Chris Welsh’s favorite long-shot dinger bet is Jackson Chourio +430 against the White Sox. He noted a 17 mph breeze blowing straight toward Chourio’s pull field in American Family Field and a Chicago pitching staff that has already surrendered 1.6 HR/9 to right-handed bats. Chourio has produced a 44 % hard-hit rate and a max-EV north of 112 mph in his first month, so Welsh expects any elevated fastball to leave in a hurry. He paired the home-run ticket with Chourio total bases in DFS slates, projecting a multi-extra-base-hit day if the wind holds.

Dylan Rockford leaned to the full-game under 8.5 in Brewers-White Sox. He pointed out that Milwaukee’s opener Patrick owns a 2.45 ERA and has yet to allow more than two runs in any start, while Chicago’s moribund offense is averaging just 3.38 runs per game at Guaranteed Rate Field. Rockford added that the White Sox posted double-digit runs only once all month and remain a bottom-three lineup against right-handed pitching. With Milwaukee scoring a full run more on the road (4.8) than at home but likely content to play from ahead behind a rested top-eight bullpen, he projects a 5-2 or 4-2 type finish and prefers the under to choosing a side.

Scott Reichel jumped on Brewers –1.5 at –110, fading White Sox lefty Garrett Burke (1-4, 6.00 ERA) and an offense sitting in the league’s bottom tier across every meaningful metric. Milwaukee’s opener, Patrick (2.45 ERA),doesn’t work deep but hands the ball to a rested, top-eight bullpen. Chicago is a league-worst 6-22 against right-handed pitching and 3-12 in Burke’s last 15 appearances dating back to 2024. With run-differential trends pointing squarely against the Sox, Reichel expects Milwaukee to win comfortably and sees the run line as the best way to trim –180 moneyline juice.

Lindquist flagged Andrew Benintendi as a sneaky long-ball target, recommending any price longer than +430 for a home-run prop. Benintendi owns a 20-plus degree average launch angle this year, and opposing starter Chad Patrick allows an almost identical 23.2-degree launch angle to hitters. That combination of loft and mediocre hard-contact suppression creates ideal conditions for a fly ball to leave the yard, especially on a mild night on the South Side.

Kenny G called the Brewers a potential “lock of the day” at –180 because of the extreme gap in starting pitching and lineup quality. He noted Chad Patrick’s 2.45 ERA and run of five straight outings with two or fewer earned runs, saying the rookie keeps Milwaukee in every game even though the club is only 2-3 in those starts thanks to a still-shaky but improving bullpen (4.74 ERA). Offensively, Milwaukee sits 5th in runs scored, 10th in OBP, and just hung 13 runs over the first two games of the series, with rookies Jackson Chourio and Joey Ortiz “raking.” By contrast, Sean Burke brings a 6.00 ERA for the 7-23 White Sox, has surrendered at least one homer in five straight appearances, and hands the ball to a bullpen trending the wrong way at 4.40 ERA. Chicago is dead last in batting average, second-to-last in slugging, third-worst in OBP, and owns only 97 total runs. The Sox are 4-9 at home while Milwaukee is merely 6-11 on the road, but Kenny believes the massive talent gap means the Brewers win “the vast, vast majority of the time,” justifying the hefty moneyline price.

It's The Final Round said Willson Contreras is in a smash spot for a base-hit prop against White Sox call-up Sean Burke. Burke leans on his slider 41% of the time and is coughing up a .290 average and 4 HR on that pitch; Contreras owns a .273 mark (3-for-11, 1 HR) versus sliders this season. The four-seam fastball (31% usage) has been even worse for Burke (.333 BA allowed) while Contreras is crushing heaters at .385 (5-for-13). Burke’s curve (.286 BA allowed) and sinker (.300 BA allowed) offer no safe haven, and Contreras is batting .500 against curves and .267 against sinkers in limited samples. With a hit in 19 of his last 20 games, Final Round expects Contreras to extend the streak and likes him for single-prop or parlay legs to record a hit (and even sprinkle on total bases).

Carty advised taking Sean Burke UNDER 4.5 strikeouts at -150. THE BAT X shows a 65% hit rate and a $13.65 expected value because Guaranteed Rate Field grades as the fourth-worst stadium for strikeouts, suppressing K upside even for power arms.

Peterson laid -1.5 runs at +100 on Milwaukee because rookie Sean Burke owns a 6.00 ERA, 6.52 FIP, 2.3 HR/9 and 3.7 BB/9 for Chicago, while Chad Patrick has sparkled with a 2.47 ERA overall and an even better 1.88 mark in his starts. Chicago’s offense averages a league-low 3.4 runs per home game, making a multi-run Brewers victory the most likely outcome. His number was Brewers -1.5 -124.

Guy Boston targeted Andrew Vaughn UNDER 1.5 hits + runs + RBIs, a prop he says he has "been gashing on" all season. Vaughn remains ice-cold at the plate and is stuck in an offense that has cleared four runs in only seven of 29 games, slashing the odds he picks up ancillary counting stats even if he squeaks out a single. The match-up is equally grim: Tobias Myers gets a weather boost with wind blowing in and light rain at American Family Field, and Milwaukee’s rested bullpen can take over early if Myers falters. With the game total sitting around 7.5, Boston sees almost no game script where Vaughn reaches two combined events and would play the prop to –120.

