MLB Free Pick: Pittsburgh Pirates at San Diego Padres — Monday, August 24, 2026

9:40 PM ET

Spread: PIT -1.5 (+165) / SD +1.5 (-200)

ML: PIT +101 / SD -111

Over/Under: 7.5

Free Pick: Pirates +101

This one comes down to the pitching matchup, not the team records. Braxton Ashcraft has been one of the better arms in baseball over the last month, allowing just two runs over his last 17 innings and carrying a 2.00 ERA in August starts. He ranks in the 77th percentile in expected ERA this season, and Pittsburgh is 17-8 in his starts, a mark that stands out on a team that's otherwise well under .500.

Robbie Ray's 3.20 ERA looks sharp on the surface, but the underlying numbers tell a different story. His FIP sits at 4.59, nearly a run and a half higher than his actual ERA, and he ranks in just the 28th percentile in expected ERA. That gap between results and process is exactly the kind of thing that tends to correct itself, and tonight is as good a spot as any for it to start.

None of this ignores the obvious: San Diego is the better team right now, riding a three-game winning streak and seven wins in its last 10 while climbing into a wild card spot. Pittsburgh's offense has cooled significantly too, ranking 20th in runs scored and 28th in OPS over the last month. But this pick isn't a bet on the Pirates' lineup. It's a bet on Ashcraft outpitching Ray, and at plus money, that's a price worth taking.

Bottom Line: Ashcraft has been outperforming his peripherals, and Ray's ERA is propped up by numbers that don't match his process. Lean Pirates +101.

Odds referenced at time of writing and subject to change. Please gamble responsibly — if you or someone you know has a gambling problem, call 1-800-GAMBLER.