As another postseason unfolds, we’ve been privy to yet another premature October exit from the Phillies. The competitive window that began as a Cinderella run in 2022 has quickly soured into four straight years of disappointment for a fan base in desperate search of a ring.

President of Baseball Operations Dave Dombrowski has made a series of big-money, win-now moves in an effort to get his club across the finish line, which have yielded diminishing results year over year.

It's fair to wonder whether they've reached the end of the line with their current core. They have loads of money on the books and a less-than-inspiring farm system.

Or, can they reconfigure their roster to finally capture an elusive championship? Let’s fire up the BTV trade simulator and find out. 

First and foremost, let’s get the money out of the way. The Phillies’ 2025 payroll weighed in at a hefty $291 million, according to Fangraphs, fourth-highest in all of baseball. That put the team well over MLB’s $241 million luxury tax threshold, and they look set to blow past that barrier once again in 2026. Just how far owner John Middleton is willing to go, however, isn’t clear.

There is some salary relief on the horizon, as stars J.T. Realmuto, Ranger Suárez and Kyle Schwarber, as well as role players Max Kepler, Jordan Romano, Harrison Bader, David Robertson, and Joe Ross are all coming off the books. Some of those are easy decisions to let walk, but others, like Schwarber, Realmuto and Bader, will leave craterous holes to fill. If Dombrowski doesn’t want his squad to take a step back in 2026, he’ll most likely need to spend some more money or prospect capital just to plug those gaps.

The current iteration of the Phillies has lived up to Middleton’s promise to spend “stupid money,” but there’s always a line somewhere, and it’s quite likely Dombrowski would prefer most of the players he reels in via trade to not break the bank. Now, with all this in mind, let’s group together the Phillies’ potential trade pieces and see what can be done.

 

Albatross Contracts (Probably Untradeable)

Part of what has led to the club’s sky-high payroll are some ill-advised contracts that were given out to bolster their World Series hopes. Two notable anchors are Nick Castellanos (five years, $100 million) and Taijuan Walker (four years, $72 million) both of whom are in the final year of their pacts, and have greatly underperformed expectations. Castellanos in particular has been embroiled in a well-publicized feud with Manager Rob Thomson over his demotion to part-time playing duties. In short, both players could use a change of scenery, and the Phils would love to clear at least some of their guaranteed money off the books.

Neither player will be easy to move, as our model has Castellanos completely underwater at -$20 million in surplus value, and Walker at just a tick above a total loss at -$16.6M. If the Phillies are serious about trading either one, they’ll need to eat most or all of the remaining money, take on another bad contract, or attach prospects to get someone to bite.

On a similar note is former All-Star Aaron Nola, the longest-tenured Phillie of them all. The 2014 first-rounder was one of the few success stories from a dismal decade-long rebuild in Philadelphia, and re-upped with the team two offseasons ago on a seven-year, $172 million deal.

Unfortunately, after a solid first season of that contract, Nola had a 2025 to forget, missing half the season due to ankle and rib injuries, and posting a ghastly 6.01 ERA over the 17 starts he did make. Now 32 years old with declining velocity, Nola’s borderline ace days may be over. With so much money left to be paid out over five more years, his surplus value is negative in our model (-$50.6 million), so it’s hard to see another team letting the Phillies off the hook for this one.

 

Trade Proposals

Here's one option:

 

Marlins get:		Phillies get:
Castellanos	-20	Tarnok	0
Cash	16
Total	-4	Total	0

 

It seems Castellanos is as good as gone from the Phillies, with multiple reports suggesting the two-time All-Star’s relationship with the coaching staff and front office is fractured beyond repair. There’s a decent chance the Phillies release him outright and eat the remaining $20 million owed to him, but they’ll undoubtedly look to get out from under as much of that money as they can. It’s possible a team lacking in offense and star power could bring in the beleaguered veteran and hope to turn him around for a nominal price.

The Marlins looked plucky and exciting for stretches of 2025, but ultimately fell short of a .500 record in Manager Clayton McCullough’s first season at the helm. A roster teeming with young talent might benefit from the addition of a decorated veteran to a mediocre outfield mix and heart of the order.

This scenario has the Phils retaining $16 million of Castellanos’ salary, netting $4 million in savings while receiving nothing more than a warm body in post-hype reliever Freddy Tarnok. With the Phillies needing to splash some cash in order to re-sign or replace core pieces, every little bit of breathing room helps.

