“Love is the most important thing in the world, but baseball is pretty good, too.” — Yogi Berra

In today’s Betting Life newsletter presented by Underdog:

MLB Monday: Back the Red Sox in Baltimore?

Watercooler: Closing time for the Celtics.

NHL Playoffs: A +700 goal prop for Game 3.

It’s 5/27. Take it away, Matt LaMarca

Baseball may not be America’s favorite sport anymore, but it will always be America’s pastime. The MLB dates back to the 1800s, and it’s impossible to talk about the country’s history without mentioning baseball. From guys like Ted Williams, Joe Dimaggio, and Stan Musial fighting in World War II to Jackie Robinson breaking the color barrier, baseball intertwines itself in American history unlike any of the other major sports.

On a day like Memorial Day, baseball feels even more American. To honor our country’s fallen soldiers, Major League Baseball will offer up a larger slate than usual. The action gets underway with the Orioles hosting the Red Sox at 1:05 p.m. ET and wraps up with the Mariners vs. the Astros at 9:40. Eight games will take place in between, with each contest paying tribute to the soldiers who gave everything for our country.

Let’s dive into some of my favorite bets for Monday’s slate.

🧦 Red Sox ML at Orioles (+140; BetMGM)

The Red Sox have exceeded expectations to start the year, largely due to the success of their young pitching staff. That includes Cooper Criswell. Not much was expected out of Criswell in 2024, especially after pitching to a 5.73 ERA out of the bullpen last year. However, he’s been outstanding to start the new season.

Criswell has posted a 2.86 ERA across 34.2 innings, and his 3.35 xERA suggests he’s been as good as advertised. He doesn’t have overpowering stuff – his fastball velocity ranks in the second percentile – but he makes up for it in other ways. He’s one of the best control pitchers in baseball, posting a 5.6% walk rate and 105 Location+, and his 49.0% groundball rate ranks in the 75th percentile.

I give Criswell the edge over Orioles’ starter Cole Irvin. His 3.15 ERA looks similar on the surface, but his 4.05 xERA looks significantly worse. His other advanced metrics are also subpar, so he’s a prime regression candidate moving forward.

These two offenses have been pretty even in their current splits – the Orioles have a 99 wRC+ vs. right-handers, the Red Sox 97 vs. southpaws – so I’m happy to roll the dice with the Red Sox as solid underdogs.

More MLB Bets for Memorial Day

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🏀 The Celtics look to punch their finals ticket. Best bets for Monday’s Game 4.

⛳ Davis Riley went off as big as 300-1 at some sportsbooks this week. He lapped the field at Colonial by 5 strokes.

😔 Tragedy also struck the PGA TOUR this weekend. Sony Open winner Grayson Murray passed away unexpectedly at the age of 30.

⛹️‍♂️ How good is playoff Luka Dončić? Well, he’s already accomplished something Lebron and MJ couldn’t.

📉 Anthony Edwards' struggles continued in Game 3. Over bettors are in shambles.

🧱 Speaking of struggling, Karl-Anthony Towns has been throwing up straight bricks from beyond the arc. Dirk Nowitzki would never.

🗽 Let's hear it for New York. The Rangers are now the favorites to win the Stanley Cup.

🎯 Hey babe, wake up. Premier League Darts is on. Seriously, though, this nine-darter by Luke Littler is perfection.

💰 Your daily reminder that time traveling may already be occurring. This insane parlay is one Mavericks’ win away from hitting.

Game 3 of the Western Conference Finals goes off tonight in Edmonton. The Oilers managed a split in the first two games in Dallas and now have home-ice advantage. With the series shifting back to Edmonton, should we expect more goals, or will the goalies stand tall again? Geoff Ulrich has answers below.

Tyler Seguin Over 0.5 points (+110; DraftKings)

Seguin has arguably been the Stars’ most important forward this playoffs. The 32-year-old only has 10 points in 15 games, but he’s playing a variety of roles for Dallas and has been moved back onto a de facto first line with Jason Robertson, which should only boost his chances of landing a point for us today. He’s also been more aggressive when he’s had the puck in these playoffs. The former Bruin is now averaging 3.26 shots on net per game in the post-season, a full shot higher than he averaged during the regular season. 

Both goalies have been great to start this series, but I can't help but think we’ll see a higher-scoring affair between these two teams soon. Regardless, with the price for Seguin to land us a point sitting at +110 now, today feels like a great time to start looking toward his overs. Much like Game 3 between the Rangers and Florida (which saw four goals in the first period), today’s game between Dallas and Edmonton may be the higher-scoring affair we’ve been craving after these two offensive stalwarts spent the first two games in Dallas in more of a feeling out period.

Dylan Holloway Anytime Goal Scorer (+700; bet365)

This price on Holloway looks extra juicy today for a game that should have lots of back-and-forth action. The Oilers winger has already had some great chances to hit the back of the twine in this series, and he’s also averaged four shot attempts over his last three games. The former bottom-six winger is playing alongside Leon Draisaitl at even strength, who continues to be one of the most underappreciated playmakers in the league. 

Holloway’s not a prolific goal scorer but has elevated his play in these playoffs and is getting extra opportunities now because of it. He’s already scored in one game in each of the past two series and should continue to get plenty of run along Draisaitl, who typically plays well over 20 minutes a game. The price here is also a big factor. Holloway is as small as +400 at other sportsbooks but can be had for +600 on FanDuel (a price I’d still play) and is as big as +700 on bet365. It’s a nice opportunity for Memorial Day betting cards if you’re looking to take some swings in the anytime goal department for Game 3.

More Bets for Game 3