It’s an antsy time of year on the baseball calendar. Teams are either “in on,” “interested in,” or “heavily interested in” a variety of top-tier free agents and trade targets. They’re also speaking with agents, gauging the market, parsing their rosters for possibilities and potential. It’s hard to know which fires are real with so much smoke, leading to both wild speculation and muted expectations. 

One thing is for sure: the Phillies will have another busy offseason. After its World Series defeat last year, the team had direct targets on a couple big names and went after them immediately. In the week following the Winter Meetings, the Phillies signed Trea Turner, locked up lefty reliever Matt Strahm, and then solidified their back-end rotation needs with Taijuan Walker. In the span of eight days, president of baseball operations Dave Dombrowski crossed off his major to-do list with a trio of heavy expenditures. 

This offseason is a little trickier. 

While the Phillies mostly bring back the entirety of last year’s lineup, they share a few areas of need with a variety of other teams. The biggest items on their wish-list? A top-tier starter, especially after Aaron Nola officially rejected the team’s qualifying offer this week to explore the open market. Then there’s the outfield. Earlier this month, Bryce Harper made it clear he’d like to play full-time at first base moving forward, meaning a reunion with Rhys Hoskins is unlikely. With his move to the infield, and after Johan Rojas’s struggles with the bat throughout the postseason, the Phillies could use some more right-handed pop to complement Marsh and Castellanos. And then there’s the bench, which might require turnover after a second-half that saw little production from Garrett Stubbs, Edmundo Sosa, Rodolfo Castro, and Jake Cave. 

In other words, there are plenty of opportunities to tinker and improve, plenty of players hoping to bring in big paydays, and plenty of trade candidates that won’t come cheaply. Money, however, shouldn’t be a huge concern for the Phillies, even after exceeding the luxury tax threshold last year. “I’ve talked preliminarily with John… I would be surprised if we don’t have the finances to support what we need to do,” Dombrowski said at his end-of-year press conference. 

That’s always a positive thing to hear. Ahead of this year’s Winter Meetings, which take place in Nashville between Dec. 4 and Dec. 6, here’s a look at the biggest questions Dombrowski and the front office will be looking to answer. 

What starting pitcher—or pitchers—will the Phillies end up with? 

The wave of speculation surrounding the Phillies’ No. 2 starter vacancy has already been a bit of a roller-coaster. In an ideal situation, the team brings back Nola, its home-grown workhorse, who, despite a rocky regular season in 2023, stepped up his efforts in the postseason and showed extended flashes of his dominant self. The truth is, he seems like the Phillies’ best option to continue their reign in the National League and maintain the continuity of a still formidable rotation (Wheeler, Suarez, Walker, Sanchez) that suffered some setbacks at the beginning of last season thanks in part to the World Baseball Classic. If he doesn’t return, however, there’s a few other intriguing options.

– Blake Snell: The lefty won the National League’s Cy Young Award this week, but the red flags surrounding him mostly boil down to his workload. Snell pitched 180 innings in 2023, his highest number of innings pitched by a good margin since 2018. And yet, over the last eight years, Nola has thrown about 350 more innings than him. 

– Yoshinobu Yamamoto: The Japanese ace is only 25 years old and seems to be a legit workhorse, with scouts saying he’s much better than Kodai Senga was last year. This might be the most expensive starter on the market—especially with the posting fee attached—but if the Phillies do move on from Nola, he’d likely be the next best option. The Phillies has been linked to him—along with several other high-profile teams. 

– Dylan Cease/Corbin Burnes: Both starters would fulfill what the Phillies are looking for behind Zack Wheeler, but both would also need to be acquired via trade. This might include a package that involves Mick Abel, the team’s next best starting pitching prospect after Andrew Painter, who isn’t likely to pitch in 2024. It might also require first-round pick Aidan Miller. The question for the Phillies is whether it will be worth parting with valuable prospects for a pitcher that equates to Nola’s output. 

Will the Phillies upgrade the bullpen with a veteran closer?

