The Offseason Monitor: Winter Meetings Preview
Diving into some of the storylines going into this week's Winter Meetings
We are back with another edition of The Offseason Monitor, and this week, the baseball world is headed to Orlando, FL, to kick off the Winter Meetings. Honestly, it feels like a massive amount of action will take place this week. The stove has already been hot and laid some of the groundwork for what’s to come. Every team has something to do, some front office exec has something to prove, and one massive deal will go down when we’re all asleep at 2:15 am. That’s just how this week goes.
Let’s take a look at some upcoming story lines and see if we can make any correct predictions that will take place.
FREE AGENTS BATS ON THE MOVE
Kyle Schwarber
Prediction: Philadelphia Phillies - five-year, $140 million (AAV: $28M)
It has been reported that Schwarber is expected to sign before the end of the Winter Meetings. Which team will it be? It is widely anticipated that Schwarber will re-sign with the Phillies, but he has been linked to a few other teams. The Cincinnati Reds, Boston Red Sox, New York Mets, and, we cannot forget, the Pittsburgh Pirates have all checked in on the 33-year-old DH. Cincinnati is Kyle’s hometown team, and if he can replicate his 2025 season - absolutely electric in Great American Ballpark.
Although it seems likely that Philly will retain Schwarber in their lineup as they continue to push for October success. Their depleted farm system lacks a true power hitter knocking down the door, so losing Schwarber would be a huge blow. Philly gives him an extra year to put their deal above the rest and keep their DH.
Kyle Tucker
Prediction: Toronto Blue Jays - eight-year $328 million (AAV: $41M)
As an Orioles fan, this would pain me to see, but it does seem likely. Just this past Wednesday, Tucker was at Toronto’s Florida facilities touring his potential new spring training home.
Other suitors include the Dodgers, Yankees, Cubs, and the Phillies. The Dodgers obviously have a lot of money tied up and deferred, but are in desperate need of corner outfield help. I could see LA offering more years at a lower AAV with deferrals, obviously. The Yankees have spent a ton of money on their rotation the past few seasons, so it would make sense to grab a bat as significant as Tucker’s. Before we get ahead of ourselves, Hal Steinbrenner has publicly said that he would prefer the payroll to go down. They will more than likely try to retain Bellinger at a lower AAV. The Cubs gave up a lot of capital for a one-year rental of Tucker. In Cubs history, they have never handed out a contract worth $200+ million. Tucker exclaimed that he loved the culture around the team and game day in "The Friendly Confines." Granted, if the Phillies keep Schwarber, they will not be on the table for Tucker’s best and final offers.
The AL East is already a bloodbath as it stands now, and adding Tucker into the mix will make it that much more interesting. Toronto has the resources to outbid almost anyone to make itself a World Series winner. Now they are more attractive than ever for incoming free agents.
Bo Bichette
Prediction: Detroit Tigers seven-years $210 million (AAV: $30M)
Bichette will have an interesting pool of interest. I do not think he will sign during the meetings, though. At age 28, he is one of the younger players on the market. A homegrown Blue Jay, Bichette has been almost everything you can ask for in a player. It will be extremely hard to see Bo in a different jersey, but if Toronto lands Tucker, I think they will be fine letting Bichette walk. Andres Gimenez played well at shortstop, and they have Ernie Clement and postseason legend Addison Barger to fill in the infield.
Among the Tigers, the Braves, Yankees, and, of course, the Dodgers are in the mix for Bichette. Detroit missed out on the Alex Bregman sweepstakes last offseason and will be looking for an impact bat to plug into their lineup. Shortstop was a weak spot for Detroit last season, and even with mediocre defense, they will give Bo the keys to the position. I believe Atlanta will look to spend elsewhere, as they prioritize defense at the position too much to make that large an investment in Bichette. They allowed Nick Allen to play shortstop all season; he couldn’t hit water falling out of a boat. That tells you how much Atlanta prioritizes defense. The same rule applies to the Yankees as before. I cannot see them spending $30 million on a shortstop. The Dodgers will be the Dodgers. If Bo cannot hash out a deal with any other teams, LA will gladly take Bo with open arms.
FREE AGENT PITCHERS ON THE MOVE
Framber Valdez
Prediction: New York Mets four-years $115 million (AAV: $28.75M)
Framber is about as consistent as they come. You know what you get every fifth day when he takes the bump. The Mets need a consistent anchor they can plug into their rotation. The whole cross-up situation that took place in Houston when Framber disregarded a curveball signal and threw a fastball right into his catcher’s chest plate could impact his final accepted contract. I do think some clubs include a club/mutual option in their deals to provide insurance if he is a clubhouse cancer. Valdez and his agent attended the GM meetings last month in what I guess is an attempt to plead his case and reason with the lack of judgment.
