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Trade Idea Swaps Phillies' Andrew Painter for $3.5 Million Outfielder

Originally posted on Athlon Sports | By Jake Elman | Last updated Jun 4, 2025 10:04 AM ET

Philadelphia Phillies executive Dave Dombrowski has a history of being aggressive, and it's helped his teams win five pennants and two World Series over four decades.

The time has come for Dombrowski to make another win-now move, one involving a face he knows all too well.

During their path to the 2018 World Series title, Dombrowski and the Boston Red Sox used a seventh-round pick on Long Beach State (Calif.) outfielder Jarren Duran. Nearly a decade later, Duran is an All-Star potentially on the verge of being traded.

A reunion between Dombrowski and Duran makes sense, and it's one that Bleacher Report's Zachary D. Rymer proposed on Wednesday. Rymer suggested the Phillies go "all-in" and trade top pitching prospect Andrew Painter, along with catcher Eduardo Tait, to the Red Sox for the speedy Duran.

"Knowing how short their contention window is getting, they should arguably be looking to do exactly that sort of deal before July 31," Rymer wrote.

Duran enters Wednesday hitting .273 with 17 doubles, six triples and a .743 OPS for a fourth-place Red Sox club. He has three years of team control remaining and could either replace Johan Rojas in center field or push Max Kepler out of left field.

Duran fits the Phillies, especially in a loaded lineup already featuring Bryce Harper, Kyle Schwarber and Trea Turner. However, Rymer questioned whether trading the team's consensus No. 1 prospect and a projected future ace is worth it, even if it nets them Duran.

"They are in win-now mode, but Painter is the heir apparent for Zack Wheeler, who isn't getting any younger," Rymer said.

Andrew Painter (@Phillies) utilizes his full arsenal as he strikes out 7 in 4+ innings for the Triple-A @IronPigs. pic.twitter.com/LiCRe9GET4
— MLB Pipeline (@MLBPipeline) May 22, 2025

Painter is 2-0 with a 2.65 ERA and 20-7 K-BB ratio in 17 Triple-A innings. Tait, who turns 19 in August, owns a .285 average, eight homers, 35 RBIs and a .837 OPS at Single-A Clearwater.

Rymer acknowledged it's "doubtful" the Red Sox would decline that trade offer. He also looked at the flip side, questioning why the Phillies would do it.

"To trade a guy like that just to improve an already dangerous offense would be borderline wasteful," Rymer wrote of Painter.

This article first appeared on Athlon Sports and was syndicated with permission.

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