 

Angels get:		Phillies get:
Walker	-16.6	Stephenson	-9.2
Rojas	6.6
Total	-10	Total	0

 

Walker has been one of the more reviled free agent busts of this Phillies era, as he’s posted an ugly 4.88 era in three seasons with the team. The former All-Star’s best days are clearly behind him, but he did bounce back from an atrocious 2024 season with 123.2 innings of 4.08 ERA ball as a swingman this past year. Walker’s goodwill ran out a while back in Philadelphia, but a team in need of an innings eater could take on the last year of his contract. 

Enter the Angels, whose playoff drought has now reached 11 seasons, and had only one starting pitcher with a sub-4.00 ERA last season. They’d be doing the Phillies a favor by getting Walker’s $18 million off the books, so they could even the scales by shedding tantalizing, but oft-injured reliever Robert Stephenson’s $11 million salary, and bringing in centerfielder Johan Rojas. His bat hasn’t played in the majors, but his Gold Glove-caliber defense and elite speed do hold value.

This deal isn’t a significant needle mover for either side, but it does give the Phillies an extra $7 million to work with this winter, while adding a reliever who could take down meaningful innings for the team if he can get healthy. For the Halos, they’ll add an experienced starter to take the ball every fifth day, and a young centerfielder with a few elite tools.

 

Major League Contributors (Possible Trade Chips)

With the prospect cupboard relatively bare, Dombrowski may need to start subtracting from the major league roster in order to reel in impact players. It’s not something a contending team wants to do, but with the Phillies’ championship window closing ever further shut, changes may need to be made. 

Of particular interest to other teams would be a pair of young hitters in Bryson Stott (who we have at $30.4 million in surplus value) and Brandon Marsh ($28.5M). Both lefty swingers are heading into their age-28 season with two years remaining of club control. Marsh has been miscast as an everyday centerfielder, but the July acquisition of Harrison Bader allowed him to shift into a corner outfield role to which he is much better suited. As a solid defender in left who mashes right-handers, Marsh would hold a good deal of value if made available.

Stott is closer to the inverse of Marsh, as his contact-oriented approach has yet to make him even a league-average hitter, but his spectacular baserunning and second-base defense make him a productive big league regular nonetheless. The Phillies would certainly love to hang on to Stott and coax a bit more out of his bat, but if a deal can be made to improve the current roster it needs to be considered.

In a different boat is 24-year-old reliever Orion Kerkering ($21.6M), a fire-balling righty who has four more years of club control. Billed as a future lockdown closer, Kerkering has used a wipeout sweeper and triple-digits heater to great effect in his two full major league seasons. Unfortunately, his Bill Buckner-level fielding gaffe ended the Phillies’ 2025 postseason, and the ensuing firestorm has led many to question whether Kerkering will ever be able to reach his full potential in the City of Brotherly Love. If management does decide it’s best for everyone to move on, there should be no shortage of clubs looking to add a dynamic arm to the back end of their bullpen.

Last but not least is mercurial third baseman Alec Bohm ($5.4M). The 2018 third overall pick has had a bumpy Phillies tenure thus far, looking like a high-average extra base hit machine at his best, and a granite glove singles hitter at his worst. The true Bohm is probably somewhere in between, but with only one year left of team control the Phillies may not want to find out which Bohm they’ll get in 2026. It was reported that the club was aggressively shopping him last offseason, and with fans clamoring for significant changes to the lineup after another playoff debacle those trade conversations are sure to pick up again. Bohm won’t return a major haul, but a decent hitter who has improved his defense could bring back something useful from a team in search of answers at the hot corner. Dombrowski may opt to ship him out in exchange for help at another position, and chase a big name free agent like Alex Bregman.

 

Tigers get:		Phillies get:
Stott	30.4	Vest	19.9
Fisher	3.3	Carpenter	14.8
Total	33.7	Total	34.7

 

The Tigers got a solid year out of free agent acquisition Gleyber Torres, but are set to have a hole at second base with the former Yankee returning to the open market this winter. Stott would fit their club perfectly as a contact-first hitter with great fundamentals. 

