Kenny G backed the Cubs at +105 behind Shota Imanaga, arguing the left-hander is “by far the better starter” compared to Yankees rookie Will Warren. Imanaga owns a 2.80 ERA and has allowed just two earned runs over six innings in each of his first two outings off the IL. Chicago’s bullpen sports a 3.56 ERA, while New York’s once-elite relief corps has ballooned to 4.07. Offensively the Cubs rank 2nd in MLB in runs, 7th in OBP and 4th in slugging, giving them plenty of paths to dent Warren once he exits. Kenny acknowledged the Yankees’ explosive lineup (1st in OBP, Aaron Judge in MVP form) but noted they can slump—only two runs yesterday—and the bullpen issues create late-game volatility. With superior starting pitching and plus money, he labeled Chicago the side to bet.

Bill Harrelson offered Ian Happ UNDER 1.5 hits + runs + RBIs as a bonus pick. Happ has fallen short in nine of his last ten and 13 of his last 20 games, including 10 of his last 11 where he averaged only 0.7 H-R-RBI. He is under in three of his last four meetings with the Yankees and, despite receiving 4.4 plate appearances per contest, simply is not producing. Season-long the prop is a near coin flip (48 %), but the recent cold streak plus market agreement—Fliff is shading the under—makes Harrelson comfortable fading the Chicago outfielder regardless of whether he faces a righty or a lefty.

Bill Harrelson called Cody Bellinger OVER 1.5 hits + runs + RBIs his favorite play of the slate. Bellinger has cleared this mark in 10 straight games (and 16 of his last 20), exploding for 12 H-R-RBI in the series opener and still cashing yesterday when the Yankees scored only two runs. During the 13-game heater he is averaging 4.2 H-R-RBI while logging 4.4 plate appearances a night. Season-long he owns a .285 average over 368 trips to the dish, but that rockets to .386 versus left-handed pitching—the split he’ll see today against southpaw Imanaga (who nonetheless allows just a .201 opponent AVG). With sportsbooks like Fliff and Hard Rock juicing the over, Harrelson is content to keep riding the scorching bat.

Cash Out Sports Picks backed the Cubs on the moneyline, citing a decisive advantage on the mound. Shota Imanaga enters with a 2.80 ERA and 0.98 WHIP overall, plus a dominant 1.34 ERA and .189 opponent average across 33.2 road innings. Yankees starter Warren owns a 4.70 ERA, 1.40 WHIP, and 10 walks in his last 14.2 frames, making him tough to trust. The handicapper noted New York’s recent slide out of first place and the Cubs’ offense—paced by Crow-Armstrong and Tucker—being able to match the Bronx bats. With Chicago holding the sharper starter and comparable lineup, the play is Cubs ML.

Eric Pathi said to take the Chicago Cubs at +120 in Sunday’s game at Yankee Stadium. His core angle is that Major League Baseball is a sport of streaks: teams tend to pile wins and losses in bunches rather than trade them back-and-forth. The Cubs just snapped the Yankees’ five-game winning streak with a 5-2 victory, so Chicago now qualifies as an underdog coming off a win—Pathi’s favorite profile. In contrast, he refuses to lay juice with favorites that have already won because he believes you surrender your mathematical edge. By grabbing the 20-cent dog price instead of laying –140 with New York, bettors are aligned with what his notebook-based system has shown to be long-term profitable.

Ryan Wormeli reported that Clarke Schmidt is seeking a second opinion but is almost certain to undergo Tommy John or an internal-brace procedure, effectively ending his 2024 season and wiping out most of 2025. Wormeli advised fantasy managers to drop Schmidt in all redraft formats and reallocate the roster spot—preferably to Luis Gil, who is already rehabbing and could slide into the newly vacated rotation slot. Even if Schmidt opts for the quicker brace option, Wormeli stressed the risk of setbacks still makes him dead weight in yearly leagues.

Mike Maher highlighted Luis Gil beginning a rehab assignment this weekend and recommended stashing him wherever possible. Maher admitted he viewed Gil’s 2023 breakout (3.63 ERA, 27% K-rate) as a bit of smoke-and-mirrors, but he still prefers Gil’s strikeout upside to several arms currently occupying both fantasy lineups and the back of the Yankees’ rotation. With Clarke Schmidt likely done for the year, New York has innings available, and Maher believes Gil could provide mid-rotation ratios plus double-digit strikeout potential every turn if his fastball-slider combo looks anything like last season.

