3 MLB Best-of-Board Props to Back for White Sox-Guardians ALDS Game 5

Winner-take-all baseball doesn’t get much better than this. The White Sox and Guardians are knotted at 2-2 after an absolute rollercoaster of an ALDS, and it all comes down to one game tonight at Progressive Field — first pitch 8:00 PM ET on TBS. Sean Burke takes the ball for Chicago against Cleveland’s Gavin Williams, and somewhere in the middle of that pitching duel, there’s a prop board loaded with value if you know where to look.

We dug through the hitting props for Game 5 and found three spots where the market is practically begging to be bet. Two Cleveland bats with a history of making contact, and one White Sox veteran who’s quietly one of the best plus-money overs on the entire slate. Let’s get into it.

Chase DeLauter Keeps Hitting When It Matters

Chase DeLauter has been everywhere for the Guardians this series, and the hits prop market knows it — his Over 0.5 Hits is sitting around -235, which tells you exactly how much the books respect what he’s doing right now. He’s hitting from the three-hole in Cleveland’s lineup, sandwiched between José Ramírez and Jo Adell, and he’s already shown he can handle traffic: back in Game 2 he reached base multiple times against this exact Chicago pitching staff, including a pair of RBI singles that kept the Guardians’ line moving.

DeLauter’s been running right around a .287 average with an OBP north of .360 through this stretch, and he’s shown no hesitation spraying the ball to all fields. Against a White Sox staff that’s going to lean on Burke for length tonight, DeLauter projects to see his fair share of at-bats, and a guy hitting at this level only needs one clean knock to cash. At odds near -235, you’re not getting rich, but you’re backing the right player in the right spot on the night it matters most.

Steven Kwan’s Contact Skills Show Up Against Burke

If there’s one hitter in this series built to frustrate a power pitcher, it’s Steven Kwan. Cleveland’s leadoff man has a career approach built entirely around putting the bat on the ball — he doesn’t chase, he doesn’t strike out much, and he’s historically given Sean Burke problems specifically. Kwan has gone 4-for-18 against Burke in his career with two doubles mixed in, numbers that stand out given how dominant Burke has otherwise been against this Cleveland lineup in 2026.

That matters tonight because Burke was nearly untouchable against the Guardians during the regular season — a 1.04 ERA with a 2-0 record — and was even better in relief during Game 2 of this series, allowing just one hit over 5.1 innings. Kwan is one of the few hitters with a track record of getting to him. His Over 0.5 Hits sits around -230, nearly identical pricing to DeLauter, and it’s the same bet: a high-contact bat at the top of the order who doesn’t need much to get a ball through the infield. Leadoff hitters also get the benefit of extra at-bats in a game that could easily stretch deep, which only helps his floor.

Andrew Benintendi Is the Best Plus-Money Play on the Board

Here’s the one that actually jumps off the page. Andrew Benintendi’s Over 0.5 Total Bases is sitting at plus money — anywhere from +104 to +119 depending on the book — which is a rare find on a hits-or-bases prop this deep into October. All it takes is a single to cash this bet, and Benintendi gets the platoon advantage he’s needed all series: Cleveland is sending out right-hander Gavin Williams, which is exactly the matchup that’s kept Benintendi, a lefty bat, in the lineup all year.

He sat out Game 3 against a lefty-heavy Cleveland pitching plan, but with a traditional right-handed starter on the mound tonight, Benintendi projects right back into Chicago’s lineup in a middle-of-the-order spot. He’s a professional hitter with real pop in his bat — any single, double, or long ball clears this number instantly. Getting a game-changing hitter at plus-money odds on the biggest night of the series is exactly the kind of mispriced prop worth jumping on before it moves.

Lock These In

Winner-take-all games are chaos, but these three bets are about as clean as it gets on a crowded prop board. Two contact hitters at the top of a dangerous Cleveland lineup, and a White Sox veteran getting a plus-money number he shouldn’t be getting. If you’re looking to add a little juice to Game 5 without overcomplicating things, this is the move — check your player prop search tool to confirm the latest lines before first pitch.

• Chase DeLauter Over 0.5 Hits (around -235/+174)
• Steven Kwan Over 0.5 Hits (around -230/+171)
• Andrew Benintendi Over 0.5 Total Bases (around +104/+119)

Three different players, three different vibes, one common thread: all of them are in spots where the odds are working in your favor. Get these in before first pitch and enjoy the winner-take-all show.