Free MLB parlay, player prop bets, odds, DraftKings King of the Diamond picks, predictions for Friday, May 23

The Friday MLB schedule is loaded with 16 games and all 30 MLB teams in action. The 2025 MLB home run race is tight, and three of the perennial top contenders — Kyle Schwarber, Shohei Ohtani, and Aaron Judge — all are at the top of the leaderboard. Schwarber and the Phillies will take on the Oakland Athletics at 10:05 p.m. ET, Ohtani and the Dodgers will take on the New York Mets at 7:10 p.m. ET, and Judge and the Yankees will host the Colorado Rockies at 8:40 p.m. ET. Should you target Schwarber, Ohtani, or Judge when making home run prop bets on Friday? 

SportsLine expert Jimmie Kaylor has broken down the MLB odds and just revealed his top picks and MLB player props for Friday. Combining his three picks into an MLB Parlay at DraftKings Sportsbook would result in a boosted payout of +3315 (risk $100 to win $3,315), and would give you five players eligible for the DraftKings King of the Diamond promotion on May 23 (pre-boosted payout is +2215). New users can even take advantage of the DraftKings promo code offering $200 in bonus bets instantly with a $5 wager.

To take part in the DraftKings King of the Diamond promotion, users have to opt into the promotion on DraftKings Sportsbook, then choose between 2-5 players to place in any type of parlay (Same Game Parlay, SGPx) with a “To Hit a Home Run” bet. The parlay is also eligible for a 50% profit boost. ‘King of the Diamond’ is awarded to all MLB players who hit one or more home runs as part of the highest-scoring MLB team (from eligible games) of the day. In addition, check out our best MLB home run picks for Friday and MLB total bases picks.

Kaylor has been profitable as a handicapper across multiple sports since joining SportsLine, and his background as a former college and NFL player gives him a unique perspective when building his fantasy lineups and locking in his online sports betting picks.

Now, here are the Kaylor’s three picks in his MLB home run parlay on Friday:

• Aaron Judge HR (+150)
• Trent Grisham HR (+200)
• Kyle Schwarber HR (+285)

Aaron Judge to hit 1+ home runs (+150)

The Yankees vs. Rockies game is projected to be the highest-scoring matchup on the Friday MLB schedule with an over/under of 11.5 runs. As such, I am targeting two players from the Yankees in my King of the Diamond parlay on DraftKings. The first is Judge, who enters Friday batting .396 with 16 home runs on the season. Judge is a threat to leave the yard in every at bat.

Trent Grisham to hit 1+ home runs (+200)

Grisham is my second pick from the Yankees in my Friday parlay. The left-handed hitting center fielder has a favorable matchup against Colorado starter Tanner Gordon, and he ranks second on the Yankees with 12 home runs on the season. 

Kyle Schwarber to hit 1+ home runs (+285)

Schwarber is tied for the MLB lead with 17 home runs on the season. The Phillies-A’s game also projects to be a high-scoring matchup, which makes Schwarber (and Bryce Harper) very intriguing here. I like Schwarber to homer for the third time in five games here.

Want more MLB picks for today?

You’ve seen some of Kaylor’s MLB best bets for Friday. Now, get spread, total and money-line picks for every game here, all from the model that’s simulated every game 10,000 times. 

Also at SportsLine:
You can also see today’s top MLB picks from expert Matt Severance, who’s on a sizzling 111-58 roll on his last 169 MLB picks. Visit SportsLine to see his best plays for today, all from the expert who’s up more than 17 units. 

Terms and Conditions

Use your Profit Boost Token on a pre-game MLB Home Run Parlay, Same Game Parlay, or SGPx bet & enter to win a share of $1,000,000 in Bonus Bet prizes!

Details:

