home MLB Free Picks Red Sox vs. Pirates Expert Free Pick August 16, 2026

Red Sox vs. Pirates Expert Free Pick August 16, 2026

Boston Red Sox vs Pittsburgh Pirates MLB Free Pick

The Angle(s): This looks like a prime spot to fade the Pittsburgh Pirates, who were shut out Saturday and continue to struggle immensely against left-handed pitching, sitting at just 11-24 (-43% ROI) versus southpaw starters this season. Boston turns to left-hander Patrick Sandoval (1-1, 3.30 ERA), and the Red Sox have won four of his five starts since he entered the rotation. Sandoval held Pittsburgh scoreless over seven dominant frames in his lone previous career start against them.

The Pirates are closing out the week relying heavily on a taxed bullpen game. Their middle relief corps has shown noticeable strain recently, giving Boston’s lineup plenty of late-game advantages to exploit.

The Bet: Red Sox -114 (3%). 

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Mike Lundin

A former poker pro, Mike Lundin made his picks available to the public in June of 2014. The late start didn't stop him from finishing as the #8 handicapper overall for the year with a profit of $34,970 for $1,000/game clients! He has since racked up multiple Top 10 finishes across several sports.

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