Kenny G advised taking Boston at the current –110 pick’em price, arguing the market is giving "too much respect" to Paul Skeens. While acknowledging the rookie’s 2.07 ERA and seven scoreless against Colorado, Kenny pointed out the limitations: Pittsburgh’s bullpen has cratered down the stretch and the offense ranks dead last in slugging. Boston, meanwhile, owns a 41-25 home record, a top-10 bullpen, and sits fourth in MLB runs scored. After sweeping the Orioles, the Red Sox are just 3.5 games behind Toronto and "due for a breakout offensive performance" that could come against the Pirates’ relief corps even if Skeens is sharp early. Kenny summed it up: “You could maybe take Pirates first five, but full-game Boston is the better play because that bullpen edge is massive.”

Cash Out Sports Picks backed the Red Sox on the full-game moneyline. He noted Boston’s post-All-Star surge, crediting an energized top-of-the-order led by prospect Anthony and Alex Cora’s knack for bullpen match-ups. Debuting 6-foot-6 lefty Tolle adds deception against a Pirates lineup that owns seven sub-three-run nights in its last 13. While Paul Skeens is intimidating, Boston’s plan to mix arm angles and disrupt timing plus a 6-4 head-to-head edge convinced the tout that Fenway’s hosts carry the larger margin for error.