This Pro Pick was released to clients on September 07, 2026 at 10:22AM ET.
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Chicago at Milwaukee

September 7, 2026
img2:10 PM Eastern

I had Chicago on the moneyline against Miami two nights ago, and it cashed, 6-5, part of a stretch that's kept this offense rolling into September. The Cubs are 81-63, trailing Milwaukee's pace in the standings, but this afternoon comes down to the arms, not the win column. Matthew Boyd takes the mound at 8-3 with a 4.05 ERA, and even in a shakier turn against this same Brewers lineup last week, allowing three runs, he still worked into the sixth. Milwaukee counters with Robert Gasser, sitting at 4-5 with a 4.57 ERA, about half a run higher than Boyd's number. Chicago's offense outproduces Milwaukee's in OPS and slugging, and against the weaker arm on the mound, that gap is the whole ballgame. Late in the schedule against a Milwaukee offense that hasn't been scoring much lately, the numbers look like where Chicago sits, too. The bigger bets back it up: Chicago is pulling a clear majority of the money on a ticket count barely over a third, the kind of split that tells you where the sharper side of today's market is landing. Boyd over Gasser is the mismatch this price hasn't caught up to. Chicago is the right side on the moneyline this afternoon, and I don't expect Boyd's arm to keep this one particularly close.

2 units on Chicago +113 (moneyline) (risk 2 to return 4.26)
Result:
LOSS
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Chicago Cubs
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consensus consensus
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