MLB Best Bets Today May 20

We’ll call it about 15.55 games on the MLB slate for this evening, as the Twins and Guardians will hope to pick up Monday night’s game in the fourth inning and then play Tuesday night’s scheduled game. Mother Nature looks like a factor again in that one and may impact the games in Chicago and Pittsburgh as well. We’ll see how it plays out, but if there is the expectation for a rain delay – and I think Kevin Roth at Rotogrinders is the go-to guy for this type of thing – pitcher prop Unders are not a bad way to approach the weather uncertainty.

We have a few “TBD” on the slate today, as pitcher injuries, the desire to give guys an extra day or two, and other roster shake-ups are starting to become pretty commonplace. Sometimes that can lead to a little bit of value if you can pinpoint who is most likely to start. Sometimes it can be a giant headache.

This article will run Monday-Saturday and I’ll write up a standalone preview for Sunday Night Baseball on Sundays. This year, we’ll also have MLB best bets from Greg Peterson posted with overnight lines.

My tracking sheet is here. For transparency sake, I also have tracking for my three MLB seasons at VSiN (2024, 2023, 2022).

Odds are from DraftKings Sportsbook because they are widely available to readers and because of some of our betting tools. I highly, highly, highly encourage you to shop around for the best lines. Sometimes they will be at DK. Oftentimes, they will not. Do what you can to shop around and get as much bang for your buck as possible.

Feel free to use my opinions and thoughts, as well as our suite of MLB Betting Tools, including the DraftKings and Circa Betting Splits, Steve Makinen’s Daily Ratings, Greg Peterson’s Daily Lines, the 1st 5 Innings Analyzer, and Umpire Stats.

Here are the MLB best bets today for May 20:

Chicago Cubs (-142, 8.5) at Miami Marlins

6:40 p.m. ET

Jameson Taillon and Ryan Weathers are the listed hurlers here, as these two guys both make a second straight start against the same opponent. Taillon is really going in the wrong direction of late, as he’s up to a 4.53 ERA with a 4.61 xERA and a 5.35 FIP in his 49.2 innings of work. He only gave up three runs to the Marlins over six innings in his last start, but all three runs came on solo homers.

Taillon has allowed seven home runs in his last two starts against the Marlins and Mets. He’s allowed nine Barrels over those two outings and now has a 13.2% Barrel% with a 42.1% Hard Hit%. I don’t see any injury indicators from Statcast data like arm angle, release point, extension, spin rate, or velocity, but that is a pretty egregious command profile in his last two starts. Over his last four starts, he has allowed a 47.9% Hard Hit% and a 16.9% Barrel%.

To give up a 66.7% HH% and three Barrels to a Miami offense that ranks 24th in Hard Hit% and 13th in Barrel% is not a great sign from Taillon.

Weathers was a winner for us on Over 3.5 Strikeouts last time out, as he racked up five punchies over five innings. His three primary pitches were sharp, as he only gave up two hits – one was a homer – over his 76 pitches. He had a 31.3% Whiff% on his four-seam fastball, which came in 1.4 mph harder than last season. He generated a lot of weak contact with that and his sweeper. He had 10 swings and misses overall and threw more than half of his three primary pitches in the zone.

Now he gets to pitch in the climate-controlled conditions of home. I have to think we could see a touch more juice on the fastball and probably better grip, so I think those are two positives for him. The Cubs offense seems to be coming back to earth a bit after the hot start. They’re still drawing a lot of walks, but they’re down to 12th in wOBA in May after being 3rd in March/April. They’ve been a league-average offense over the last two weeks.

I’m going to take a shot with the underdog Marlins here. Cubs closer Porter Hodge just hit the IL with an oblique injury. Ryan Pressly and Drew Pomeranz have worked back-to-back days. Brad Keller worked Saturday and Sunday before last night off. Daniel Palencia has worked three of four. I’m also not a fan of what Taillon has done recently. The Fish have won four of five and things are looking up a bit for them after a really rough start to the season.

I’ll also look at Weathers Over 4.5 Strikeouts, as I’d expect him to generate more whiffs pitching at home and to find success with the same things he just found success with against this lineup.

