Kenny G said the betting value sits squarely on Cleveland at -140 because of a massive pitching and offensive gap. Rookie left-hander Joey Cantillo owns a 3.18 ERA in four big-league starts and has struck out 29% of batters faced thanks to a plus change-up that neutralises right-handed hitters – a key weapon against a Chicago order that carries a .616 OPS versus southpaws. On the other side Aaron Civale, who came over from Milwaukee at the deadline, has been a disaster: 11 earned runs over his last 8.1 innings and a 4.94 xERA on the season. Kenny noted that Chicago’s lineup is "flat-out unplayable," ranking 28th in runs, 30th in batting average and 29th in slugging. Even the Pale Hose’s mildly improved bullpen (4.02 ERA) can’t cover for that lack of punch. Cleveland’s pen sits seventh in MLB at 3.38, giving them a late-inning edge as well. Road splits back the move – the Guardians are 27-20-4 to the under on the road, reflecting strong run prevention – but Kenny prefers the moneyline, calling -140 fair for the vastly better team and starter.

Bill Harrelson advised taking Chase Meidroth for LESS than 1.5 hits + runs + RBIs. He noted Meidroth has stayed below this line in five straight games, 8 of his last 10 and 14 of his last 20 despite averaging 4.4 plate appearances. Versus the Guardians he has produced exactly one combined H-R-RBI in three consecutive meetings. Even on the full 2025 season the under is cashing 54 % of the time, but the real sell signal is his post-June 10 swoon: the rookie is averaging just 0.4 H-R-RBI in his most recent five home games. Every major book, including Hard Rock, has the under juiced, so Harrelson is comfortable fading the slumping bat once again.

Kenny G leaned toward Cleveland ‑150 on the South Side, believing Tanner Bybee is primed for a rebound. Bybee’s 4.35 ERA is bloated by recent rough outings versus top-tier offenses; his underlying FIP sits closer to 3.90. Chicago counters with Sean Burke, who just coughed up six earned to Toronto and was tagged for three runs in three innings by Cleveland earlier this season. Kenny trusts a Guardians bullpen carrying a 3.83 ERA far more than Chicago’s bats, which rank dead-last in MLB in both runs and batting average. While Cleveland’s offense is hardly explosive (26th in runs), Jose Ramirez’s recent tear (17 HR, .298 AVG) gives them the only elite stick in the game. The -150 price keeps it off his official card for now, but Kenny says the Guardians are the only viable side and could become a play if the number drops closer to -140.

Cash Out Sports Picks sided with Cleveland on the moneyline. Tanner Bibee’s 4-9 record masks strong underlying stuff; he’s been given three runs or fewer of support in eight of 18 starts. Chicago’s rebuilding lineup, filled with inexperienced bats, owns one of MLB’s worst offenses and has been particularly feeble against power right-handers. While White Sox starter Burke has pitched better at Guaranteed Rate Field, the Guardians’ bats have rebounded to average 6.3 runs over their last four games. The tout trusts Bibee’s arm and Cleveland’s superior lineup to secure the win.

Eric Lindquist advised laying the run line with Cleveland because he sees a clear edge: Gavin Williams versus an unnamed 'Smith' right-hander. Williams flashed ace-level stuff in his last start and, while the rookie’s 13% walk rate scares Lindquist a bit, the strikeout upside dwarfs the risk. On the other side, Smith’s underlying data is ugly—46.1% hard-hit rate and only a 20.8% strikeout clip—which Lindquist believes will let Cleveland’s contact-heavy lineup string rallies together. With the Guardians more dangerous versus right-handed pitching and Williams capable of six strong frames, Lindquist thinks the -1.5 is worth the juice despite Cleveland being the road team.

After Thursday’s rainout, Brad Francis went right back to Cleveland for game one of Friday’s doubleheader, saying he "really" likes the Guardians on the money line and even leans to them in game two as well.

