To this point in their competitive window the Philadelphia Phillies have been extremely hesitant to trade from the highest echelon of their farm system, clinging tightly to top prospects Andrew Painter, Aidan Miller, and Justin Crawford in negotiations. Phillies president of baseball operations Dave Dombrowski has made clear his desire to keep all three youngsters, but the veteran shot caller has made earth-shattering deals in the past and perhaps could be swayed for the right player.
Trading away their best prospects might be the only way to put the Phillies over the top. Let’s jump into some potential packages that could convince Dombrowski to clear out the team’s farm system in an effort to make good on the current championship window.
One quick note: all of these trades would be mutually exclusive for two reasons. First, the Phillies would only need to address a position once, so trading for a centerfielder in Luis Robert Jr. would make another deal for Byron Buxton redundant, a catcher like Kyle Teel would box out Ryan Jeffers, so on and so forth.
Secondly, the Phillies’ farm system is far from deep, and the team lacks the necessary depth to pull off multiple impact trades. If even two notable youngsters are shipped out it’ll leave the club without enough ammo to pull off another stunner. Think of each of these deals in a vacuum, not all in the same timeline.
With that in mind, on to the trades.
7 trades the Phillies should sell the farm for to win the World Series
1. Kyle Teel and Luis Robert Jr., CWS
Twenty-three-year-old catcher Kyle Teel landed with the Chicago White Sox only one year ago as the main piece in the Southsiders’ blockbuster trade of ace Garrett Crochet to the Boston Red Sox. The New Jersey native put up an excellent .273/.375/.411 line in his rookie season and is looking every bit like the future star he’s been billed as.
However, Chicago has another tantalizing young backstop in Edgar Quero, and the team has reportedly been receiving interest in both catchers. It wouldn’t be ridiculous for general manager Chris Getz to consider trading away one of the two in exchange for a package of prospects at other positions.
White Sox center fielder Luis Robert Jr. has been the subject of trade speculation for years now, as the mercurial Cuban has shown flashes of elite play interspersed with long bench-worthy stretches. No team has met Chicago’s high asking price yet, but given the fact that the 28-year-old is in his last season of team control it may be best to ship him out now as part of a larger package.
Both Teel and Robert would fill holes in the Phillies’ lineup, as center field is projected to be filled by rookie Justin Crawford and longtime catcher J.T. Realmuto has yet to make a decision in free agency.
The White Sox won’t let go of two of their best players for cheap, but a package of slugging second baseman Aroon Escobar, flamethrowing right-hander Moisés Chace and powerful outfielder Raylin Heredia may be enough to loosen their grip. To balance the scales a bit, the Phillies could get the Sox to retain half of Robert’s $20 million salary for the coming season.
2. Byron Buxton and Ryan Jeffers, MIN
Superstar center fielder Byron Buxton was the last man standing in Minnesota last summer, as the Twins tore things down to the studs, trading away virtually any major leaguer with value. The two-time All-Star decided against waiving his no-trade clause at the time, but after seeing the dumpster fire Minnesota has become he may acquiesce this time around.
As a Platinum Glove Award winner who posted a .264/.327/.551 line last season, a five-tool talent like Buxton would solve the Phillies’ perennial center field problem for the next three seasons.
Another asset the Twins should be looking to cash in on is catcher Ryan Jeffers who’s entering his final year of club control.
The North Carolinian broke out in a big way with an excellent .858 OPS in 2023. He hasn’t quite reached that level since but has remained a perfectly acceptable everyday backstop. Bringing in the 28-year-old would allow the Phillies to avoid committing a good deal of money to an aging Realmuto while getting similarly solid production behind the plate.
Twins president of baseball operations Derek Falvey could hold Dombrowski’s feet to the fire with this one, extracting a package of Justin Crawford, Chace, switch-hitting catcher Rafael Marchán and intriguing right-hander Jean Cabrera. To ease the Phillies’ pain just a bit the Twins could kick in veteran reliever Justin Topa, a 34-year-old on an expiring deal who would add another solid right-handed look to the bullpen.
