The Cleveland Guardians are counting on a splashy debut from Parker Messick in a high-stakes midweek tilt with the Arizona Diamondbacks. The rookie right-hander will face Brandon Pfaadt, a right-hander who’s struggled to a 5.08 ERA in 2025, as Cleveland looks to inch closer in the wild-card chase despite sitting 9.5 games behind in the AL Central. The betting board sets Cleveland as an underdog on the moneyline but with a slim path to an upset, aided by Ramirez’s hot bat and a D-Backs lineup that’s been reconfigured at the deadline.

Jose Ramirez looms as the key fantasy centerpiece, carrying pension-level power against right-handers and a recent surge that has him flirting with a .300 clip over the past week. Pfaadt’s struggles—high contact, high hit totals, and bottom-tier expected metrics against lefties—offer a clear target for Cleveland’s offense. The series odds lean toward a tighter, possibly scrappy win for the Guardians as Messick’s debut adds an unpredictable edge to a club desperate to gain ground.

The pick for Wednesday centers on Cleveland snagging the outright upset, with Cleveland moneyline at +104 as a plausible angle if Messick delivers a clean, efficient first outing. Ramirez’s homer potential and Pfaadt’s vulnerability to the Guardians’ right-handed power could shape a favorable afternoon for fantasy managers tracking debut jitters and bullpen leverage as this series unfolds.

Three prime home-run props headline the Aug. 20 MLB slate: Jose Ramirez vs Brandon Pfaadt, Nick Kurtz vs Bailey Ober, and Kyle Schwarber vs Luis Castillo. Ramirez sits in a strong offensive window, carrying a .300+ clip recently and a track record of dingers against right-handers. Kurtz, thriving at .306 with 25 homers, draws a favorable right-hander in Ober who has coughed up plenty of deep balls. Schwarber, pacing the NL with 44 homers, faces Castillo but owns a solid .300 average and power against righty pitching. The bets carry varied upside with Ramirez at +425, Kurtz at +245, and Schwarber at +200, offering distinct paths to fantasy points or DFS value in a day with multiple afternoon starts.

The breakdown centers on matchups and recent form. Ramirez’s potential to exploit a right-hander with a late-season surge is tempered by the Diamondbacks’ bullpen, but his seven-day .300+ rate and 21 HR vs RHP tilt the odds. Kurtz’s breakout year, especially versus right-handers, is underscored by Ober’s homer-prone history (24 allowed in 20 starts, 17 since June 1). Schwarber’s career dominance of Castillo and his NL-leading HR pace add a high-upside element, even if Castillo has been stingy at times. Odds are dynamic, but each pick ties directly to recent production and favorable platoon angles, making them compelling targets for fantasy managers and prop bettors alike.

The Guardians and Diamondbacks traded blows in a tense Game 2, with Cleveland and Arizona answering every score in a see-saw duel that swung on offense and bullpen depth. José Ramírez sparked Cleveland’s early offense with a walk that helped set up Carlos Santana’s RBI single and Nolan Jones’s run-scoring hit, while Ramírez later delivered his 26th homer of the year. Brayan Rocchio showed patience at the plate, working a six-pitch walk in a critical late-inning sequence. For Arizona, Corbin Carroll’s fourth-inning triple and Lourdes Gurriel Jr.’s late-two-RBI single flipped the script and handed the Diamondbacks a precarious lead they would hold to the finish. In a game where every rally mattered, Diamondbacks relievers navigated the eighth, while Guardians late threats fizzled with runners at the corners and two outs. For fantasy managers, this one underscored how quickly momentum can shift in a volatile ballpark series and highlighted a few players whose rosters and matchups should be weighed with priority and risk in upcoming games.

Key moments included a read-and-score sequence on a Ramírez read on a quick David Fry development, a sixth-inning stand by Cleveland’s starter Tanner Bibee before Arizona rallied, and back-to-back offensive bursts that stretched into extra innings of regulation. The Guardians showed resilience but left the decisive opportunity on the table in the eighth as Arizona closed the door. The result tightens the series to a nail-biter, with both clubs carrying impactful fantasy implications at the plate and on the mound.