3 colossal questions facing the Phillies as the offseason officially begins

It feels like the Philadelphia Phillies’ offseason has already been dragging since their earlier-than-expected exit from the MLB playoffs. But now, the offseason has officially begun with the Phillies-less World Series wrapped up and the Los Angeles Dodgers taking the 2024 crown.

As we dive into the next three and a half months without any major league baseball, here are three huge questions we’ll be thinking about until there’s some resolution this winter. President of baseball operations Dave Dombrowski and general manager Sam Fuld have their work cut out for them in their quest to help their roster return to the World Series after a pair of less-than-encouraging postseason exits.

Who will be playing outfield for the Phillies in 2025?

The Phillies’ outfield was a real mess this past season, at least from an offensive perspective. Nick Castellanos played all 162 games in right field, and put together a solid season after a glacial-like start. Other than that, the outfield was a massive source of angst for fans, and likely the coaches and front office.

The list of things that went awry is so bad that it’s almost comical.

Johan Rojas didn’t turn into an everyday center fielder like the team had hoped he would. Brandon Marsh struggled to gain any traction against left-handed pitching. Free agent signing Whit Merrifield couldn’t hit during his three-and-a-half-month tenure. Trade deadline acquisition Austin Hays couldn’t stay healthy and was a non-factor down the stretch and into the playoffs.

The Phillies find themselves in a real pickle this offseason. With the personnel they currently have, left and center field are huge question marks for 2025. Dombrowski has given himself plenty of wiggle room for the outfield to look different next year, giving Marsh and Castellanos a vote of confidence after the season. That leaves Rojas and Hays blowing in the wind.

The Phillies can either go out and get a proven difference-maker via trade or free agency (ahem, Juan Soto) who will be guaranteed to fill a spot, or continue the piecemeal operation and hope that No. 3 prospect Justin Crawford progresses to the point of becoming a viable option next year. For a team with World Series ambitions, that latter scenario doesn’t seem like a realistic option on which to rely.

Who will be pitching at the back of the Phillies bullpen in 2025?

There’s a chance that the back end of the Phillies bullpen could look drastically different in 2025, with both Jeff Hoffman and Carlos Estévez heading into free agency.

Dombrowski has said that he’d like to sign one of these free agent relievers, but it’s highly unlikely that both Hoffman and Estévez are back in red pinstripes next season. Hopefully, the Phillies can bring one back, but who that will be is anyone’s guess. Hoffman seems like the most likely candidate based on his projected costs, familiarity with the club, and his comments in the latter stages of the season.

They still have Matt Strahm, José Alvarado, Orion Kerkering, Tanner Banks and José Ruiz to fill out the bulk of the relief corps. Adding another two high-leverage arms has to be a priority this offseason, especially with how the bullpen imploded in the playoffs. Standing pat won’t be good enough.

Even if they bring back Hoffman, they’ll still need to scour the free agent pool for another reliable arm. Luckily, there’s a long list of free agent relief pitchers heading to the market this winter. With names like Tanner Scott, Clay Holmes, Paul Sewald and Blake Treinen available, there will be plenty of options for the Phillies to pursue.

How serious will the Phillies’ be about pursuing Juan Soto?

And finally, the biggest question of the MLB offseason: Where will Juan Soto sign as a free agent?

The Phillies have been included in the short list of teams the insiders and experts believe will take a run at this winter’s top free agent. They’re up against the New York Yankees, New York Mets, Toronto Blue Jays, San Francisco Giants and perhaps the Los Angeles Dodgers, just to name a few. Those are the teams we’ve been hearing about for months now.

Sure, the Phillies will make a play for Soto. They’d be silly not to. But how seriously will they take the pursuit? Will managing partner John Middleton give Dombrowski the go-ahead to write Soto a blank check? As unlikely as that seemed after Dombrowski’s comments during his end-of-season press conference, a recent tidbit of news made it seem entirely possible.

According to The Philadelphia Inquirer’s Scott Lauber, Middleton is open to pushing the Phillies’ payroll past the third tax threshold, for the right player (subscription required).

“For the right player, I have a high degree of confidence that Dave and I would go over the third limit,” Middleton said, per Lauber.

Dombrowski didn’t rule out a serious Soto chase, and Middleton wants his bleeping trophy back, so there’s still hope. But with a handful of serious contenders with deep pockets, Phillies fans might not want to hold their breath waiting for what would be a monumental free agent signing.