The Philadelphia Phillies bet a lot on Andrew Painter, and so far that bet has come up short. The former wunderkind hasn’t been the same since undergoing Tommy John surgery, and the whispers that he may never be a productive major leaguer are growing louder. They’ve invested too much into Painter to trade him at the nadir of his value, but at the same time, they can’t play him and continue to throw away games. The question begs asking: what if they had drafted someone else back in 2021?
Five years isn’t a lot of time when it comes to evaluating draft classes. Most of the kids who were taken are still in their early-to-mid-twenties and have plenty of time to develop into the stars their teams envisioned on draft day. And yet, it’s a large enough sample that some conclusions can be drawn.
For instance, the Pittsburgh Pirates’ decision to cheap out with the first overall selection and draft Henry Davis is looking like a bust. The same can’t be said about Painter to this point, but he’s certainly done nothing to reassure Phillies fans that things will turn out okay.
The 23-year-old dominated minor league competition up until he went under the knife in 2023, costing him all of that season and the next. Upon his return in 2025, Painter was lit up in Triple-A. In spite of that, Phillies president of baseball operations Dave Dombrowski handed him a spot in the starting rotation on Opening Day of this year, and it didn’t go well. In 14 appearances with the Phillies, Painter was blasted for a 7.06 ERA. Things finally became so untenable that Painter was unceremoniously demoted back to Triple-A last month.
The Phillies have been slow playing his return to minor league action, and his most recent blow-up last Friday should scuttle any hopes of seeing him in the majors again anytime soon. The disappointment that was the Andrew Painter experience has opened up a gaping hole in the Phillies’ rotation, one which will need to be filled at the trade deadline. Considering the fact that Painter’s inability to pitch at the major league level will cost the team prospect capital at the trade deadline, could the Phillies have avoided this by drafting someone else in his stead?
The Phillies didn't have to draft Andrew Painter, so who else could they have taken?
Conveniently, a pair of pitchers that went after Painter have been dealing for their teams this year. The St. Louis Cardinals’ Michael McGreevy (18th overall pick) has worked to a fantastic 3.01 ERA over 18 starts this season, while Gavin Williams (23rd overall) of the Cleveland Guardians has posted a 3.81 mark in his 19 starts. Drop either of those two into the Phils’ collection of hurlers and all of a sudden they don’t need to trade for one.
Unfortunately, the Painter draft what-ifs don’t stop there. The outfield has been a persistent trouble spot for the Phillies, and they currently have only one trustworthy player on the grass in Brandon Marsh. Just two picks after the Phillies took Painter, the Milwaukee Brewers grabbed Boston College product Sal Frelick, who put up a rock solid .756 OPS in 142 games last season and took home a Gold Glove Award in 2024.
With the 27th overall selection, the San Diego Padres scooped up a Maryland high schooler named Jackson Merrill. The 23-year-old centerfielder has scuffled this year, but has an All-Star selection and Silver Slugger Award to his name, to go with a lifetime .264/.310/.446 slash line. Either one of those guys would massively improve the Phillies’ outfield woes.
What about shortstop, the position that granite glover Trea Turner somehow still occupies? Look no further than 22nd overall pick Colson Montgomery, who hit the ground running upon making his major league debut last season and has a .228/.306/.469 line across his first 162 big league games.
Catcher is a similarly disappointing spot on the diamond, as longtime best catcher in baseball J.T. Realmuto is a shell of his former self. Unfortunately, Dombrowski saw fit to sign him to a three-year, $45 million pact last winter out of desperation. Perhaps the No. 31 selection, Joe Mack, could have prevented that catastrophe, seeing as he blasted 60 homers in the minor leagues and has seven so far in 60 major league games.
Looking back, the 2021 draft may not produce any transcendent talents. Still, there were plenty of productive players who are making a difference in the major leagues five years later. Whether it’s because of injuries, mentality, or simply not being as talented as everyone thought, Andrew Painter has not been one of them.
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