Kenny G leaned to Over 8 at Wrigley, arguing that shaky relief units and a red-hot Cubs lineup create a run-fest. Chicago’s North-Siders sit second in MLB in runs and are top-10 in average, OBP, and SLG, having posted 17-13-1-5-5-2-6 in their last seven. Jonathan Cannon (3.60 ERA) has been "serviceable" but draws a brutal assignment, while the White Sox bullpen remains a liability at 4.60 ERA. On the other side, Colin Rea (2.48 ERA) has cooled off, and the Cubs pen (4.40 ERA) invites late fireworks. Series context matters—games one and two finished 13-3 and 7-3—and Wrigley trends support offense (Cubs 13-7-2 to the over at home). Although the South-Siders’ lineup is 28th in runs, Kenny expects them to scratch a few against middling relief, making eight runs a modest hurdle. He refused to lay −300 or chase a +240 dog and instead labeled the total the best value.

Morgan compared Crow-Armstrong to a discount Kyle Tucker for DFS purposes: 12 homers, 14 steals and platoon success versus righties. At $5,000 he draws Jonathan Cannon, whose 3.60 ERA masks a .271 average allowed to left-handed bats. Morgan projects multiple chances for PCA to swipe a bag or take Cannon deep in a crosstown Wrigley wind game.

Although Morgan believes Rea’s 2.48 ERA won’t stick, he still recommends the $7,200 right-hander because even a 4.29 ERA version suffices against the White Sox, who sit last in OPS and just 28th in runs. Rea’s cutter/curve mix held opponents to a .214 average so far, and with the South Siders striking out 24.9% of the time, Morgan expects Rea to pay off as a salary saver that lets gamers jam in premium bats.

In his Cubs/White Sox stack, Morgan highlighted Kyle Tucker ($4.3k) as the centerpiece. Tucker has already logged 10 homers and 12 steals while slugging .536 versus right-handed pitching since 2023. He’ll take aim at Jonathan Cannon, who sports a 4.30 FIP and a 5.00 career road ERA.

Morgan built a Wrigley Field mini-stack around Kyle Tucker versus White Sox righty Jonathan Cannon. Tucker sits on 10 homers and 12 steals, owning a .536 slugging percentage against right-handed pitching since 2023. Cannon enters with a 3.60 ERA but a worrisome 4.30 FIP and a 5.00 career road ERA, numbers Morgan believes will regress in the hitter-friendly afternoon conditions at Wrigley. Tucker’s $4,300 salary is justified by his across-the-board ceiling in this spot.

Peterson grabbed the White Sox at +260, noting that Cubs starter Colin Rea’s surface-level 2.48 ERA is backed by a more modest 3.22 FIP and only 7.2 K/9, hinting at regression. Meanwhile, rookie Jonathan Cannon has lifted Chicago to three wins in his last four outings with a 3.60 ERA and just four runs allowed over his past three starts. Peterson priced the Sox at +234, so the market is giving an extra 26 cents on what he views as a winnable crosstown spot.

The Bettor Mark locked in the Chicago Cubs team-total over 5.5 runs at ‑137 as one of his five best bets. He pointed to 20-mph winds howling out to center at Wrigley, a situation that historically turns routine fly balls into souvenirs. Chicago torched the White Sox for 13 runs Friday and even hung a six-spot in a single frame, showing their offense is alive and well. Saturday’s pitching matchup of Burke vs. Matthew Boyd offers little resistance, and Boyd has already given up five homers in his last three turns. Using Outlier’s prop screener he noted the better juice at 5.5 (-137) compared to 6.5 (+120), giving bettors an extra run of cushion. Despite a 30 % cash rate on this number in their last 10, Mark blamed Miami’s pitcher-friendly park for those misses and expects launch-angle fireworks in today’s ideal Wrigley environment.

Bill Harrelson advised taking Seiya Suzuki for less than 1.5 total bases on Saturday’s Crosstown Classic. Harrelson pointed out that Suzuki is slashing just .214 against right-handed pitching compared to .239 overall and draws another righty here. The Cubs outfielder has failed to reach two total bases in four of his last five meetings with the White Sox and has been held under this number in 54 % of his 2025 plate appearances regardless of handedness. Books across the market are heavily shaded to the under, which Harrelson considers confirmation that the line is a touch high.

Lonte Smith grabbed the White Sox First-5 moneyline at plus odds, backing Shane Smith’s recent form (2.10 ERA last five, two earned or fewer in four straight starts, six shutout frames in his latest outing). He pointed out that the Cubs are hitting below .200 over their last 10 games and their bullpen has imploded with a 5+ ERA, so taking Chicago full-game felt risky. By isolating the first five innings, Lonte expects Smith to outduel Jake Horton before Chicago’s league-worst relief corps can blow things up.