Guy Boston leaned to Chicago’s team total UNDER 3.5 at American Family Field. Forecast calls for wind blowing in with light rain, pushing the game total to a modest 7.5. Brewers rookie Tobias Myers gets a “bounce-back” narrative after a shaky debut, and Boston notes that despite White Sox right-hander Shane Smith’s respectable numbers, Chicago’s offense remains bottom-three in both OPS and hard-hit rate on the road. Myers’ four-seam/change combo profiles well against a Sox roster that owns a .284 wOBA versus change-ups. If conditions suppress the long ball, Boston doubts Chicago strings together enough hits to reach four runs.

Cash Out Sports Picks endorsed Milwaukee on the moneyline, stressing how badly the matchup tilts toward the Brewers. Chicago is just 7-21 overall and 4-8 in its own park, surrendering 26 runs across the last four games at Guaranteed Rate Field. Even during Milwaukee’s recent four-game skid the bats stayed lively, plating at least five runs in three of those contests. Historically the Brewers have owned this series—nine wins in the last ten meetings, six by three or more runs. The tout added that rookie right-hander Shane Smith is making his first MLB appearance against a lineup that has already posted a .737 OPS versus first-time starters this season, while only three White Sox hitters have ever faced Brewers starter Tobias Myers (and they’re 2-for-7 combined). With Milwaukee possessing the deeper bullpen and far steadier defense, the host called this the perfect “get-right” spot for a club still hovering around .500.

Dylan Rockford bet full-game under 8 (laid –120) for Brewers–White Sox after making the total 7.6. He likes what Shane Smith has shown—2.31 ERA over his last four and all four contests cashing unders—and expects another pitcher-friendly environment with 15-mph winds blowing in at Guaranteed Rate Field. Opposite Smith, Tobias Myers surrendered only two runs across four innings in his MLB debut; Rockford anticipates Milwaukee will lengthen him out to 70–75 pitches but concedes walks (four in that first start) are the lone concern. Given two middling offenses and unfavorable hitting weather, he projects a 4-3 type game and will play any number 8 or higher.

Malcolm Bamford targeted a Brewers first-five team total under (2.5 or better) because he trusts Shane Smith to keep Milwaukee silent for the first trip through the order. Smith just struck out seven Twins in a 1-0 loss and owns a 0.96 WHIP at home. Bamford warned that the White Sox bullpen and offense make full-game wagers dicey—Chicago has lost games Smith has allowed only one or two runs—but isolating the first five removes that variable. With Tobias Myers still on a pitch count and Milwaukee batting only .231 versus righties, Bamford projects one, maybe two early runs at most for the Brewers.

Brian Howard is firing on the White Sox first-five moneyline at roughly +145 because he trusts Shane Smith far more than Tobias Myers. Smith carries a sparkling 2.30 ERA and sub-1.00 WHIP, while Myers owns a 4.50 ERA and an ugly 2.00 WHIP. Howard cashed this exact pitching mismatch the last time it aired and sees no reason to deviate from the "good arm vs traffic machine" formula. Isolating the first five removes Chicago’s shaky bullpen from the equation, and Howard will also look at Smith’s strikeout over (projected 4.5) since the Brewers whiff nearly 25 % of the time against righties.

Ron Romanelli advised playing the full-game under in Brewers vs White Sox. He pointed to Chicago rookie Shane Smith’s eye-opening 2.30 ERA across 27.1 innings with only one homer surrendered, calling him the best arm in a bad rotation. The problem, Romanelli said, is the White Sox still field MLB’s lowest-scoring offense, so even Smith’s quality starts rarely push totals over. Tobias Myers gets what Romanelli called a bounce-back opportunity after a shaky outing; the right-hander faces "the weakest lineup in baseball" and owns a strike-throwing profile Romanelli trusts to keep traffic minimal. Given two competent starters, an anemic Chicago lineup, and Milwaukee’s own inconsistent bats, Romanelli projected a slow, low-run affair and told listeners to bet the under.

Lindquist circled Christian Yelich’s 1.5 total-bases prop as one of his favorite plays on the card. Chicago is expected to use an opener before turning the game over to swingman Shane Smith and a White Sox bullpen Lindquist labeled “confirmed, not good.” Even though Smith has given up only one homer so far, his 45% hard-hit rate and lack of swing-and-miss stuff set up well for gap-power lefties like Yelich. The former MVP already owns a .385 xwOBA against right-handed pitching this season and has elevated his fly-ball rate by nearly six percentage points. With the wind blowing out to right at Guaranteed Rate Field and Milwaukee projected for 4.9 runs by most models, Lindquist expects Yelich to collect at least two bags—whether via a double, a pair of singles, or clearing the fence.

Peterson played Brewers -1.5 at +100, grading the true price -137. Tobias Myers has been a revelation since debuting in 2024 (3.04 ERA, 8.2 K/9, 2.5 BB/9) and faces a White Sox lineup scoring only 3.5 runs per game at home, second-worst in MLB. Chicago’s Shane Smith owns a sparkling 2.30 ERA, but his 3.32 FIP, 7.2 K/9 and 3.0 BB/9 scream regression—especially with minimal run support. Peterson expects Milwaukee’s offense (4.9 runs/game) and bullpen depth to turn a win into a multi-run cushion.