Winter meetings on the agenda; here’s what to expect

ORLANDO, Fla. – The annual excuse for baseball executives to party and play golf nears.

That’s the annual winter meetings, and where it’s pretty much all talk and more socializing. This year, the assembly is scheduled for the Hilton Orlando Bonnet Creek and runs from December 8 through the 11.

Conversation, this time around, centers around free agency and the likelihood of a players’ strike after the 2026 season. All the luminaries will shine, hold court, and resolve little.

Major questions revolve around the destinations of free agents, Kyle Schwabler, Cody Bellinger, Bo Bichette, and a myriad of those who seek fortune and glory. Already, Dylan Cease is off the table. That’s because the veteran right-hander inked a seven-year, $210 million deal with Toronto.

Teams like the Los Angeles Dodgers, Milwaukee Brewers, Detroit Tigers, Toronto Blue Jays, and Philadelphia Phillies will try and place pieces of their puzzle and seek to maintain or improve their level of achievement.

Others, like the Tampa Bay Rays, Boston Red Sox, St. Louis Cardinals, and New York Yankees, seek to regain the glory of the past.

Of these teams, the Rays appear the most intriguing.

Having missed the post-season for the past two years, that was coming off five-straight post-season appearances. With the current off-season, the Rays approach the winter meetings with a significant wish list and likely tax the ability of field manager Kevin Cash to push the right buttons.

“(Last season) was a disappointing year, and we do not like having (a concluding press conference) in late September, and not in November,” Erik Neander, the team’s vice president of baseball operations, said at the end of the 2025 season. “There are many ingredients with this club that suggest that the right maneuverings from a roster standpoint and the right development from some players internally, that in 2026, we will not have this press conference in September.”

For that to happen, there appears to be a significant question facing Neander and Cash.

This is the concept of style, and how the Rays approach the game. Given power production from a limited number of players, the decision centers around the necessity to play “small ball” or rely on power production.

The latter seems unlikely, and here’s the argument.

For the 2025 season, three players could be considered as “power producers.” These players supplied the most home runs and created a significant gap between the ability to rely on the long ball and to abandon that approach.

Consider, Yandy Diaz hit. 300 with 25 homers and 83 RBIs. Then, there was Brandon Lowe with 31 bombs and 83 RBIs. Junior Camerino, at 22 years old, celebrated his coming-out party with 45 home runs (one short of the club mark set by Carlos Pena in 2007) and drove in 110 runs. First baseman Jonahan Aranda, who missed 56 games with a broken hand, chipped in with 14 homers and drove in 59 runs.

In a “what have you done for me, lately” environment, can Neander and Cash expect the same production? In a baseball world where teams constantly change and adapt, the Rays could move to another option.

That utilizes speed and pressing the defense.

The club topped the majors last season in stolen bases, and outfielder Chandler Simpson, considered the fastest runner in the game, took a league-leading 44 steals. He was also caught a league-leading 12 times.

Still, his ability to pressure a defense and outfielder Jake Mangum, who stole 27 bases, could force Cash and Neander into thinking less about power and more about manufacturing runs.

Plus, the Rays need to shore up the bullpen.

Allowing Peter Fairbanks to walk, the club starts spring training without a closer.

There could be a strong possibility that Griffin Jax, acquired from Minnesota for pitcher Taj Bradley at the 2025 trade deadline, could fill this role. Then again, it’s early in the off-season, and likely the Rays will be active to fill this critical responsibility.

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