Scott Reichel laid the ‑1.5 run line with the Cubs, stressing that Chicago’s lineup should mash in a classic Wrigley wind-blowing-out environment while the White Sox simply cannot keep up. He noted that rookie left-hander Shane Smith owns a solid 2.10 ERA, but the South Siders remain a bottom-five offense and were shut down by Nick Martinez earlier in the week. On the other side, Chicago will face Jake Horton, who carries a 6.75 ERA and lasted only four innings against the Mets in his lone MLB appearance. Reichel projected the winning team would need at least seven runs in the expected shoot-out conditions and argued the White Sox are incapable of reaching that number, making the Cubs an auto-play on the run line at roughly even money.

Cash Out Sports Picks recommended the full-game over, noting the total has cashed in six straight Cubs games against AL opponents and sits 12-6 after their losses. Wrigley has played like a hitter’s park (Cubs average 5.6 R/G at home, 2nd in MLB). Smith’s middling profile—bottom-half K and BB rates, 8th-percentile chase rate, 39.5% hard-hit—meets a White Sox bullpen ranked 21st in ERA with 23 homers allowed. The Cubs pen isn’t much better (22nd, 4.59 ERA) and rookie Borden is still stretching out. Three of the last four head-to-heads went over, and short-rest angles on both clubs lean the same way. The tout expects plenty of crooked numbers from both sides.

Cash Out Sports Picks advised backing the Cubs on the money-line and run-line at Wrigley. He pointed out the massive gap in clutch hitting: Chicago owns a .869 OPS with runners in scoring position (2nd in MLB) while the White Sox sit 27th at .628. The Cubs also hold a .283 team BABIP versus the Sox’ .267, have taken the past five meetings, and enter rested after a Thursday off. Meanwhile Chicago’s south-siders are 16 games below .500 and have burned bettors for more than $2,400 on $100 wagers this year. Rookie starter Gordon surrendered four hits and three runs in his lone MLB appearance, and the Sox bullpen ranks 21st in ERA. With the Cubs’ deeper lineup and far cleaner recent form, the tout sees clear value laying the runs.

Kenny G said the White Sox money-line at +195 is mis-priced and worthy of dog-of-the-day consideration. His confidence comes from Shane Smith’s current form (1-2, 2.08 ERA, four straight quality starts against Miami, Kansas City, Milwaukee and Minnesota) contrasted with Chicago Cubs rookie Cade Horton making his first MLB start after a shaky four-inning relief outing versus the Mets (4 H, 3 ER). Kenny pointed out the Cubs’ 4.59 bullpen ERA and their 12-7-1 home record to the over, noting Horton will not work deep and that bullpen exposure is a liability at a –235 price. He acknowledged the White Sox offense is bottom-three in every major category but credited their bullpen improvement (4.35 ERA) and framed the crosstown rivalry as a motivation booster. Road splits (White Sox 15-8 to the under, Cubs 12-8 at home) further convinced him the market is overvaluing the Cubs, giving the Sox a real chance to steal the game at almost 2-1 odds.

Lindquist fired on Pete Crow-Armstrong to homer at +300 or longer in the Crosstown matchup with the White Sox. The rookie already owns double-digit bombs thanks to a 23-degree launch angle and 45 % hard-hit rate, and Friday’s Wrigley forecast shows 12-mph winds blowing out to right. Opposing right-hander Shane Smith allows a 41 % fly-ball rate and has just a 19 % whiff rate on his four-seam fastball. Hitting atop the Cubs order guarantees Crow-Armstrong a max plate-appearance ceiling, a key component in Lindquist’s home-run model. He assigns a true probability near 24 %, making anything north of +275 a green-light wager.

Data Skrive’s projection model spit out a 6-3 final in favor of the Cubs, giving Chicago roughly a 70% win probability that still beats the implied 69% odds of the current –225 moneyline. The model leans on three edges: a massive gap in overall team quality (Cubs 25-19 record, +46 run differential; White Sox 14-30, –72), Cade Horton’s strikeout-heavy profile that plays up in Wrigley’s cool May conditions, and a Cubs offense averaging 5.1 runs per game at home. Shane Smith’s shiny 2.08 ERA is countered by a 4.32 xERA and a White Sox bullpen that owns the worst WPA in baseball. Bettors looking to anchor parlays or same-game moneyline/under combos can comfortably ride the North Siders at this number.

Greg Peterson said the market is over-reacting to Friday’s forecasted Wrigley wind and grabbed Under 11.5 runs. He reminded listeners the White Sox are scoring fewer than 3 runs per road game (28th in MLB) and probably will not take advantage of the jet stream. Shane Smith owns a 2.08 ERA with only 1 homer allowed in 43.1 innings, so he profiles well even with the wind blowing out. On the other side, highly-touted rookie Cade Horton is stretched out after four spotless bullpen innings earlier in the month and makes his first career start. Peterson made the total 10.2, giving him more than a full run of cushion on the under.