How Blue Jays figure to be stars of the show at baseball's Winter Meetings

ORLANDO, Fla. — As a product of the mammoth Disney marketing machine, Orlando is often proclaimed as “the happiest place on earth.”

If happiness is defined by overcrowded, sprawling amusement parks, perhaps it is.

But will the central Florida city bring more joy to the Blue Jays and their fans this week when baseball’s annual Winter Meetings get underway on Monday?

Perhaps it will.

With Toronto general manager Ross Atkins actively shopping and the Jays essentially emerging as the talk of the sport, Toronto will be front and centre here over the next three days.

The buzz from the team’s spirited run through the post season hasn’t waned – in reality, it’s arguably grown louder. The fact that Atkins has been the most active GM of the offseason only adds the glow around the Jays, who seem determined and capable of spending to remain as serious contenders.

None of this means the team will leave Florida with more shiny new toys to enhance an already promising roster. But at the least the Jays will lay the groundwork for the remaining moves on what is shaping up as one of the most captivating offseason in franchise history.

In no particular order, here’s what to expect from the three days of meetings at the Bonnet Creek Resort and Spa.

Showtime for Dylan Cease

The Blue Jays’ big-money acquisition of this offseason (so far), Dylan Cease, will be unveiled in an introductory press conference on Tuesday, one designed to further amplify the team’s big boy status.

Held in the main ballroom in front of a full complement of baseball media, the press conference will have a performative side as well. Cease will be flanked by Atkins on one side and his agent, Scott Boras on the other.

It will also have performative side for the Jays, who have been in the spotlight since that incredible run through the post season, extending the eventual champion Los Angeles Dodgers to seven games in the Fall Classic.  The seven-year, US$210 million deal Cease signed not only was the largest the team has awarded to a free agent, it served notice of the Jays’ means and intent.

While there will be questions about Cease, national media will want to probe deeper into the Jays, not only for their emergence as American League champions in 2025, but for their emergence as one of the more respected big-money teams in the sport.

It will certainly be a change for Atkins and the Jays brass who have been active in recent years, but fairly or not regarded as also-rans. The Jays are at the big boys table now with no intent to vacate.

What about Bo?

With each day, it seems, the speculation around the Jays’ Bo Bichette continues to grow, especially in the only market he has ever played.

Will the Jays step up their pursuit of their former all-star shortstop? Is he a priority? Or are they willing to move in another direction?

Will the three-run homer he hit in the third inning of the World Series’ Game 7 be his final big act as a Blue Jay?

Like any negotiation and pursuit of a prominent free agent, it’s complicated. There is an obvious attachment of Bichette to Toronto and the Blue Jays to Bichette and that could mean something.

What we don’t know is how highly the Jays place the player on their want list and how boisterous the market will be for him among the other 29 teams.

Already much of the talk around Bichette centres on whether he will be a shortstop or a second baseman wherever he lands. Obviously that uncertainty could figure into his market value given that shortstops tend to be paid considerably more than their infield neighbour.

Worst case for the Jays would be that Bichette not only goes elsewhere but lands with a division rival, a possibility if you are to buy the persistent rumours of the Boston Red Sox’s interest in Bichette.

What are the Winter Meetings?

The first week of December is the traditional home to the most important offseason gathering of baseball’s stakeholders, an event unlike anything in the major North American professional sports.

A spot for trades, free agent signings, rumours run rampant and a general opportunity for all of MLB’s major stakeholders to converge in a large convention setting.

Besides the possibility of deals happening and being announced, speculation is fuelled as the various parties — agents, management, players — pump up their agendas to a willing and captive audience.

Managers from all 30 teams, including the Jays’ John Schneider, have scheduled press conferences with the media.

General managers from each team also meet with the media daily, rarely revealing much but at least adding to the narrative of the offseason action.

As well, should a player be elected to the Hall of Fame from Sunday’s classic era committee, there will be a press conference for the new inductee on Monday.

This year, there will also be a World Baseball Classic Media Day with representatives from all the participating countries including Team Canada general manager Greg Hamilton and manager Ernie Whitt.

What’s on Blue Jays shopping list?

Much as he has been throughout the offseason to date, Atkins and the Blue Jays are expected to be front and centre in the land of Disney as they continue to build on a roster that took them to within two outs of winning a World Series.

With the starting rotation bolstered by the addition of starters Cease and Cody Ponce, logic (and industry scuttlebutt) suggests that the Jays will turn to a high-end enhancement for the bullpen and an impact bat to add oomph to the lineup.

Does that mean the team is looking for a replacement for Jeff Hoffman? Potentially, though the Jays still value last year’s closer as a high leverage arm. The need (and desire) is to acquire another arm to at least complement Hoffman, however.

Duelling with that need and quest is Atkins’ pursuit of adding a big, impact bat to further enhance the lineup. (Hello Bo Bichette and Kyle Tucker.)

Rumour central

As fans and observers are well aware, the baseball offseason is like no other. A long, drawn-out free agency period is stoked by rumours and speculation that essentially keeps the sport in the headlines from the final out of the World Series until a few weeks before pitchers and catchers report for spring training.

Much of the talk is fuelled by agents with obvious and clear agendas — to fire up interest (and bidding) in their clients. But teams will play the same game, with general managers acting coy or indifferent to help their own cause.

(As an aside, Atkins is one of the best poker players in the business when it comes to this. Rarely does he hint at what’s in his hand and the Jays front office is generally leak-free when it comes to releasing information until a deal or signing is complete.)

In recent years, the amount of big deals announced during the meetings have been few, but at the least the time spent in close proximity accelerates the process.

Both Shohei Ohtani and Juan Soto, for example, signed their deals with the Dodgers and Mets respectively, within a week of the Meetings conclusion.

Top of the market

The 2025 version of the Winter Meetings is somewhat downscale compared to the two most recent editions.

In 2024, Blue Jays fans and the rest of the baseball world recall, the Ohtani sweepstakes were reaching the fevered stage and a year ago it was Soto that topped the fancy of big shopping teams.

The Jays were said to be “in” on both of those stars — a common refrain in recent years as owner Rogers has committed to being a big player in terms of spending. No longer are the Jays viewed as pawns in the negotiations, however, even if that characterization was unfairly exaggerated.

This year, the big news swirls around Kyle Tucker, a top-hitting outfielder who may not have the cache of the showstoppers the previous two years, but is rightly viewed as an impact bat that can be the top of any offence.

The 28-year-old has been an all star each of the last four seasons and will be rewarded handsomely for his elite skills and versatility. Tucker is expected to land a multi-year contract north of US$400 million.

So what about Tucker, then?

Much was made about Tucker’s visit to the Jays player development complex in Dunedin last week, an easy drive from the corner outfielder’s Tampa home.

It’s a routine move for prominent free agents, a point the Jays want to hammer home. That said, it’s difficult not to forget the mysterious visit Ohtani made to the Jays facility almost two years ago to the day.

Landing Tucker would be a huge move for the Jays, both for the short and long term. There is a clear need for an impact bat with Tucker and Bichette the two most obvious options.

If it’s Tucker, the Jays would get a high contact, low strikeout hitter that would be a good fit at the top of the order. They’d also have a long-term productive bat to complement Vlad Guerrero Jr. for what many are expecting to be a lengthy competitive window going forward.

Though the Jays have been among the more prominent suitors mentioned for Tucker, nothing is guaranteed given that the market has yet to truly accelerate.

The downside for the Jays — if there is one — is that it’s extremely unlikely that they could afford both Tucker and Bichette.