1. All MLB games starting at 6:00 PM ET or later on Friday, May 23rd
2. Following Opt-In, you’ll be issued one (1) single-use King of the Diamond Profit Boost Token that works on Pre-Match MLB Player Home Runs on 5/23 –King of the Diamond Profit Boost Token is eligible for Parlays, Same Game Parlays, or SGPx bets where all legs are Player Home Runs –Each leg of the Qualifying Bet will count as an entry into the King of the Diamond promotion
3. Profit Boost: 50%
4. Max Bet: $10
5. Min Bet: $5
6. Maximum of 5 Home Run legs (Minimum 2 legs)
7. If your Home Run bet includes a player who hits a Home Run and plays for the highest scoring team of the day, you’ll win a share of the $1,000,000 Bonus Bet pool a. If multiple players from the highest scoring team hit home runs, the prize pool will be split among all customers who bet on any of those players
8. Bonus Bets will be rewarded within 48 hours of the conclusion of the final MLB game on 5/23. Bonus Bets are single-use, non-transferable, non-withdrawable, and have no cash value. Bonus Bets are valid for seven (7) days (168 hours) from the time they are credited to customers’ accounts. Bonus Bet stake removed from payout
9. One Profit Boost Token per customer for this promotion
10. Profit Boost Token expires at the start of the final MLB game on 5/23
11. You must select the Token in your betslip BEFORE placing the Profit Boost Token to apply the promotion.
12. Wagering on this promotion must use funds from your cash balance or DK Dollars. Bets placed with other bonus rewards are void. Cashed out bets and voided bets will void this promotion.
13. Must be 21+, unless otherwise stated and located in 21+ and physically located in AZ, CO, CT, IA, IL, IN, KS, LA (select parishes), MA, MD, ME, MI, NC, NJ, NY, OH, OR, PA, TN, VA, VT or WV. 18+ and physically located in DC/KY/NH/WY.

Ineligible Bets:

• Excludes singles, live bets, progressive parlay, odds boosts, cashed out and voided bets
• Wagers with legs on non-eligible games

PROMOTION REQUIREMENTS AND ELIGIBILITY

The promotional offer is valid between 05/23/2025 at 7:00 AM Eastern Time (ET) and 05/23/2025 at the start of the final MLB game (the “Promotional Period”). Must be physically located in AZ, CO, CT, DC, IA, IL, IN, KS, KY, LA (select parishes), MA, MD, ME, MI, NC, NH, NJ, NY, OH, OR, PA, TN, VA, VT, WY or WV (each an “Eligible Jurisdiction” or, collectively, the “Eligible Jurisdictions”). Must be 21+ years of age or older (18+ if in DC/KY/NH/WY). Any customer who is found to be ineligible to play on DraftKings (i.e., by way of self-exclusion from gambling, restriction due to employment, or otherwise) may not participate in this Promotion and immediately forfeits any bonus rewards which have been awarded under this Promotion.

In addition to the eligibility requirements set forth above and in the DraftKings Terms of Use, to participate in the Promotion, customers must (1) be a registered DraftKings Sportsbook customer with an active account; (2) receive an offer to participate in this Promotion; and (3) opt-in by clicking on the appropriate link or button prior to the start of the final MLB game on 05/23/25.

PROFIT BOOST REDEMPTION

Upon completion of the promotion requirements, eligible customers will be awarded one (1) 50% Profit Boost Token (the “Token”). Token will boost Qualifying Bet profit by 50%. Token valid only on pre-game MLB home run parlay bets on Eligible Games (defined below). Qualifying Bet includes all parlays where each leg is a pregame MLB home run bet (Parlay, Same Game Parlays, Same Game Parlay Extra). Maximum 5-leg parlay (the “Qualifying Bet”). All other bet types are excluded from this Promotion. Cashed-out bets and voided bets will void this Promotion. Bets placed with bonus rewards (including but not limited to Bonus Bets, Odds Boosts/Surges, Profit Boosts, etc.) are not valid. Token expires at the start of the final MLB game on 05/23/25. Qualifying Bet must be placed using cash from your cash balance or DK Dollars. Maximum Qualifying Bet $10. Minimum Qualifying Bet $5.

ELIGIBLE GAMES

Only MLB games scheduled to start at or after 6:00 PM Eastern Time (ET) during the Promotional Period (the “Eligible Games”) qualify for this Promotion. To be eligible, the game must be completed within 36 hours of the original start time and made official (in accordance with our broader house rules). Games that are postponed more than 36 hours of the original start time or canceled will not count toward fulfillment of the Promotion requirements and will be considered ineligible.

PROFIT BOOST LIMITATIONS

Profit Boost Tokens are single-use and have no cash value. Token must be applied BEFORE placing bet. Profit boost is calculated on and only applies to net winnings (total payout less Qualifying Bet amount). Subject to any maximum bet limitations, there are no restrictions on the funds a customer will receive if their bet wins. Profit Boosts may not be combined with other bonus rewards and may not be eligible for use on all promotions and/or betting markets.

