Pirates at Cubs: Betting pick leans to Pittsburgh as Ashcraft faces Taillon

The recommended best bet for Monday’s Major League Baseball matchup in Pittsburgh is the Pittsburgh Pirates at +102 on FanDuel, with a suggested $50 wager, according to a New York Post betting preview.

Pittsburgh will send right-hander Braxton Ashcraft to the mound, while the Chicago Cubs plan to start Jameson Taillon. Ashcraft has allowed three runs over his last 21 2/3 innings, a stretch that has underpinned the betting pick. Taillon, meanwhile, is 5-4 on the road this season and has been characterized in the preview as a middling option away from Wrigley Field.

The play listed in the preview is intended as a value bet: the Pirates’ moneyline of +102 implies only a slight underdog status while Ashcraft’s recent run prevention suggests he can keep the game within reach. The New York Post column singled out Ashcraft’s 21 2/3-inning streak as the key analytic point and contrasted it with Taillon’s ordinary road numbers.

Chicago’s Taillon has been a regular in the Cubs’ rotation and carries experience in high-leverage starts, but the preview frames his recent road results as less compelling than Pittsburgh’s starter. The matchup will be decided in part by each club’s ability to manufacture offense against opposing pitchers and how each bullpen performs late in the game.

Oddsmakers have set the line close to even, reflecting an expectation of a competitive game in Pittsburgh. Bettors considering the play should account for game-day conditions, lineup changes, and any late scratches, as well as their own bankroll management. The New York Post’s betting column recommended the specific $50 stake on the Pirates at +102 as the preferred single-game wager for Monday’s start.

The game will provide a test of whether Ashcraft’s recent effectiveness continues and whether Taillon can translate his road starts into a winning outing for the Cubs. Further updates on starting lineups and weather will be available closer to first pitch.