is the business of baseball.

What we know for sure is that Bichette wants to continue his career with the Blue Jays and play alongside Vladimir Guerrero Jr. Money talks, though, and it’s always the loudest voice at the table.