Chris Welsh said Colson Montgomery needs to be scooped up everywhere after Chicago brought him back up. The White Sox sent the 1st-rounder to the complex earlier in the year to overhaul his swing and the changes are obvious: a 15% strike-out rate that matches a 15% walk rate, 82% zone-contact percentage, and 25% pulled fly-ball rate. Welsh called the tools "beyond belief" and believes those plate-skill gains open the door to a rest-of-season 20-homer, 20-steal pace if the Ks stay down. With the rebuilding Sox likely batting him near the top of the order, Welsh views Montgomery as a rare league-winning waiver add.

The tout took Chicago as a home underdog, citing Cleveland’s 3-10 free-fall over its last 13. While the White Sox are only 20-26 at Guaranteed Rate Field, that’s a massive upgrade on their 11-36 road mark. Current Chicago hitters have torched Logan Allen to a .326/.367/.457 slash in 46 career at-bats, and the Guardians’ bullpen is merely league-average (16th in ERA). Those matchup factors plus the price push the tout to the South Siders.

B Wade suggested fading Logan Allen under 4.5 strikeouts at plus money. Allen has cashed this over in only 6 of 16 starts, and just 2 of 8 on the road, averaging roughly three punch-outs per away game. He hasn’t topped five Ks in a road start since April 20, missing in five straight. Against the White Sox specifically, Allen has stayed under in all three career meetings (including four Ks earlier this season). With the southpaw’s dramatic home/road split and poor history versus Chicago, Wade believes the under is the smarter side.

B Wade took Jonathan Cannon over 3.5 strikeouts. Cannon has topped this number in 12 of 16 starts (67%) and is 6-for-6 at home, averaging 4.6 K per outing on the South Side compared to 2.8 on the road. Versus Cleveland specifically he logged 4 and 6 strikeouts in two career meetings, the six-punch-out effort coming earlier this season against virtually the same lineup. The reliable, tightly-clustered strikeout totals and friendly home split made Wade confident Cannon will notch at least four Ks again.

Eric Lindquist said to take Steven Kwan OVER 1.5 hits + runs + RBIs in the Guardians’ next game versus Jonathan Cannon and the White Sox. He pointed to Kwan’s steady underlying profile – a .282 expected batting average, only an 8.7 % strikeout rate, and a 7.9 % walk rate – noting that those metrics have stayed intact even through Cleveland’s recent quiet stretch. Lindquist likes stacking counting stats with Kwan because a single so often comes paired with a run scored atop the order, especially now that Angel Martinez is swinging it well behind him. Getting out of pitcher-friendly Houston and into Chicago should further help the top-of-the-order catalyst pile up production.

Francis grabbed Guardians money-line, reminding listeners that Cleveland has beaten Chicago in seven straight. He called the White Sox "one of the worst teams in the league" and praised how Cleveland "looked pretty damn good" while taking a series from Houston earlier in the week. With momentum on Cleveland’s side and the Sox reeling, Francis expects the streak to reach eight.

Bill Harrelson is also fading Jhonkensy Noel, playing less than 0.5 total bases in the same Guardians-White Sox matchup. Noel has logged the under in eight of his last ten and sixteen of his last twenty games. For the season he is 31-for-45 (69%) to the under, averaging only 2.5 plate appearances per outing. He has failed to record a base hit in six of his last seven road starts and owns a career .200 average versus Thursday’s opposing starter. Given the limited volume and persistent struggles, Harrelson said the half-base under remains one of the strongest value plays on his card.

Bill Harrelson advised playing Miguel Vargas under 1.5 hits-plus-runs-plus-RBIs against Cleveland. Vargas has stayed below this number in eight of his past ten and fourteen of his past twenty games. Over the 2025 season he has failed in 52 of 89 contests (58%). Only PrizePicks and Underdog are leaving the line up, suggesting the broader betting market already prices the under. Despite averaging 4.1 plate appearances nightly, Vargas has produced just 0.6 combined HRR across his last 14 starts and is slashing .210 versus left-handed pitching compared to .219 overall. He has stayed under in four of the last five head-to-heads with the Guardians, giving Harrelson confidence to fade him again.