The Phillies have spent too many October nights on the outside looking in, and this winter is shaping up as a chance to do something enormous about it. If Philadelphia wants to swing big heading into the 2027 regular season, the name at the top of the board is Tarik Skubal.
Skubal checks every box you want in a frontline starter. He misses bats in bunches, he can take over a game when he’s right, and there are stretches when he looks like the best pitcher in baseball. He also brings the kind of edge and intensity that could fit right into a Phillies clubhouse trying to change its postseason story.
The Dodgers made the biggest splash of the trade deadline by landing the two-time Cy Young Award winner, but now he’s headed for free agency. Skubal closed the 2026 season with a 12-7 record, a 2.72 ERA, and 186 strikeouts across 158 2/3 innings. After the trade deadline, his 2.2 fWAR led the majors, edging Jesús Luzardo, who finished the year with a 1.06 ERA after August 3.
Philadelphia has already shown it’s willing to aim high. The largest contract ever given to a pitcher belongs to Yoshinobu Yamamoto, who signed a 12-year, $325 million deal with the Dodgers after the Phillies reportedly put a bigger offer on the table. That kind of aggressiveness is exactly what this market calls for again, only this time the target is Skubal.
If the Phillies were to land him, the rotation would be frightening. Put Skubal in front of Zack Wheeler, Luzardo, Cris Sanchez, Andrew Painter, and Aaron Nola, and the question becomes simple: how dominant can one staff be?
The money is massive, but the fit is there. Per Spotrac, Skubal’s market value is around $40 million per year, and even with his age-30 season coming next year, a 10-year contract is still in play. Per FanGraphs, the Phillies have about $47 million coming off the books after this season, which at least makes the numbers workable.
The offense remains a concern, but the old postseason truth still hangs over all of this: great pitching travels. If Philadelphia wants the kind of edge that changes October, Skubal is the move that can do it.
Of course, a deal this big would be a huge gamble, especially for a pitcher on the wrong side of 30. It would take John Middleton and Dave Dombrowski to sign off on something in the neighborhood of $400 million or more.
But the Phillies have already put themselves in a hole. This is the kind of move that could help them climb out.
In Other News...
Phillies May Have Pulled Off Another Pitching Bargain With Jess Luzardo
Jess Luzardo arrived in Philadelphia in a trade that cost the Phillies Emaarion Boyd and Starlyn Caba, and the early return has only strengthened the idea that the club may have found another pitching bargain. After landing him, the Phillies moved quickly to lock him in, agreeing to a five-year, $135 million deal that begins in 2027 and includes a sixth-year team option.
Luzardo backed up the investment with a strong 2026 season, posting a 2.86 ERA across 179.2 innings and giving the rotation the kind of stability Philadelphia covets. Inside the organization, the belief is that the coaching staff played a major role in helping him tap into that level, which is exactly why this move already feels like more than just a trade acquisition. [Read more 🡒]
Phillies Face A Costly Jhoan Duran Decision Sooner Than Expected
Jhoan Duran has given the Phillies something they value as much as anything in October stakes: a closer they can trust late and a pitcher who could become expensive quickly. With just one year of team control left before free agency after the 2027 season, the front office is already staring at a decision that rarely gets easier with time. His performance puts him in the same conversation as the sports highest-paid relievers, the kind of company that includes recent contracts for Edwin Daz and Josh Hader.
For Philadelphia, the question is not whether Duran fits, but how high the price might climb if they want to keep him from ever getting to the open market. An extension has not been announced, and the timing matters because upcoming collective bargaining agreement negotiations could reshape future contract structures. The Phillies may decide sooner rather than later whether they want to chase a record-setting deal for a closer, or risk letting one of their most important arms become a much bigger issue down the road. [Read more 🡒]
Phillies Face A New J.T. Realmuto Question They Cant Ignore
J.T. Realmuto has been the steadying force behind the plate for the Phillies for years, and the workload has been as relentless as his reputation suggests. Since 2022, no catcher in Major League Baseball has started more games at the position, and even in a season where he still handled 122 starts, he remained one of the clubs most dependable defenders while the offense slipped a bit from his usual standard.
So when president of baseball operations Dave Dombrowski said Realmuto will catch less often in 2027, it was more than a casual planning note. The Phillies have already committed to him on a three-year deal, but they also know age and wear have to be managed somewhere, and first base could become part of the answer as they try to keep his bat and glove useful deeper into the contract. [Read more 🡒]