Last week, Fox’s Jon Morosi reported the Phillies and Rangers were “top of the list” for lefty closer Josh Hader. 

Over the last few years, the team has attempted to fill the ninth-inning role by throwing one-year deals at veterans or acquiring them through trades—think Corey Knebel, David Robertson, and Craig Kimbrel. But in that time, the Phillies bullpen has gained some valuable postseason experience and developed a few promising in-house candidates able to compete in high-leverage situations. Jose Alvarado, Seranthony Dominguez, Jeff Hoffman, Gregory Soto, and Matt Strahm are all under control for 2024. That doesn’t even mention a few other youngsters and 40-man roster players: Orion Kerkering, Connor Brogdon, Yunior Marte, and Andrew Baker. 

While the Phillies should still enhance the bullpen with another solid arm or two, Hader would come at a hefty price. And understandably so. He’s racked up at least 33 saves over the last three seasons and finished last year with a 1.28 ERA. Still, the team’s offseason spending seems better suited for a starter and outfielder than on a role that can already be seen as a considerable strength. If anything, a veteran closer might be a better option at the trade deadline, should injuries or unset roles be an issue. 

Is Mike Trout in this team’s future? 

Over the last several years — well, really ever since Bryce Harper signed with the Phillies and began campaigning for other big-name players to join him — Mike Trout has been linked to Philadelphia. The Jersey native has been a frequent attendee at Eagles games and the match makes a ton of sense. At this point in his career, the question around Trout, 32, is whether one of the best players in the league can put together a healthy season after being marred with multiple injuries last year. 

The other question would be how much the Angels would demand from the Phillies in a trade. In addition to Abel and Miller, there’s Griff McGarry, another promising starter, along with outfielder Justin Crawford who teams will likely ask for. In some ways, Trout on the Phillies makes a ton of sense, filling both a need and a place in so many fans’ hearts. But, past his best healthy days, does ge warrant leveraging a chunk of the farm? I wouldn’t bet on a big deal happening. 

What outfielders and bench players might the Phillies acquire? 

In an ideal scenario, Rojas fine-tunes his swing over the spring, gains a little more pop, and becomes the long-term, Gold Glove center fielder the team has lacked for the last decade. In a more realistic scenario, Rojas makes some strides at the plate, but not fast enough to rely on him for an entire season—and especially not as the everyday nine-hitter in the playoffs. 

As a result, the Phillies should be in the market for a corner outfielder, potentially leaning on a platoon involving Marsh and Pache in center field. 

The Phillies defense markedly improved when Kyle Schwarber permanently moved to the DH role midway through the season, though with Harper at first base, it’s not unreasonable that Schwarber will get an occasional start in the outfield to give Castellanos or Realmuto a day off from the field. Though they’d love some equivalent power, it seems like the Phillies would be OK sacrificing it for a reliable left fielder that can provide more of a threat at the plate than Rojas—and ideally won who doesn’t chase as much as Castellanos. 

There are a few right-handed bats out there that would seem to fit the Phillies, such as Jorge Soler, Adam Duvall, and Tommy Pham. And then there are a handful of minor-league players who will jockey for playing time and a role on the bench, specifically utility player Weston Wilson, who might steal a spot away from Pache or Sosa considering the limited amount of options each of them has remaining. Wherever Cody Bellinger goes and however much he signs for could go a long way in setting the market for corner outfielders and other role players. 

Will anything crazy happen? 

Never say never. 

In recent weeks, there was some early chatter about the Phillies trading away Castellanos that was then quickly shut down. In other corners, there’s still rumblings that the Padres could be influenced to move Juan Soto, who would seem like a good candidate to take over in left field. 

Still, based on the way Dombrowski has talked about the core he’s returning in 2024, it doesn’t seem likely that he’ll do anything crazy. The Phillies still have a loaded roster with lots of players locked up in the middle of their primes. It makes more sense for this team to add through spending than by shaking up the formula that’s gotten them to the NLCS in consecutive years.