Pittsburgh Pirates vs Chicago Cubs Picks and Predictions May 26th 2026

Cubs turn to Jordan Wicks vs. Pirates, hope to stave off 10th straight loss

Jordan Wicks will make his season debut on Tuesday night as the Chicago Cubs try to snap a season-long nine-game losing streak when they face the host Pittsburgh Pirates.

The left-hander will hope to bolster an injury-plagued Cubs rotation when he opposes Pittsburgh right-hander Braxton Ashcraft (3-2, 2.89 ERA).

Wicks was called up from Triple-A Iowa on Sunday after Edward Cabrera was placed on the 15-day injured list with a blister on his right middle finger. Wicks, who started the season on the IL due to left elbow inflammation, has made 17 career starts since 2023 and has a 5.21 ERA. He pitched primarily as a reliever in 2025, going 0-1 with a 6.28 ERA in eight appearances (14 1/3 innings).

He is 1-0 with a 1.80 ERA in one career start against the Pirates.

However, pitching was not the issue for the Cubs in Monday’s opener after a strong six-inning, one-run start from Ben Brown.

Chicago reverted to its recent offensive futility with its only run produced by Michael Busch’s sixth home run of the year in the fifth inning of its 2-1 loss.

Excluding the five runs scored Sunday in an 8-5 setback against the Astros, the Cubs have scored a total of eight runs in six of their past seven games.

Chicago’s struggles have been mystifying as the team, which has already put together a pair of 10-game winning streaks, is a loss away from its first 10-game losing streak since June 4-16, 2022.

“It’s been a pretty challenging stretch, and it’s hard to see the bright spots right now,” Busch said. “It’s been a season of extremes. It’s kind of hard to wrap your head around it.”

The Pirates continue to score first, going 25-11 when they do and 3-15 when they don’t.

Pittsburgh has also had a power surge this season thanks to its offseason additions, and occasionally from even its struggling hitters such as catcher Henry Davis, who hit the decisive solo home run in Monday’s win. The Pirates have hit 56 home runs in the first two months of the season, which is nearly half of their major league-worst 117 they hit all of last season.

Ashcraft has also been a positive, giving Pittsburgh depth in its rotation behind ace Paul Skenes and veteran Mitch Keller.

Ashcraft matched a career high with nine strikeouts, walked two and allowed one run on four hits over seven innings in a 6-2 win last Thursday at the St. Louis Cardinals. It was the second time this season Ashcraft struck out nine in a game; the other time was against the Cubs on April 11 when he gave up one run on four hits and one walk in five innings, finishing with a no-decision in a 4-3 win for the Pirates in 11 innings. Ashcraft has compiled a 1.91 ERA with 26 strikeouts and four walks in his four starts in May.

Ashcraft has pitched at least 6 2/3 innings in each of those starts, and he has been a workhorse, pitching 62 1/3 innings this season through his first 10 starts.

“Stack quality starts, stack quality outings and I think that us as a staff, in general, have done a really good job of that in general and it’s something that we talk amongst ourselves and the importance of doing that and it’s something that we hold a lot of pride in,” Ashcraft told Sportsnet Pittsburgh last week.

–Field Level Media