Picks: Marlins +120; Ryan Weathers (MIA) Over 4.5 Strikeouts (-110)

New York Mets (-130, 8.5) at Boston Red Sox

6:45 p.m. ET

The Mets and Red Sox come together with Clay Holmes and Walker Buehler slated as the starters. Buehler hasn’t made a start since April 26 and did not make any minor league rehab starts. He comes into this start with a 4.28 ERA, 3.87 xERA, and a 4.29 FIP, but Fenway Park is not the kind of place that you want to have questionable command.

The fact that Buehler has done well with his contact management skills, but has still allowed five homers over 33.2 innings of work. While his 31% Hard Hit% is strong, his 9.0% Barrel% still shows that there have been some pitches that have leaked out into the middle of the plate. Buehler’s starts have also come against the Guardians, White Sox, Rays, Blue Jays, Cardinals, and Rangers. Those teams rank 21st, 30th, 24th, 19th, 6th, and 27th in wOBA. The Mets rank 9th. It’s a pretty big step up.

Holmes has a 3.14 ERA with a 3.54 xERA and a 3.10 FIP, so the numbers are really strong, but I am seeing several concerning trends. He wasn’t good against the Pirates last time out with four runs allowed on seven hits. He’s allowed three homers in his last two starts after not allowing any in his first seven starts. 

Holmes is up to a 43.4% Hard Hit% now and has had four straight starts north of 40%, including a 60% Hard Hit% in his last start. He’s allowed eight Barrels in his last three starts. He now has five straight starts with a single-digit SwStr%. His average arm angle has been dropping since mid-April, which could be a sign of a bit of fatigue or maybe a little bit of a dead arm. He has thrown 48.2 innings thus far after throwing 63 each of the last two seasons.

Holmes also saw a notable spin rate drops on his slider, changeup, and on the five pitches classified as cutters. I think we could see some of the pull-side contact start to have more of an impact, and it could potentially be in a place like Boston.

I wouldn’t expect a long start from Buehler, which brings some of Boston’s lesser relievers into the mix. I’m looking for some runs here tonight.

Pick: Mets/Red Sox Over 8.5 (-118)

Houston Astros at Tampa Bay Rays (-130, 9)

7:05 p.m. ET

Brandon Walter makes his return to the big leagues in this one for the Astros against Zack Littell and the Rays. Walter had nine appearances over 23 innings for the Red Sox in 2023 and had a 6.26 ERA with a 4.48 xERA and a 4.60 FIP. He actually did a really good job of limiting hard contact in that stint, posting a 24.4% Hard Hit% and a 7.3% Barrel% on 82 batted ball events, but fell victim to the BABIP gods.

Walter was released by the Red Sox during the 2024 season, which he missed due to a shoulder injury. The Astros signed him 13 days after he was let go. The University of Delaware product was once considered a fringe top-100 prospect and maybe the Astros have gotten him to live up to that hype. Over five starts and nine appearances for the Sugar Land Space Cowboys in Triple-A, Walter has allowed 10 runs on 18 hits. Nine of the runs are earned for a 2.27 ERA with a 34/7 K/BB ratio.

The 28-year-old southpaw has a 60% GB% this season, which is a great strategy in the hitter-happy PCL and should be a great strategy at Steinbrenner Field. I backed the Rays 1st 5 yesterday thinking they’d be able to elevate the ball a bit more off of Colton Gordon, since TB has one of the lowest fly ball rates in baseball. They kind of did and hit a few balls hard, but Walter should be able to get them to beat it into the ground. Also, the Rays are 28th in wOBA against LHP at .264 with a .203/.281/.299 slash.

Littell has allowed a .264/.304/.494 slash at home with a .341 wOBA this season, as the move outside has not really helped him much. In general, he’s had command woes, surrendering 13 homers thus far. He comes in with a 4.31 ERA, 4.90 xERA, and a 5.58 FIP. He also has fallen to a 14.8% K%, so he’s not missing many bats this season. That seems less than ideal with a 45.4% Hard Hit% and a 13.8% Barrel%.

It is a small sample size of 56 PA, but right-handed bats in Tampa own a .264/.304/.528 slash against Littell this season. He was a slight reverse platoon split guy last year, but the bigger thing to me is that his home/road splits were staggering, as he posted a 2.90 ERA at home with a .282 wOBA against, but a 4.54 ERA with a .359 wOBA against on the road.

I think moving outside is bad for him and his current command profile. And I’ll take my shot with Walter and the Astros bullpen, especially with Ryan Gusto as a potential piggyback candidate for Walter.

Pick: Astros +110