The most painful trade the Phillies could make before spring training

This improbable, yet earth-shattering move would cost them dearly.
Detroit Tigers v. Philadelphia Phillies
Detroit Tigers v. Philadelphia Phillies | Michael Mooney/GettyImages

Between now and spring training, the Philadelphia Phillies have the rare opportunity to make a massive move, one that could instantly propel them into World Series favorites. However, it could become a costly one and an especially painful one for a long, long time if it doesn’t work out in the end.

That potentially painful move that could still ultimately pay huge dividends is trading for Cy Young winner Tarik Skubal of the Detroit Tigers. That’s right, one of the game’s top pitchers, if not the top already, can likely be had by the Phillies if they are willing to give up a king’s ransom of a package in return.

Selling the farm in a Tarik Skubal trade would hurt the Phillies in the long run

Skubal has won back-to-back Cy Young Awards and has ranked among the top pitchers in all of baseball across most of the major statistical categories in recent years. Last season, the 29-year-old left-hander posted a 13-6 record with a stellar 2.21 ERA, a league-leading 0.89 WHIP, along with a whopping 241 strikeouts in 195 1/3 innings.

With Skubal, you are almost guaranteed a quality start each time he takes the mound. He's one of the indisputable No. 1 aces in the league. As Zack Wheeler aims to work back into game action following his surgery, Skubal would be the perfect candidate to anchor the Phillies’ rotation to maintain their position as having one of the top starting rotations in the majors.

However, to get Skubal, Philadelphia would need to be prepared to give up at least their top position prospect and top pitching prospect, which means Aidan Miller and, gulp, Andrew Painter.

Yes, the same Painter that everyone has been anticipating for so long. He could turn out to be the next homegrown ace of the franchise. That's how the Phillies are treating him. But he would have to go without even having thrown a pitch for the Phillies at the MLB level.

And that would just be the start, as any package would need to include additional pieces. That could include some combination of Gage Wood, Aroon Escobar, Dante Nori, Jean Cabrera, and Moisés Chace among other prospects. Justin Crawford would likely be spared, given that he is in the Phillies’ outfield plans for 2026, but you never know. 

So that sounds like emptying the farm system right? That’s exactly what will be needed for the Tigers to let go of one of the best pitchers of this generation. On top of that, with just one year left in Skubal’s contract, he will hit free agency after the 2026 season, giving the Phillies one crack at winning the World Series in the potential all-or-nothing year.

If the Phillies were to win it all in 2026 with Skubal, regardless of whether he would re-sign, it could still be worth it. However, if they were to make the trade and fail to accomplish the task, with the two-time Cy Young winner leaving town right after, it could become the most painful trade that the Phillies could make in franchise history.

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