Detroit’s strengths line up well with the Phillies’ weaknesses, as a crowded outfield picture has led to sweet-swinging Kerry Carpenter receiving only part-time duty thus far in his big league career. The corner outfielder has more than made up for a mediocre glove with a terrific .828 OPS in his four major league campaigns, and is arbitration eligible for three more seasons.

Rounding out the package for Philadelphia is right-handed closer Will Vest, a 30-year-old with two more years of club control. Vest racked up 23 saves for the Tigers this past season en route to a 3.01 ERA. That was his third straight season of well-above-average work, and his addition would make for a dynamic one-two punch with Jhoan Duran at the back end of a shaky Phillies’ pen.

Bridging the gap between the two sides is recent Phillies draftee Matthew Fisher, a 19-year-old righty who was given almost five times his slot value to sign with the team. Fisher has yet to debut in pro ball, but the going theory is that four quality offerings could make him a future mid-rotation starter in the big leagues.

 

Mariners get:		Phillies get:
Bohm	5.4	Ford	12.5
Heredia	6.5
Total	12.1	Total	12.5

 

The Phillies and Mariners were linked in Bohm trade rumors last winter, and Seattle’s need at the hot corner isn’t going away with trade deadline acquisition Eugenio Suárez hitting free agency in a matter of days.

As luck would have it, the M’s have a glut at another position that could help Philadelphia immensely, as top-100 prospect Harry Ford is blocked behind the plate by MVP favorite Cal Raleigh. The Phillies traded away their top catching prospect, Eduardo Tait, in the Jhoan Duran deal this past summer, and incumbent J.T. Realmuto is about to hit free agency. Ford got a taste of the majors in 2025, and could be the long-term answer for Philly moving forward.

One year of Bohm at a salary in the $10 million range is certainly not equal to six years of an elite catching prospect, so Dombrowski can sweeten the pot with 21-year-old outfielder Raylin Heredia. The Dominican posted a rock solid .809 OPS at High-A this past year, but doesn’t quite fit the timeline of a win-now Phillies club.

 

Cubs get:		Phillies get:
Kerkering	21.6	Happ	5.2
Castellano	1.6	Amaya	8
		Cash	10
Total	23.2	Total	23.2

 

The Cubs have a panoply of outfielders in established stars Ian Happ and Seiya Suzuki, breakout sophomore Pete Crow-Armstrong, and intriguing prospects Owen Caissie, Kevin Alcántara and Kane Kepley. A porous bullpen was the club’s achilles heel all year, which is why they might have interest in Kerkering.

The Phils and Cubs line up almost perfectly, as Kerkering would do wonders for an ailing Cubs pen, while Gold Glover Happ would plug right into a Phillies outfield that has uncertainty at all three spots. A free agent after 2026, Happ would bring a solid bat to the middle of the Phillies’ lineup, while his departure would free up playing time for some of Chicago’s young talent.

To even things out the Cubs would need to cover about half of Happ’s salary, and tack on catcher Miguel Amaya, a once-promising prospect who has yet to establish himself in parts of three big league seasons. Amaya has some bust potential, but the Phillies would love to take a chance on him given the dearth of backstop talent in their farm system. Lastly, Philadelphia gives up Eiberson Castellano, a 24-year-old starter who followed up a breakout 2024 campaign with an injury-riddled 2025.

 

Guardians get:		Phillies get:
Marsh	28.5	Gaddis	17.8
		Sabrowski	6
		Watson	3.8
Total	28.5	Total	27.6

 

The Guardians rode an unbelievable pitching staff to a miraculous division title this past year, but the offense that barely got them by in the regular season proved to be their undoing in October. As a result, the club could subtract from its dynamite bullpen in order to bring in some more firepower. 

Marsh is clearly better suited to a corner outfield role, which he could play in Cleveland. The Phillies don’t currently have a Marsh replacement waiting in the wings, but in order to upgrade an aging core they may need to consider wheeling and dealing to bring in different outfield options while improving other parts of the roster.

Hunter Gaddis and Erik Sabrowski are two 27-year-old relievers who have done yeoman’s work in the Cleveland pen. The right-handed Gaddis has a longer track record with four big league seasons under his belt, while the southpaw Sabrowski is a late bloomer who put himself on the map with a sub-2.00 ERA in 2025. Gaddis can be controlled for four more seasons and Sabrowski for five.

