It’s the most wonderful time of the year! Except for Opening Day. It’s the Major League Baseball Winter Meetings taking place this year in Orlando. Team executives get together to discuss trades and player’s agents roll into town looking to get their clients gainfully employed; very gainfully! Then, it all wraps up with the annual Rule 5 Draft on Wednesday afternoon.

Git ‘er done!

Kyle Schwarber and his agent Casey Close will be a big topic of discussion. The Phillies, Reds and Red Sox figure to be the most prominent suitors, but you can never count out other teams jumping in. Reports are that Schwarber wants to get a new deal for next year wrapped up sooner, not later, and that would work perfectly for the Phillies and other teams who are waiting for the first domino to fall so they can figure out if they have to turn to Plan B or not. The Phillies are particularly waiting for the Schwarbomb to be launched. If they can re-sign Schwarber, they can start to answer other questions about the team like the outfield, catcher, bullpen and possibly another starting pitcher. If they do win the sweepstakes though their available money falls considerably and they figure to be more of a trade partner than they would be to sign another big name free agent.

Of course, if they’re one of the teams going to Plan B then lineup the agents outside the Phillies suite and let the negotiating begin. The Phillies would then have money to talk to Kyle Tucker or Cody Bellinger about filling an outfield spot or pivot to Alex Bregman or Pete Alonso, maybe even a Bo Bichette discussion. While Bellinger is a left-handed hitter and the Phillies are already too left-handed in their lineup, he is like Schwarber in that he pounds lefties. Last season, the 30-year-old hit .353 against left-handed pitching compared to .244 against righties. Over his career, the numbers aren’t as dramatic, but he has a split of .267/.257 versus lefties compared to righties.

Pete Alonso would become the Phillies DH with some time at first base to spell Bryce Harper if the Phillies were to go after him. While Alonso has never reached his rookie season high of 53 home runs, he has never hit less than 34 home runs, not counting the COVID shortened 2020 season when he hit 16 in 57 games. Ironically, Alonso turns 31 on Sunday, the day that baseball folks start rolling into Orlando. Where would Bregman play? He has played other positions, but none since 2019 when he played 65 games at shortstop, which the Phillies don’t need. Third base if filled for the time being by Alec Bohm, but the annual chorus of trade rumors is rising up and could be discussed at the Winter Meetings with interested teams. If Bohm were traded then Bregman would take over at third. The other alternative would be DH if Bohm were to stick. Putting Bregman at third to start the 2026 season with Bohm being dealt elsewhere would fit the future plans for the Phillies. One of their top prospects, Aidan Miller, would learn third base at the Triple-A level and when he is ready for his MLB debut, he would simply push Bregman to the DH spot.

Kyle Tucker is the big name after Schwarber, but concerns over his mental makeup and clubhouse popularity – or lack thereof – have made some teams shy away from him. He also is not coming off of his best season offensively, so that will hurt his wallet a little and give some teams further concern for what they would get from him going forward.

This for that

Alec Bohm, Bryson Stott, Brandon Marsh, Matt Strahm, Tanner Banks and certainly Nick Castellanos have all been in trade rumors during the early part of the offseason. The Mariners are in desperate need of relief pitchers and want to add two relievers this offseason with one of them being a left-hander; that’s where Matt Strahm comes in. Of course, Tanner Banks could also be a fit.

Bohm and Castellanos are both free agents after next season, which affects their value and which teams would want them. The Phillies are looking to get Castellanos out of Philadelphia as soon as possible even if it means paying most, or all, of his salary. The fact that the Phillies want to get rid of him so badly that they would consider simply releasing him has some teams thinking they should wait out the Phillies to see if they can get him without having to deal a player.

Stott is still young and under team control. He has taken well to second base after primarily playing shortstop in the minors. As a young, controllable player that gives solid defense up the middle and who scouts believe will get better offensively, teams are certain to have some interest. His value is going to go up though once Bichette decides where he is going and teams pursuing him turn to Plan B.

On Bohm, the Phillies could keep him and hope he gets off to a big start, which would give Miller time to learn third base in the minors. The Phillies would either then have a hot third baseman for the rest of the season or potentially trade him to another contending team at the deadline for another usable piece of their puzzle.

The backstop

Catching is another position of concern for the Phillies. That can be solved easily by re-signing J.T. Realmuto which would cause the pitching staff to celebrate since Realmuto is one of the best game calling and defensive catchers in baseball. If Realmuto goes elsewhere – Boston, Cincinnati, Pittsburgh – then the Phillies have to decide if the Rafael Marchan era begins. Or is it the Garrett Stubbs ear? Probably neither. The Phillies would look to trade for a serviceable catcher to start most of the games this season with either Marchan or Stubbs being the backup and likely called on to play more games than they have played backing up Realmuto. Even if Realmuto returns, the Phillies backup could be called on to play more to give him some extra days off.

The bullpen

The Phillies would like to find another arm to put into the back end of the relief corps. A couple of quality relievers have come off the board already, but there are some free agents still sitting out there. Luke Weaver, who has made 126 relief appearances over the past two seasons with the Yankees would be the primary target. Edwin Diaz, Robert Suarez and Kenley Jansen are also still out there.

The jury is still out on Orion Kerkering. After his costly decision making in the NLDS that led to the Phillies being eliminated from the playoffs, there is some concern over how he would handle coming back to Philadelphia. The players would all welcome him, but his psyche could have taken quite a hit and a change of scenery may be best for the young right-hander. The Phillies front office has likely been in touch with him and would have a better gauge on how he feels about returning next season.

Outfield revamping

Right now, nobody really has an outfield job locked up. Castellanos is gone and the Phillies brass weren’t happy with the production of the outfield last season. Justin Crawford has his name penciled in for either left or center, but he is going to have to change the pencil to pen in Spring Training. Plus, a decision has to be made on which spot he plays. He’s decent in center, but profiles better in left. A lot of that though will be determined by any other moves the Phillies make to add an outfielder. If they find someone they like in center, then Crawford plays left and vice versa.

Don’t count out the return of Harrison Bader to the Phillies. Both sides are interested, but it will likely come down to just what Bader finds on the open market. Teams will look at his 2025 season which was his best offensively and consider the spark he provided for the Phillies and have to decide if it was a breakout season or just a guy putting up huge numbers for a new contract. He loved playing in Philly and was a great clubhouse fit, so a return to Philadelphia makes sense if the price is right.

Does Marsh go back to being a platoon player or do they write him in every day as the right fielder? Johan Rojas is having another strong winter ball season, but does he fit in for the future with the Phillies? He too has been mentioned as a potential trade piece in a package deal with another team.

The Schwarber situation will dictate how a lot of the outfield dilemma is answered. Another option for the Phillies is to re-sign Schwarber and take a long look at Gabriel Rincones Jr. to fill the right field spot in 2026. Rincones, 24, hit a career-high 18 home runs at Triple-A Lehigh Valley last season, but the fact that he hits left-handed may make him a better fit to come off the bench or stay at Triple-A as insurance.

Let’s bottom line this thing

The Phillies are set up to be one of the busiest teams at the Winter Meetings. Certainly they will be doing a lot of talking with other teams and agents for players on the open market. Can they push something – Schwarber for instance – across the finish line? The odds are good. If they were to shake up an old Magic Eight Ball, the answer would come up: “Outlook Good.”