Daily Dingers for Wednesday (Sept 9th): Best & Most Fun Home Run Bets

Just when it looked like I would never cash a home run prop bet again, Corey Seager came through for me on Tuesday night. Now to get a hot streak going. For my Daily Dingers for Wednesday (Sept 9th): Best & Most Fun Home Run Bets, we’re off to Yankee Stadium in the Bronx, New York, and American Family Field in Milwaukee, Wisconsin. Let’s get this money!

Daily Dingers for Wednesday (Sept 9th): Best & Most Fun Home Run Bets

Colorado Rockies vs New York Yankees

Start Time: 7:05 PM EST

You know it’s been a lost season for New York Yankees slugger Aaron Judge when you realize that September 9th is the first day I’ve bet on him to hit a home run.

But tomorrow is a perfect storm for a now-healthy Judge. The Colorado Rockies are in town, Tomoyuki Sugano is starting, he’s allowed the (tied for) fifth most homers in the majors this season, and Judge has taken him yard three times in just nine career meetings.

Best Bet: Aaron Judge (+300)

Chicago Cubs vs Milwaukee Brewers

Start Time: 7:40 PM EST

Leave it to me to jinx the best hitter in the game, but I don’t think I’ve cashed a home run prop on the Chicago Cubs’ Pete Crow-Armstrong yet this season. That ends tomorrow night in Milwaukee.

Not much analysis needed here – PCA is swinging a hot bat and has homered off of the Brewers’ starter on Wednesday, Logan Henderson, once in three at-bats.

Best Bet: Pete Crow-Armstrong (+320)

Bonus Bet: Rafael Devers (+400)

2026 Overall Record: 33-184 (15%)
Profit (based on $100/bet): -($2,837.00)
Return on Investment: -13%