Ruffolo is on the Cubs -1.5 against Pittsburgh. He trusts Shota Imanaga to post a quality start and thinks Pirates right-hander Mike Burrows is ripe for punishment. While Chicago’s lineup has been in a mini-slump, Ruffolo stressed the overall talent and expects regression to the mean, especially against a pitcher who has struggled with command and home-run avoidance at both Triple-A and in his brief MLB looks.

Eric Pathi said the Pittsburgh Pirates at +185 are his complimentary wager for 8/16/25 because they fit his long-running underdog value system. Pathi reminded listeners that since May 1 there have been 522 MLB games in the +110 to +180 range; blindly backing every one produced a 248-274 record yet still netted +63 units, or $6,300 for a $100 bettor. He stressed that this edge comes strictly from market mis-pricing of dogs—“pitchers have zero to do with baseball betting” in his view—and that the Pirates price lands squarely in the same profitable band. The play is therefore a pure numbers grab, not a matchup-based handicap.

Guy Boston Sports said bettors should back the Cubs on the money line and play their team-total over in Friday’s opener with Pittsburgh. He pointed out that Colin Rea has delivered consecutive quality starts, including six scoreless innings versus St. Louis, and has limited the Pirates to exactly two earned runs over six frames in both prior 2025 meetings. Meanwhile Pittsburgh is opting for a bullpen day with Braxton Ashcraft acting as an opener, exposing a relief corps that has already been worked hard during the club’s 3-7 slide. With the Pirates ranking near the bottom of the league in wRC+ and Chicago returning home where their offense has been far better, he is comfortable laying the current −178 and even prefers the alternative −1 run line plus a Cubs team-total over, expecting Chicago’s bats to ‘pick apart’ the pen all afternoon.

Kenny G said he would still side with the Cubs moneyline (-205) or the ‑1.5 run line against Pittsburgh, even though Chicago’s offense has gone 1, 1, 2, 9, 0 runs over its last five contests. His confidence is rooted in how badly the Pirates are trending: five straight losses, an MLB-worst lineup that ranks last in both runs scored and slugging percentage, and no confirmed starting pitcher, which likely forces a shaky bullpen that sits at a 4.23 ERA into a piecemeal start. Meanwhile Colin Rea (9-5, 4.09 ERA) has handled the Bucs twice already this season—both six-inning outings with exactly two earned runs—giving the Cubs a clear pitching edge. Kenny cautioned this is only a lean and not a pinned play because Chicago’s bats are frigid and the missing Pirates starter could change the market, but he still views the Cubs as the correct side if bettors need early action on Friday’s lone day game.