Everything has been coming up Jeff lately, as I’ve hit three straight best bets and gone six for nine (nice) in September. Let’s keep the good times rolling. For my best bet for Monday (Sept 14th): MLB Predictions, we’re off to Progressive Field in Cleveland, Ohio. Let’s get this money!
Best Bet for Monday (Sept 14th): MLB Predictions
Chicago White Sox vs Cleveland Guardians
Start Time: 6:40 PM EST
I took the Chicago White Sox as a slight dog the other day as my best bet and cashed it – do I dare to roll the dice on them once again, this time as a bigger underdog? It feels risky, but I have to remind myself that this isn’t the White Sox of 41 wins a couple of seasons ago – this team is actually good, with 76 wins already.
Chicago’s opponent tomorrow, the Cleveland Guardians, are a good team as well, only a half-game behind the American League Central-leading White Sox. Plus, the Guardians need this win more than the Sox, as their playoff chances are still in the 50-50 range (Chicago is considered a playoff lock at this point).
However, I think the visitors prevail on Monday. Cleveland is a crummy home team, with the sixth-worst mark in the majors playing on their home turf (36-39). At the very least, Chicago is worth a gamble at plus money.
The Chicago White Sox on the moneyline is my best bet to kick off the week.
Best Bet: Chicago ML (+138)
Best Bet Overall 2026 Record: 141-109 (56%)
Profit (based on $100/bet): $73.61
Return on Investment: 0%
SGPN Daily Content for Sept 14th, 2026
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