Pittsburgh doubles down on Cherington through 2027 as Don Kelly stays aboard, signaling loyalty over a quick rebuild. The ownership stance hints payroll limits while promising a path to contention—yet fans should brace for the same old script: a pitching edge touted as “close” to winning, with a fragile offense and a lineup that feels cobbled together for 2026. Triolo at leadoff and Davis slumping highlight Big League questions that fantasy managers must navigate.

The piece frames a hodgepodge roster and a front office posture more focused on resources than wild spending. For fantasy souls, the key angles are Davis’s return to form, Triolo’s speed-game upside, and any midseason payroll looseness that could unlock midlevel depth. Monitoring these threads could yield discreet value amid the Pirates’ stubborn ceiling.

Oneil Cruz jumps back to the Pirates leadoff spot as Jared Triolo slides to the two-hole, reshaping Pittsburgh’s order for the Oakland series. Tommy Pham returns in left, with Reynolds, Horwitz and McCutchen anchoring the heart of the lineup, while Horwitz at first and Yorke at second bolster defensive stability. Bubba Chandler makes his third MLB start at PNC Park, aiming to rebound after a rough Brewers turn but buoyed by a five-inning perfect stint against Washington. First pitch is 6:40 p.m.

Expect Cruz to drive more runs and steals from the top, but note his stronger numbers come when leading off; the rest of the order looks to maximize on-base opportunities behind him. Chandler’s development remains a key storyline for Pirates investors as they chase wins in 2025.