HOMERUN & HIGHEST SCORING TEAM BONUS PRIZE POOL

Qualified customers who place a Qualifying Bet on a player who hits a home run and plays for the highest scoring team during the Promotional Period using their Token will receive an equal share of a $1,000,000 bonus prize pool. The bonus prize pool will be paid out as one (1) Bonus Bet per customer.

For example, if New York is the highest scoring team for the Promotional Period and 100,000 customers opted into this Promotion and, using the Token, placed a Qualifying Bet on a New York player who hit a home run, each of those 100,000 customers would receive one (1) $10 Bonus Bet ($1,000,000 ÷ 100,000 = $10). Bonus Bet amounts will be rounded to the nearest whole dollar. Bonus Bets will be issued within 72 business hours following settlement of the Qualifying Bet. Qualifying Bets will be settled in accordance with outcome of the event for which they were placed.

If multiple players from the highest scoring team hit home runs, all customers who placed a Qualifying Bet on any such player will be eligible for a share of the prize pool. The total prize pool will be divided equally among all qualifying customers, regardless of which eligible player they bet on.

In the event no players from the highest scoring team hit a home run, the prize pool will instead be awarded based on players from the next highest scoring team during the Promotional Period. This process will continue until a team with at least one player who hits a home run is identified.

In the event two or more teams tie as the highest scoring teams, the prize pool will be split evenly among eligible customers who placed Qualifying Bets on players from any of the tied teams.

BONUS BET LIMITATIONS

Bonus Bets are single-use, non-transferable, non-withdrawable, and have no cash value. Bonus Bets are valid for seven (7) days (168 hours) from the time they are credited to customers’ accounts. Customers can choose when to use Bonus Bets and must select the Bonus Bet in their betslip before placing a wager. Failure to use a Bonus Bet before expiration will void the reward. Payouts from Bonus Bet wagers will be transferred to the customer’s cash balance and do not include the Bonus Bet stake. Ex: If a $10 bonus bet is placed at +100 odds and wins, only the profit of $10 will be credited to the customer’s account. Bonus Bets may not be combined with other bonus rewards and may not be eligible for use on all promotions and/or betting markets.

GENERAL TERMS

Limit one (1) redemption per customer. See DraftKings Sportsbook Terms of Use for information and limitations on wagering. Reward substitutions or changes will be made in DraftKings’s sole discretion. Each customer will be notified when they have received an award by (1) a bell notification (this is a notification that displays as a bell icon on the home page of the DraftKings Sportsbook app and website that can be clicked on to view short confirmation copy and terms) and/or (2) an automatically triggered email if the customer successfully entered the promotion and completed the promotion requirements. Whether a customer has committed abuse of this Promotion, violated the Promotion Terms or DraftKings Terms of Use, will be determined by DraftKings in its sole discretion, for any reason or no reason at all. Should you wish to cancel your participation in this promotion at any time, please contact customer experience at [email protected]. Upon cancellation, you may withdraw any remaining funds deposited in connection with this promotion subject to DraftKings Terms of Use. Any wager placed on DraftKings Sportsbook in connection with the promotion cannot be rescinded once it has been placed. However, any applicable bonus rewards in your account shall be void, subject to forfeiture, and may not be transferred or withdrawn. All promotions are subject to the DraftKings Terms of Use and Privacy Policy. By accepting any bonus rewards, registered customers agree to abide by the terms and conditions of this Promotion. Promotional offer is subject to regulatory approval. Void where prohibited by law. DraftKings account holders are responsible for any and all local, state, or federal taxes. DraftKings is not liable for computer or program malfunctions, nor for errors in bonus rewards. DraftKings reserves the right to exclude or remove certain customers from this Promotion, as well as the right to withhold bonus rewards if you have violated or attempted to violate the Promotion Terms or DraftKings Terms of Use, including but not limited to sharing account credentials with other individuals, placing wagers on behalf of other individuals, circumventing DraftKings age and location verification procedures, and abusing the DraftKings Platform, the Services, or any bonuses, the refer-a-friend program, or any other offers or promotions, including this Promotion, in any way.

If physically located in PA, this Promotion will comply with subsection §813.3 regarding cancellation in this Promotion by a customer. If in NY, if a customer is dissatisfied with any resolution between the customer and DraftKings, the customer may then submit an inquiry with the New York State Gaming Commission.

See DraftKings Terms of Use for information on eligibility for creating, using, and funding an interactive gaming account. DraftKings reserves the right to suspend, modify, and/or cancel this Promotion for any reason in its sole discretion. If you or someone you know has a gambling problem, help is available. Call 1-800-GAMBLER.