Daily Dingers for Friday (August 14th): Best & Most Fun Home Run Bets

I’m still playing with house money in August, but it’s about time to go on another hot run. For my Daily Dingers for Friday (August 14th): Best & Most Fun Home Run Bets, we’re off to Wrigley Field in Chicago, Illinois, and Truist Park in Atlanta, Georgia. Let’s get this money!

Daily Dingers for Friday (August 14th): Best & Most Fun Home Run Bets

St. Louis Cardinals vs Chicago Cubs

Start Time: 2:20 PM EST

You can count on me to cool a player down, as I did to the Chicago Cubs’ Alex Bregman on Thursday by betting on him to hit a home run. After hitting four over the previous two games, Bregman had a dud when I had money on him.

But I’m giving him another shot tomorrow. He has five homers over his past 10 games, and has hit one out in seven career at-bats against Matthew Liberatore, who is starting for the visiting St. Louis Cardinals on Friday.

Best Bet: Alex Bregman (+560)

Arizona Diamondbacks vs Atlanta Braves

Start Time: 7:15 PM EST

I’m playing the matchup game in my next pick, coming from the Arizona Diamondbacks-Atlanta Braves game. It’s a small sample size (eight career at-bats), but the Braves’ Drake Baldwin likes hitting against the Snakes’ Brandon Pfaadt.

The All-Star catcher has a homer in those eight at-bats against Pfaadt with a 40% hard-hit rate. I like our chances tomorrow.

Best Bet: Drake Baldwin (+475)

Bonus Bet: Junior Caminero (+410)

2026 Overall Record: 26-131 (17%)
Profit (based on $100/bet): -($497.00)
Return on Investment: -3%