Obviously, the Braves and Orioles will be among the best and final offers Valdez must decide between. Both squads are looking to bolster the front of their rotation. For the Braves, life after Chris Sale is coming soon, and Valdez will slot into the lefty ace without skipping a beat. They have plenty of young arms that can benefit from his tutelage as well. In the case of the Orioles, Mike Elias has a shopping list this offseason that includes a front-line starter. Their rotation has been plagued with injuries for the past 2 seasons and needs an anchor to provide guaranteed innings. Kyle Bradish and Trevor Rodgers would be a great SP2 & 3 behind Valdez. San Francisco has also been linked to Framber, but it has been reported that they are hesitant to sign “high-priced long-term starting pitchers”.
Ranger Suarez
Prediction: Houston Astros - four-years $80 million (AAV: $20M)
Suarez is coming off a career year in terms of innings pitched. At only 30 years old, he will undoubtedly be looking for a longer-term insurance policy. Injuries have come frequently, twice in 2025 (groin & back), twice in 2024 (back, undisclosed), twice in 2023 (elbow, hamstring). In between these injuries, Ranger pitches exceptionally well.
Houston will be looking for someone to replace the innings they lost from Framber Valdez. Ranger will obviously need to stay healthy (something he hasn’t done the last three years) to achieve coming close to 200 IP. I think offering a fourth year to Ranger will be enticing and will seal the deal for the Astros.
Baltimore does not need another injury-prone starting pitcher. They need some durable options that are a staple every fifth day. There are other options out there to fit that role.
Suarez has expressed interest in coming back to Philadelphia, but how much can they honestly spend? Their 2026 projected payroll is already around $240 million, and if they add Schwarber back to the fold, there might be no room at the inn for Ranger. The Phillies could slot Andrew Painter in the rotation as their top pitching prospect.
Atlanta, as I said before, will be looking for Chris Sale’s replacement soon. Ranger at his best will be a great addition to this Braves rotation, which seemingly always gets the most out of their staff.
Edwin Diaz
Prediction: Los Angeles Dodgers - four-years $75 million (AAV: $18.75M)
Diaz was back to form after a down 2024 season. In 2025, Edwin recorded 28 saves and earned the NL Reliever of the Year award. The big bad Dodgers are going to sign someone this offseason; they might as well get the best closer on the market. Tanner Scott was abysmal in the closer role this past season, blowing 10 saves.
The Mets are obviously going in a different direction, signing Devin Williams. A back-to-back punch of Williams and Diaz would be filthy. Although it is a fun dream, it is unrealistic. The Mets have other needs in the lineup to spend on, including keeping Pete Alonso around.
In the Northside of Chicago, the Cubs have a closer in Daniel Palencia. An absolute flamethrower that racked up 22 saves in 2025. Edwin Diaz stepping in that role would further lock down their back half of the game, no questions asked. But would it make sense? The Cubs need to spend to attempt to keep Kyle Tucker around. If they lose the Tucker sweepstakes, it makes sense to shorten the game, adding another great bullpen arm.
POTENTIAL TRADES
It has been reported that we could see names like Jarren Duran, Kodai Senga, Brendan Donovan, and more could be on the move. Here is what I could potentially see unfold this week
MacKenzie Gore blockbuster to Baltimore
Personally, I would love to see this happen. I would send Cade Povich, Colton Cowser, and breakout prospect Nate George in return. Gore will stabilize this rotation into a three-headed monster with Bradish and Rogers. Washington will get back Povich, a project starter with 4 years of control remaining, Cowser, an immediate impact bat in their lineup, and a fast-rising prospect in Nate George. The Nationals will look to make the most of Gore, and Baltimore is obviously in need of high upside starters.
Freddy Peralta headed to Queens
The Mets have more prospect capital than any other team in the Majors. Sending Brandon Sproat and Ronny Mauricio, I believe the Brewers’ asking price will be achieved. Ronny provides a young power bat that the Brew Crew has been missing, as well as a young controllable arm. Freddy is a one-year rental that the Mets could pivot to instead of signing a starting pitcher this year, ensuring they stay in the hunt for Skubal next offseason without committing major money long-term in 2025.
With big-name free agents still choosing their futures, contenders hunting for that final piece, and a handful of teams ready to shake up the trade market, Orlando should deliver the chaos we’ve all been waiting for. The Offseason Monitor will be here to break down every move as it happens.