Finishing off the package for Philadelphia is 2021 first-rounder Kahlil Watson, a shortstop-turned-outfielder whose attitude issues put his career in jeopardy a few years back, but rebounded after a change of scenery to post a marvelous .813 OPS in the high minors this past year.

 

Prospects of Note (Possible Trade Chips)

The Phillies organization has never been known for its ability to develop homegrown players, and while the current regime has made some strides in that department the club is still far from awash with young talent. However, Dombrowski and company do seem to have scored with three recent first round picks in Andrew Painter ($40.8m in surplus value), Aidan Miller ($33.7M) and Justin Crawford ($18.4M).

Painter, a Florida high school pitcher who was taken 13th overall in 2021, is the biggest prize of the bunch. He decimated older competition in his first few minor league seasons, and quickly rose up prospect boards to a top-20 ranking. Unfortunately, Tommy John surgery wiped out the entirety of his 2024, and he looked mortal in his first taste of Triple-A in 2025. The 22-year-old still has a legitimate chance at becoming an ace, but with his value dinged a bit after a rough year, it’s doubtful the Phillies would trade him at this time.

Shortstop Miller was dogged by injury concerns during the 2023 draft, allowing the Phillies to steal him late in the first round. The 21-year-old has raked in his three minor league seasons, and has thus far fended off concerns about moving down the defensive spectrum. A consensus top-50 prospect, Miller is capable of headlining a trade return for just about anyone in baseball.

Speedy outfielder Crawford was selected 17th overall back in 2o22, and has so far shown a very similar skillset to his father, Tampa Bay Rays great Carl Crawford. The 21-year-old makes up for below-average power with a tremendous hit tool, posting a .322 batting average over four minor league seasons and an even better .334 mark in Triple-A this past year. He’s not quite on the level of Painter or Miller, but Crawford should have plenty of value if the Phillies make him available in trade talks.

 

Tigers get:		Phillies get:
Miller	33.7	Skubal	51.6
Crawford	18.4
Escobar	9.1
Total	61.2	Total	51.6

 

Let’s get crazy here. The Phillies’ clear strength is their starting pitching, with Cristopher Sánchez cementing his status as a top-ten pitcher in baseball, Jesús Luzardo looking downright unhittable for prolonged stretches, longtime ace Zack Wheeler set to return from injury over the summer, and Painter on the cusp of his major league debut. The Phillies don’t necessarily need another starter, but one way to drastically improve a flawed roster is to acquire the best pitcher on the planet, and that man is Tarik Skubal.

The soon-to-be two-time Cy Young Award winner will reach free agency after the 2026 season, and should be in line for a record-setting payday. Unfortunately, his camp and the Tigers are worlds apart in negotiating an extension, and rumors persist that he could be made available this winter.

It won’t be easy to pry the best in the world loose, but the Phillies could give it a good shot by offering up two of their three best prospects. Painter is likely off limits, but a package of Miller and Crawford could pique Detroit’s interest, and if the Phils are willing to overpay with another well-regarded youngster like second baseman Aroon Escobar, who saw his stock rise considerably with an .828 OPS in low-A,they just might be able to get a deal done.

It would take a lot of guts to stripmine the team’s farm system for a one-year gamble in Skubal, but Dombrowski has pulled off stunners like this in the past. Such a deal would leave the Phillies’ future in a precarious spot moving forward, but flags fly forever and there are few moves that could have the same impact on the team’s chances of winning a title with this core.

 

Conclusion

The Phillies have been one of the best teams in baseball for almost half a decade, and should remain so in 2026. However, their stars are another year older and they have some major flaws that need to be addressed. The club hasn’t been able to get over the hump in four consecutive playoff appearances, and running it back yet again would have fans on the verge of rioting.

A desire for positive change doesn’t always line up neatly with the ability to change, and the Phillies seem somewhat boxed in right now. Their payroll is at or near the highest it can go, and the farm system doesn’t have enough quality prospects to make multiple sweeping changes. 

As a result, the Phils will either need to spend above and beyond 2025 levels, deal away the handful of solid prospects they do have, or start cutting into the bone of the major league team. None of those options paint a particularly rosy long-term picture, but the window to win a World Series is open right now, and closing with each passing season. A successful October run will make it all worthwhile, but in order to get there the Phillies are going to need to take some serious risks.