3. Brendan Donovan and OF Lars Nootbaar, STL
Second base has been a haven for fan favorites in Phillies history, as franchise greats like Juan Samuel, Mickey Morandini and Chase Utley have manned the keystone. Lovable Jean Segura held it down during the team’s 2022 pennant run, and was replaced by first-round pick Bryson Stott in the ensuing years.
Stott has made a name for himself with elite glovework and terrific baserunning, but unfortunately his bat has yet to live up to the hype he came to the majors with. Fans would be loath to see Stott supplanted, but second is a position that could be improved upon in 2026.
To do so Dombrowski should reach out to the St. Louis Cardinals, inquiring about All-Star Brendan Donovan. The utilityman has bounced all over the diamond, providing impeccable defense with a well-above-average bat. The 28-year-old earned his first Gold Glove Award this past season and has appeared in more games at the keystone than any other position. Donovan would not only be a massive upgrade offensively, but would provide just as much defensive value to the Phils as Stott.
Dombrowski should look to land outfielder Lars Nootbaar alongside Donovan in an effort to bolster an outfield group that has failed to produce for multiple years now. A Brandon Marsh-esque player, Nootbaar mashes righties, but doesn’t have quite the same struggles against southpaws as Marsh. Nootbaar is fully capable of manning all three outfield positions, and the Team Japan star would add a solid lefty bat to the middle of the Phillies’ order.
Seeing as both Donovan and Nootbaar have two years of control remaining, it would take quite a haul to pry them loose from the Cardinals. A deal would have to start with Stott, a ready-made replacement for Donovan at second base.
From there Dombrowski could offer up 2024 first-rounder Dante Nori, a fleet-footed centerfielder who made it all the way to Double-A in 2025. Defensive wizard Johan Rojas may have worn out his welcome in Philadelphia, but he should have value to the Cardinals as a spectacular fielder who they can attempt to fix at the plate. Rounding things out are mashing right fielder Gabriel Rincones Jr. and fireballing right-hander Alex McFarlane.
4. Steven Kwan and Hunter Gaddis, CLE
Marsh looks set to be the only returning Phillies outfielder in 2026, but what if that could change? Marsh has done yeoman’s work in his four seasons in Philly, but severe platoon splits and shaky defense in center confine him to part-time duty in left field.
If Dombrowski wants to further upgrade the corners after signing Adolis García, he could seek to acquire hitting machine Steven Kwan from the Guardians.
The 28-year-old Kwan has shown elite contact skills in his four major league seasons, posting a .281/.351/.390 slash line across 2,589 career plate appearances. The Guardians were reportedly asking for Andrew Painter in a Kwan trade at last season’s trade deadline, but after a year in which Kwan’s batting average dropped twenty points perhaps now would be a good time to circle back at a lower price.
The two-time All-Star still won’t be cheap, but a package starting with Marsh and Escobar should be enough to get Cleveland’s attention.
If Dombrowski sweetens the pot with 19-year-old hurler Matthew Fisher and lightning-quick infielder/outfielder Devin Saltiban they could get a deal across the finish line. To make things a bit more palatable for the Phillies, Cleveland could throw in dependable righty reliever Hunter Gaddis who has four more years of team control.
5. Ketel Marte, ARI
Perennial All-Star Ketel Marte has been in the rumor mill recently, as a rift between him and Arizona Diamondbacks management could lead to an unceremonious exit from the desert. Just because Marte is unhappy doesn’t mean the Snakes will give him up for anything less than a king’s ransom, but in order to acquire a true superstar the Phillies just may be willing to meet that asking price.
As was the case with a theoretical Donovan deal, a Marte trade package would need to begin with Stott’s inclusion to fill the hole Arizona would be opening up at second base. Alongside Stott would go reliever Orion Kerkering, who has electric stuff but may be best suited for a change of scenery in the wake of his season-ending error this past October. Joining those two are Crawford and Chace, making this a true farm-clearing trade for the Phillies.
