May 20 MLB Prop Bet Tips & Picks: Freddie Freeman, J.D. Martinez

Last Updated: May 20, 2021

For Thursday, Mike Barner has your May 20 MLB Prop Bet Tips and 5/20/21 MLB Player Prop Bets. All odds were obtained from PointsBet.

Thursday brings a fairly limited slate across baseball, especially if you want to focus your action on the evening set of games. Still, I’ll look to improve on my season record of 2-1 (+0.25 units) with the following three wagers.

Our friends at PointsBet are offering new customers 2 Second-Chance Bets for up to $2,000. Sign up today!

May 20 MLB Prop Bet Tips

Freddie Freeman, Atlanta Braves vs. Pittsburgh Pirates

To Record an RBI (-150)

Wager: 1 unit (win would pay 1.67 units)

Freeman is off to a slow start this season with a .227 batting average — well below his career mark of .293. He’s been pretty unlucky given his .202 BABIP, however, so expect to start turning things around shortly. He’s already shown signs of heating up, going 13-for-41 (.317) over his last 11 games. He’s also recorded 10 RBIs during that stretch, giving him a total of 28 on the season. Freeman will have a favorable chance to drive in another run today against righty Wil Crowe (4.35 ERA) and the Pirates, who have the 10th-highest team ERA in baseball this year.

Marcus Semien, Toronto Blue Jays vs. Boston Red Sox

To Record a Hit (-250)

Wager: 1 unit (win would pay 1.4 units)

Semien has caught fire after a sluggish April, slashing .377/.427/.710 with 13 extra-base hits in May thus far. He’s also hit safely in 15 of 17 games this month, including multiple hits in each of his last three games. Toronto’s leadoff man will have a good chance to get another knock tonight against Nick Pivetta, who’s surrendered over a hit per inning throughout his career while allowing righties to bat .269 against him.

J.D. Martinez, Boston Red Sox at Toronto Blue Jays

To Hit a Home Run (+260)

Wager: 0.5 units (win would pay 1.8 units)

Home run wagers are certainly risky, but I like taking a chance here with Martinez. He’s already gone deep 11 times this season, including in Wednesday’s game against these same Blue Jays. A matchup against lefty Steven Matz is also enticing considering that Matz has been extremely homer-prone lately, allowing 20 dingers across 72 2/3 innings dating back to the start of last season. Martinez also destroys left-handed pitching, as he owns a career .590 slugging percentage versus southpaws, so don’t be surprised if he goes deep again tonight.

After reading May 20 MLB Prop Bet Tips and 5/20/21 MLB Player Prop Bets, step up to the plate and make your MLB bets for May 20:

  • Read the rest of our MLB betting tips for May 20 and beyond.
  • Our friends at PointsBet are offering new customers 2 Second-Chance Bets for up to $2,000. Sign up today!


Mike Barner

Mike started covering fantasy sports in 2007. In addition to The Game Day, Mike has written for RotoWire, Sportsline, Sports Illustrated, DK Live and RealTime Fantasy Sports. In 2018, he was a finalist for the 2018 FSWA Basketball Writer of the Year award. .

Related articles


Get $1,500 in Bonus Bets

5 stars

Bet $5, Get $150 in Bonus Bets or First Bet Safety Net

5 stars

Bet $5, Get $150 in Bonus Bets

5 stars

Get A Bonus Bet Up to $1,000

5 stars

Bet $5, Get $200 in Bonus Bets

5 stars

Get A Bonus Bet Up To $250

5 stars

Bet $5, Get $200 in Bonus Bets Every Day for 5 days!

5 stars

If you or someone you know has a gambling problem and wants help, please call 1-800-GAMBLER.

21+ and present in OH. Gambling Problem? Call or text 1-800-GAMBLER (CO, DC, IL, IN, LA, MD, MS, NJ, OH, PA, TN, VA, WV, WY).

Call 877-8-HOPENY or text HOPENY (467369) (NY).

Please Gamble Responsibly. Call 1-800-NEXT-STEP (AZ), 1-800-522-4700 (KS, NV), 1-800-327-5050 (MA), 1-800-BETS-OFF (IA), 1-800-270-7117 for confidential help (MI).

All betting content on is exclusively intended for audience members 21 years and older who are permitted to gamble in legal states. The Game Day may earn revenue from site visitor referrals to betting services.

Responsible Gaming: Many sportsbooks offer ways to encourage responsible gaming, including the establishment of limits to deposits, spending, and time dedicated to betting.

The Game Day is a TGD Marketing Ltd. endeavor.