Kenny G said he is leaning toward the Chicago Cubs at +140 on the moneyline and may even label them his "dog of the day." He expects left-hander Matthew Boyd to extend his strong run (9-3, 2.52 ERA; five scoreless innings vs St. Louis in his last start) against a Yankees lineup that, while hot, now faces a pitcher they have not yet seen. Kenny also pointed out that New York starter Max Fried has looked hittable in consecutive outings (seven earned runs in 11 innings versus Toronto and the Mets) and that the Yankees’ bullpen ERA has ballooned to 4.12. With Chicago ranking second in MLB in runs scored and slugging, he believes the Cubs have enough offense to punish the bullpen once Fried exits. Factoring in a bounce-back spot after an 11-0 loss, a healthier relief corps, and the attractive plus money price, Kenny advised betting Chicago +140.

Cash Out Sports Picks sided with the Yankees on the moneyline. He pointed to New York’s explosive recent offense – 8.0 runs per game over the last six – compared to the Cubs’ 4.7. Max Fried brings an 11-2 record and 2.27 ERA while Chicago counters with Matthew Boyd (9-3, 2.52). Although both rotations have been elite, the host highlighted New York’s edge at the plate (league-best WRC+ vs LHP) and noted both bullpens are scuffling, but Fried’s ability to work deep mitigates New York’s weaker relief corps (5.08 ERA last 7; Cubs 5.25). With the Yankee bats “firing on all cylinders,” he expects them to take the series early.

Chris Welsh took Seattle on the first-five money line despite the juice because he wants to back Bryan Woo and fade Marcus Stroman. Welsh loves Woo’s current form and does not trust Stroman in Yankee Stadium, so he’s betting the Mariners will be in front through five innings before bullpens enter the equation.

Chris Welsh urged fantasy managers not to drop Cam Schlittler after streaming him. The rookie sat 97.9 mph (touched 100) in 5.1 innings versus Seattle, fanning seven. Welsh loved the 38 % CSW on a fastball he threw 50 % of the time and a power slider that hit 94. With a tall frame that creates extension, Schlittler pounded the zone (fastball + slider strikes) and showed a four-pitch mix he can expand once he settles in. Welsh expects the Yankees to keep him in the rotation given their injuries and sees legitimate "strong second-half" upside—close enough to Chase Burns that he’d keep Schlittler on rosters to see how the league adjusts before deciding.

Gary Sheffield Jr said Luke Weaver no longer profiles as a trustworthy late-inning option after coming back early from a hamstring strain. Sheffield called Weaver "a shell of himself," noting diminished velocity and command since the injury and stressing that the Yankees clearly lack a lockdown reliever. Because Brian Cashman is almost certain to shop for a high-leverage arm before the deadline, Sheffield urged season-long players chasing saves to move off Weaver now and instead stash potential trade targets such as Jhoan Duran or Eugenio Suarez-type bats who could shift bullpen hierarchy upon arrival in the Bronx.

Gary Sheffield Jr labeled Edward Cabrera a high-ceiling gamble for contenders, specifically noting that the Yankees are in the mix and could let pitching coach Matt Blake "fix this sinker-slider-changeup guy." Sheffield dismissed the Marlins’ track record of mishandling young arms and argued that Cabrera’s raw stuff—upper-90s sinker, wipeout slider, and a Bugs Bunny change—could flourish in New York’s data-driven development system. Season-long managers in deeper leagues were encouraged to stash Cabrera now, betting on a post-deadline skill unlock and better win potential outside Miami.

Gary Sheffield Jr said the Yankees remain the right side of the AL East coin-flip futures market (+100 compared to Toronto’s +110). His conviction rests on New York’s league-best +105 run differential versus the Blue Jays’ +20, a gap he views as a truer indicator of team quality than the current 2.5-game standings deficit. Sheffield noted the Yankees’ poor record in one-run and extra-inning games as a variance issue that should normalize, especially once the front office patches obvious holes (third base and bullpen) before the deadline. He added that Toronto’s success has been propped up by an inflated home record and that the Yankees’ aggressive deadline shopping signals internal confidence, making New York a buy in the division market.