While Painter and Miller may not be part of this package, surrendering three major league-ready pieces and another with top-of-the-rotation upside would wipe out pretty much the rest of the team’s short-term depth outside their top two prospects. However, that price might just be worth it if Marte can put this team’s offense over the top in their pursuit of a championship.
6. Tarik Skubal, DET
A farm-system clearing trades exercise just wouldn’t be complete without a deal that says goodbye to Andrew Painter, the Phillies’ 2021 first-round pick who they’ve clutched with diamond hands for the past four years. Still only 22 years old, Painter has true ace upside and if everything breaks right could blossom into a Cy Young-caliber pitcher in the next few seasons.
However, Painter was banged around to the tune of a 5.40 ERA in his first taste of Triple-A action last season, and he may not be quite ready to take down a full major league workload in 2026. For a team with a shrinking championship window, there may not be time to wait.
The Phillies’ rotation is already a strength with Zack Wheeler and Cristopher Sánchez at the top, electric Jesús Luzardo having proved his grit in last year’s playoffs, and veterans Aaron Nola and Taijuan Walker looking to chew through innings. There are cracks in the armor though, as Wheeler’s recovery timeline from thoracic outlet decompression surgery is up in the air, Nola is coming off a lost season, Walker has never lived up to his hefty contract and Painter might not be big league ready.
One way to ensure the rotation stays the best in the league is to bring in reigning back-to-back Cy Young Award winner Tarik Skubal.
The 29-year-old Skubal has been among the game’s elite for the past four seasons, but went nuclear in the past two working to a 2.30 ERA and racking up 469 strikeouts in that time. In a confusing twist, a competitive Detroit Tigers team is reportedly listening to offers on their prized left-hander, as he should command a record-setting payday in free agency next winter and the Tigers are unlikely to be the ones cutting that check.
It would certainly be painful for the Phillies to cough up Painter, but reeling in the best pitcher in the American League would do wonders for the team’s World Series hopes. Painter alone isn’t enough to acquire Skubal’s services, even for one year, but pairing him with another top prospect in Justin Crawford might get the Tigers to pull the trigger. Given that the Phils would be parting with two of their top three prospects, it wouldn’t be outlandish to ask the Tigers to tack on Kerry Carpenter, a young outfielder who mashes right-handed pitching and has three years of control remaining.
7. Paul Skenes, PIT
Since we've already ventured into the unlikely with a Phillies offer for Skubal, let’s dive all the way into fantasyland and come up with a blockbuster for ace of aces Paul Skenes. The 2023 first overall pick is probably the most valuable single player in all of baseball, as he has put together back-to-back sub-2.00 ERA seasons, his first two in the big leagues, and has four more years of team control.
It would be abject lunacy for any team to trade away such a commodity, but if such a disastrous franchise exists it is the Pittsburgh Pirates.
The Buccos have a long history of jettisoning stars in their prime like Gerrit Cole, Jason Bay, Jason Schmidt and Aramis Ramírez, just to name a few. Pittsburgh general manager Ben Cherington has made clear the team has no intention of trading the generational Skenes this winter, but what if Dombrowski made him an offer he couldn’t refuse?
Trading for a talent like Skenes would require completely stripmining a thin Phillies farm system. Including all three of the untouchables, Painter, Miller and Crawford, could get Cherington to pick up the phone, but to consummate a deal Pittsburgh would need to get even more. Aroon Escobar would further balance the scales and lefty Cade Obermueller, a second-round pick this past summer, could squeak a trade across the finish line.
Such a mammoth package might succeed in landing what looks to be the greatest pitcher of a generation, but the cost would be truly crippling. The Phillies’ farm system would be completely gutted, and an aging major league squad would be left with virtually no in-house reinforcements in the near term.
A franchise-altering deal like this would be risky at best and reckless at worst, but there’s perhaps no single player that could make a bigger difference to a club than Paul Skenes. It would be the win-now move of all win-now moves, but if it leads to a championship then it just might be worth it.