Kenny G tagged the White Sox at +160 as a live underdog because Chicago’s South-Side crew quietly has the better recent form on both the mound and at the plate. Cubs starter Ben Brown sits at 4-7 with a 6.48 ERA and has been "obliterated" in three of his last four outings (vs Phillies, Cardinals, Royals). The Cubs’ bullpen is a middling 3.80 ERA, and their offense has cooled—recent runs: 6, 6, 4, 6, 4, 1, 6, 4. Meanwhile, 25-year-old Sean Burke has delivered four quality appearances in his last five (4.19 ERA) and draws a second crack at the Cubs after mid-May struggles. The White Sox bullpen is a respectable 4.00 ERA, and their hitters have erupted for 12, 11, 8, 7, 10 and 10 runs in six of the last eight contests. With the market hanging Cubs –193, Kenny thinks the price overrates Chicago’s brand name and underrates recent performance, calling the Sox a potential "dog of the day."

While acknowledging the Cubs should win, Mark said the smartest way to attack the Crosstown Classic is White Sox +1.5 at +105. Chicago’s South-Siders own MLB’s best OPS over the past two weeks and have cashed the run line in nine of their last ten games. With the Wrigley wind forecast uncertain and the total already at 9.5, he expects both offenses to score, making the extra run of insurance plus money ‘too juicy to pass up.’

Brad Pick Dawgz played the Cubs team total over 4.5 runs, arguing that Friday’s blowout loss leaves Chicago’s lineup "pissed off" and primed to respond. He specifically wants to fade Aaron Savale after the right-hander’s best outing of the year, expecting immediate regression. With the White Sox riding an unsustainable hot streak and Savale due to come "back down to earth," Brad projects the Cubs’ offense to plate at least five runs.

Lonte Smith singled out Dansby Swanson as his favorite home-run prop for Friday. Smith noted that Swanson has a four-game hitting streak and believes Chicago’s lineup is poised for another multi-run eruption against White Sox rookie Colin Hauser. Earlier in the show he flagged Hauser’s contact luck—17 hits but only four earned over his last two starts—and pointed to the Cubs’ NL-leading hard-hit rate since the All-Star break as evidence that regression is coming. With the wind blowing across Guaranteed Rate Field rather than in, Smith expects several elevated balls to carry and likes Swanson’s odds of leaving the yard, describing the market price (typically +425 to +450) as “a touch short for how well he’s barreling right now.”

Lonte Smith countered by laying –1.5 runs with the Cubs, citing an eight-game winning streak in the Crosstown Classic where Chicago has outscored the White Sox 26-8 this season alone. He sees regression coming for Colin Hauser, who has allowed 17 hits but only four earned in his last two starts, and expects the contact luck to dry up against a Cubs lineup that paces the NL in hard-hit rate since the All-Star break. With Shota Imanaga back in mid-season form (0.90 WHIP since returning) Smith projected a 4-2 type victory and likes tying Cubs –1.5 into run-line parlays with Milwaukee or Texas.

Scott Reichel grabbed the White Sox around +160, arguing the market has over-corrected toward the Cubs. He highlighted starter Colin Hauser’s absurd home splits—4-0 with a 0.69 ERA at Guaranteed Rate Field—and the fact Chicago has won five straight Hauser starts while averaging more than five runs per game during that stretch. The South Siders just swept Pittsburgh and took a series from Tampa, so their current form is far better than their season record. Reichel does respect Shota Imanaga’s post-injury dominance (three earned total over his last three outings) but still leans under 8.5 given cross-winds and both pitchers’ strike-throwing profiles. He sees the plus-money side as mispriced in what he expects to be a tight, low-scoring contest.

Lindquist’s favorite plus-money play is the White Sox money line around +165 against Shota Imanaga. The Cubs left-hander owns unsustainably lucky indicators—a sub-.200 BABIP and 90 % strand rate—despite a fly-ball profile in warm South-Side conditions. Lindquist anticipates sharp negative regression once balls start falling in, noting Imanaga’s 45 % hard-hit rate. Although Chicago’s offense is poor overall, the price more than compensates given the matchup. He acknowledges Adrian Houser isn’t a shutdown arm but points out Houser’s barrel rate has improved and that the market is over-reacting to Imanaga’s gaudy 1.89 ERA. He believes fair odds should be closer to +140.

Lindquist labeled the White Sox his favorite value play, taking their money-line around +165 versus Shota Imanaga and the Cubs. The left-hander’s surface ERA (1.89) is propped up by an unsustainably low .199 BABIP and a strand rate near 90%, metrics destined for regression given his extreme fly-ball profile. South Side winds and decent hitting weather only enhance that downside. Meanwhile Adrian Houser’s barrel rate has plunged and pitch-model fastball run value has spiked, giving the Sox a fighting chance on the mound. Lindquist sets Chicago closer to +140 and is content eating the variance on a bad team when he’s picking up 25 cents of expected value.

The under is the second play, driven by a projected pitchers’ duel. Hauser has only allowed 16 runs in 62 innings despite soft contact tendencies, while Shota Imanaga has given up just 21 runs over 75 frames and regularly strings together shutout stretches with high strikeout totals. The White Sox average a meager 3.7 runs per game and face a Cubs staff positioned to blank them. Given both starters’ recent form and Chicago’s punchless offense, Cash Out Sports Picks expects a quiet scoreboard.

Drew Martin recommended taking the White Sox at +165 in the Crosstown Series opener thanks to Adrian Houser’s breakout and several situational edges. Houser is 5-2 with a 1.89 ERA, allowing one earned run or fewer in three of his last four appearances—all while touching 96 mph more frequently as the season progresses. Chicago’s South Side offense is the second-hottest in MLB by wRC+ over the past week and profiles better versus lefties like Cubs starter Shota Imanaga (7-3, 2.50 ERA but just 2-2 in his last four decisions). Martin also highlighted a potential look-ahead for the Cubs, who trail Milwaukee by one game and face the Brewers next. With the White Sox bullpen showing recent improvement, he believes the fat plus money is worth the swing.