Deadspin | Jameson Taillon faces old club as Cubs close in on playoff spot

Sep 10, 2025; Cumberland, Georgia, USA; Chicago Cubs starting pitcher Jameson Taillon (50) pitches against the Atlanta Braves during the second inning at Truist Park. Mandatory Credit: Dale Zanine-Imagn Images

Nine years ago, Jameson Taillon was a pitching prospect with Pittsburgh, part of a core that the Pirates hoped would turn around the long-suffering franchise.

Fast forward to Monday and Taillon will take the mound, looking to help another one of baseball’s most famously tortured franchises get back to the playoffs — and the right-hander will do so against the team that first turned to him nearly a decade ago.

Taillon, 33, will be on the mound for Chicago on Monday when the Cubs visit Pittsburgh for the first of a three-game series — the opening series of the Cubs’ final road trip of the season.

The Cubs (85-64) will take the field 5 1/2 games behind the National League Central-leading Milwaukee Brewers, but also sitting in the first wild-card spot in the NL, 10 games ahead of the San Francisco Giants — the first team out of a wild-card berth. Chicago is looking to get back to the postseason for the first time since 2020, when the Cubs were swept by the Miami Marlins in the wild-card round in the COVID-shortened season.

That ended a run for the Cubs of five postseasons over a six-season span — a run that included winning the World Series in 2016 to break a 108-year title drought.

Taillon (9-6, 4.15 ERA), a nine-year veteran who has played for the Pirates, Yankees and Cubs in his career, will be making his second start since being activated from the injured list after dealing with a groin strain. In his first game back on Wednesday, Taillon gave up two runs on six hits and two walks with two strikeouts over 4 1/3 innings. He did not get a decision as the Cubs won 3-2 in Atlanta.

“(Taillon) gave what we needed,” Cuba manager Craig Counsell said after the game. “You’re facing (Braves left-hander) Chris Sale and you know it’s not going to be easy to score. He wasn’t making it look like it was going to be very easy to score, that’s for sure. We did a nice job and (Taillon) hung in there and gave us a good effort.”

Taillon is 3-2 with a 4.25 ERA in 36 innings over six career starts against the Pirates, who took him No. 2 overall out of The Woodlands High School in Texas in 2010.

Opposing him will be rookie righty Braxton Ashcraft (4-2, 2.47). Postseason dreams have long been extinguished for the Pirates (65-85), who own the worst record of any team not yet officially eliminated from the playoffs. But that won’t render the rest of this season meaningless.

Much like Taillon nine years ago, Ashcraft represents what the Pirates hope will be the foundation of that long-awaited emergence. With reigning NL Rookie of the Year and current Cy Young Award favorite Paul Skenes set to take the mound Tuesday, Ashcraft will face the Cubs for the third time in his debut season.

In his first game at Wrigley Field on June 14, Ashcraft pitched the final two innings of a 2-1 Pirates loss, retiring all six batters he faced, including striking out the final two.

Then in Chicago on Aug. 15, Ashcraft got the start and was again stellar, giving up one run on three hits over five innings. He struck out four and did not walk a batter en route to a no-decision in a 3-2 Pirates win.

In his most recent outing, Ashcraft pitched three innings of relief in a game the Pirates lost 3-2 in 11 innings in Baltimore on Tuesday. He gave up one run on two hits with two walks and four strikeouts.

After the game, Ashcraft was asked what he hopes his recent performances have shown the Pirates.

“(That) I want the ball,” said Ashcraft, a second-round pick in the 2018 draft out of Robinson (Texas) High School. “I think at the end of the day, the willingness to fill roles boils down to wanting to take the ball and be on the bump. That’s how I grew up and that’s how I know this game. Go compete when you have the opportunity to. I’m looking to do more of that this year.”

–Field Level Media