Kenny G labeled Chicago’s –230 money-line as a potential ‘lock of the day’. He trusts Matthew Boyd, who carries a 2.89 ERA and has not allowed more than two earned in any of his last three starts, plus the Cubs’ fifth-ranked bullpen (3.25 ERA). Chicago’s offense, second in MLB runs and third in average, is overdue for a breakout after a brief slump and now draws rookie Mike Burrows (5.00 ERA) and a 4.05 Pirates pen. Pittsburgh ranks 29th in runs and dead-last in slugging, and is 10-23 on the road while cashing an MLB-best 21-10-2 to the under away, highlighting their lack of scoring punch. Kenny expects the Cubs to ‘wake up’ at Wrigley and is willing to eat the chalk rather than gamble on the run line.

Cash Out Sports Picks advised taking the Pittsburgh Pirates moneyline at what he called a coin-flip price because Paul Skenes is pitching like one of the best arms in baseball. Skenes owns a 1.88 ERA, 0.84 WHIP and .173 opponent average, allowing two runs or fewer in 13 of 14 starts. Over his last 22.1 innings he has surrendered just one earned run on nine hits, and his road ERA is an even stingier 1.19 across 45.1 innings. Chicago counters with rookie Cade Horton (4.11 ERA, 1.30 WHIP), a solid but far less dominant option. The tout stressed that chances to back a starter this hot at near-even odds are rare, making Pittsburgh the play.

Kenny G said he is willing to lay the small price on the Cubs at –110, even though Paul Skenes owns a 1.88 ERA and has not surrendered more than one earned run in any of his last five starts. He pointed to three things that swing the matchup toward Chicago: (1) the Cubs are 20-9 at Wrigley this season while Pittsburgh is 9-22 on the road; (2) Chicago’s bullpen ERA has climbed all the way to sixth-best in MLB, giving Cade Horton far better late-game support than Skenes will get from a Pirates relief corps sitting at 4.10; and (3) the Pirates lineup is 29th in runs and slugging, scoring two runs or fewer in five of their last seven, so even a solid Skenes effort may not be enough. Horton’s 4.11 ERA has come against soft opponents, but Kenny expects him to be “at least decent” versus an anemic Pittsburgh offense. With a pick-em price, the superior pen and home field give Chicago the edge.

B Wade backed Paul Skenes to stay under 1.5 earned runs against Chicago. The rookie has allowed 0 or 1 earned in six straight, doing it against legit offenses (Mets, Phillies twice, Brewers, Diamondbacks, Astros). Versus the Cubs he’s been hit-or-miss—three of five prior meetings went over—but that was before his current groove. Skenes owns a 1.88 ERA yet sits 4-6 because of scant run support, so Wade expects him to continue bearing down and limit Chicago to one or fewer.

The tout joked about Garrett Crochet’s name but loved Cody Bellinger’s 4-for-5 (.800) mark against him, plus a current 9-of-10 game hit streak. He called it another solid hit-record prop.

Guy Boston Sports advised taking Andrew Heaney under 5.5 hits allowed at -150 on DraftKings for Thursday’s Pirates-Cubs matchup. Heaney has stayed below this line in 8 of his last 10 starts, surrendering only 4.7 hits on average, and in 11 of 13 outings overall this season (85% hit rate, 4.54 hits per game). The host noted that even in an April 29 meeting with these same Cubs, a 9-0 Pittsburgh defeat, Heaney gave up just five hits to narrowly cash the prop. The left-hander ranks in the 74th percentile for batting average allowed and the 91st percentile in BABIP suppression, evidence that opponents struggle to square him up despite an ordinary strikeout rate and ERA. Historical data backs it up as well: Heaney held opponents to this number 68% of the time in 2024. Chicago’s season-long splits versus southpaws look strong, but the offense has cooled sharply—over the last 30 games their batting average against lefties has fallen from .252 (9th best) to .228 (20th), with a hard-hit rate that sits just 23rd in MLB. Given Heaney’s consistency and the Cubs’ recent slide, Guy Boston Sports feels comfortable laying the juice on the under.

Because the Cubs are –205 on the moneyline, Kenny G prefers taking Chicago at –1.5 runs for plus money (+106 to +112 depending on the book). He likes the matchup: Jameson Taillon is 6-3 with a 3.54 ERA and has allowed two earned runs or fewer in four straight, a span in which the Cubs are 4-0. Chicago backs him with the sixth-best bullpen in MLB (3.31 ERA) and an offense that sits second in runs, third in batting average and fifth in OBP, even if it has cooled the last week. Pittsburgh counters with Andrew Heaney, who was lit up by the Cubs on April 28th (4.2 IP, 4 ER, 2 HR) and now faces them at Wrigley where Chicago is 20-9. The Pirates are just 9-22 on the road and 29th in runs and slugging. Kenny worries the Cubs could top the 7.5-run total on their own, making the run-line his preferred play.