MLB Best Bets Today May 16
Rivalry weekend continues, as we see a bunch of interleague action plus two games in each league. Our first game starts at 1:10 p.m. ET and our last game starts at 9:40 p.m. ET, so it is a full day of baseball and one that features a wide variety of starting pitchers.
As usual, in the interest of lead time, I’m only considering games that start mid-afternoon or later so that readers have time to digest the info and see if they want to fade or follow. If you want to jump on the early games, see the link below for Greg Peterson’s insights, which are posted the night before.
I’ll be posting my daily best bets Monday-Saturday with a Sunday Night Baseball preview on Sunday, as all the day games make it tough to get something out with lead time out here in Las Vegas. All lines are from DraftKings and are current at the time of publish. Please take the initiative to SHOP AROUND for the best odds. It matters. A lot.
One new offering this baseball season is our Opta AI Player Prop Projections. They are for VSiN Pro Subscribers only, so you can check out our current offers here. Zachary Cohen will be using those projections and his own handicapping to write up MLB player props.
Greg Peterson will have his best bets posted the night before and you can also check out his daily lines to see what looks to be off-market. Steve Makinen has also released his updated Bullpen Betting Systems and DraftKings Splits Systems, plus he’ll have a daily analytics report.
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. Check out our new MLB tools powered by Ballpark Pal: Strikeout Projections, Park Factors, and YRFI Report.
Here are the MLB best bets today for May 16:
Chicago Cubs at Chicago White Sox (-110, 8.5)
7:10 p.m. ET
The Windy City Showdown continues on the South Side, as we get Game 2 of this weekend set. The Cubs kept up their winning ways with a 10-5 decision last night and will look to keep that momentum rolling here today in a matchup of Jameson Taillon and Davis Martin.
Martin is certainly one of this season’s biggest surprises. He was a viable arm last season with a 4.10 ERA and a 4.64 FIP, but his 5.11 xERA was a somber stat to ponder heading into this season. All Martin has done is post over a strikeout per inning with almost a 10% K% bump compared to last year while running a 1.62 ERA, 2.32 FIP, and 3.89 xERA.
Forgive me for being a skeptic, but I can’t really see Martin continuing this pace and he now faces a Cubs lineup that has the second-lowest Chase Rate of any lineup that he has faced. The other one was the Marlins in his first start of the season. Martin has a 4.5% HR/FB% by staying off the Barrel with a lot of contact induced on pitches outside the zone. Per Statcast, his 35.7% Chase Rate ranks in the 89th percentile. He also has an 80th percentile K% and a 92nd percentile BB%.
But a lot of other metrics are concerning. His xBA ranks in the 28th percentile at .261, while he has allowed just a .223 BA. His average exit velo ranks in the 21st percentile and his Hard Hit% ranks in the 18th percentile. On the surface, it looks like Martin has done a really good job of neutralizing lefties, holding them to a .196/.252/.346 slash. But, that comes with a .244 BABIP against. Lefties are underperforming by over 80 points in SLG based on their xSLG against his fastball and by almost 250 points on his changeup, his second-most frequent offering to LHB.
A correction is coming for Martin and I could definitely see that today against a Cubs lineup that is the best he’s faced this season with a .335 wOBA and 115 wRC+.
Taillon has regression signs of his own, as he has a 3.94 ERA with a 4.21 xERA and a 5.66 FIP. Taillon’s given up 11 homers in 45.2 innings, hence the ballooned FIP. He has allowed a 13.3% Barrel%, but only a 35.9% Hard Hit%, so it’s been kind of a quirky year for him. He’s allowed 21 runs this season and 18 have come via the long ball. He’ll probably give up a couple today, but I think the reckoning coming for Martin is a bigger deal.
I’ll play the 1st 5 total here to protect the Cubs position in case they do get to Martin, but the White Sox do the same to Taillon.
Pick: Cubs -109; Cubs 1st 5 Team Total Over 1.5 Runs (-154); 1st 5 Over 4.5 Runs (-110)
Milwaukee Brewers (-126, 8.5) at Minnesota Twins
7:10 p.m. ET
We have an excellent pitching matchup today between the Brewers and Twins. It will be young fireballer Logan Henderson for Milwaukee and crafty southpaw Connor Prielipp for Minnesota. My focus is on a player prop here for Prielipp.
The left-hander has had a tough start to his career from a Whiff% standpoint by having to face the Guardians, Blue Jays, and Mets. All of those teams do a good job of putting balls in play. Despite that, Prielipp still has 21 strikeouts in his 19 innings with just a 9.7% SwStr%. Not only do I think we could get some good numbers on his K props against different lineups moving forward, but I think we have some value on Over 4.5 Strikeouts today.
The Brewers are a pretty good team about putting balls in play and not whiffing, but their 20.9% K% against lefties is over 2% higher than both the Blue Jays and Guardians and just 0.2% better than the Mets. Toronto is the second-most aggressive offense from a Swing% standpoint, so they are very tough to punch out. Prielipp still had four strikeouts in five innings, which is his only start under this total.
What makes Prielipp special is his incredible spin rates on his slider and curveball. His average spin rate on his curveball this season is 3,209 rpm. The league average for starting pitchers on curveballs is 2,576 rpm. Similarly, if we look at his slider at 2,843 rpm, that’s also well above the league average at 2,432 rpm.
Why does spin rate matter? Nearly 11 years ago, Jonah Pemstein wrote about the impacts of spin rate on hitters for FanGraphs. But here’s the most important graphic to note.

As you can see, the higher the spin, the lower the Contact%. It may be tough to read the key, but the blue line is curveballs and the pink line is sliders. Now, obviously hitters and pitchers have evolved over the last decade. Hitters are much better equipped to handle spin. But, just setting a Statcast search at 2,600 rpm, the Whiff% on sliders league-wide for starting pitchers is 39.4%. That’s still over 200 rpm below Prielipp’s average.
If we look at curveballs at 2,800 rpm or higher, the Whiff% is 33.3%. Again, Prielipp’s is much higher than that. If we go up to 3,000 rpm or higher, the Whiff% actually drops to 31.9%. But, Prielipp’s curveball Whiff% is just 18.8% this season, so that’s an area of growth for him. Similarly, his slider at 33.3% is a little lower than what we’d expect, mostly because of his opposition.
Long story short, I think we have a chance to keep a close eye on Prielipp’s strikeout prop over his next few starts, including today.
Pick: Connor Prielipp (MIN) Over 4.5 Strikeouts (-118)





