Looking for the best Underdog Fantasy MLB picks today? Our Underdog MLB Pick'em predictions for Thursday, May 21, 2026, spotlight two MLB player props worth targeting on today’s action-packed MLB slate. Braxton Ashcraft’s pitching outs and Dustin May’s walks allowed props both come with clear situational edges backed by current form, matchup data, and recent trends. If you are building your Underdog Pick'em entry for today’s MLB slate, here is the full case for where we land on both and why the MLB DFS projections set up the way they do.

What are the Best Underdog MLB Pick'em Picks Today?

Today’s two best Underdog Fantasy MLB Pick'em plays are Braxton Ashcraft over 17.5 pitching outs and Dustin May over 1.5 walks allowed. Both props are supported by matchup data, current streaks, and favorable line construction heading into an action-packed day of baseball. Read below for the complete analysis on each.

 

 

 

Braxton Ashcraft OVER 17.5 Pitching Outs

Ashcraft has done a great job of late helping out the Pittsburgh bullpen, seeing as he’s completed at least 6.2 IP in three straight starts, and in four of his last five. Of course, the lone time he didn’t in recent history was against this Cardinals team, but I expect better things from the Pittsburgh righty today. He’s actually been better on the road than at home this year, and near double-digit winds blowing in at Busch Stadium is a positive for Ashcraft.

Another reason I like Ashcraft to work deeper into this game is that the St. Louis offense has just lacked juice at the plate of late. Over the last two weeks, the Cardinals have had a bottom-five ISO (.121) and a bottom-10 wOBA (.303). If Ashcraft isn’t threatened, the Pirates should let him work deep into this one. Furthermore, over the last two weeks, the Cardinals have the seventh-lowest walk rate (7.3%) and sixth-lowest strikeout rate (19.2%), so they aren’t doing a ton of the two things that can quickly increase a pitcher’s pitch count.

Dustin May OVER 1.5 Walks Allowed

After a rough couple of starts to begin the season, May has actually settled in quite nicely, posting a 2.83 ERA (3.40 FIP) across his last seven starts, albeit with a 9.7 K-BB%. He’s completed six innings in four straight starts, but he’s also walked multiple batters in each of those starts, including issuing two free passes against this Pittsburgh team in late April. His walk rate sits at 10.1% over his last four starts, and this Pittsburgh lineup has been tough on opposing right-handed pitchers in 2026.

In 2026, the Pirates have the third-best wOBA, sixth-highest walk rate, and the league’s best OBP against RHP! They are about league average in the walks department over the last two weeks, but May’s issues with left-handers (.397 wOBA, 10.9 BB%) feel problematic against a Pittsburgh lineup that will feature not one, not two, not three, but likely four left-handed hitters with a double-digit walk rate against RHP in 2026.

 

 

 

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If you have not yet signed up for Underdog Fantasy, there is no better time than tonight. New users who register using promo code ALARM will receive a free pick plus $50 instantly, giving you real money to work with on this slate and every MLB game going forward. Visit fantasyalarm.com/offers to lock in your bonus before the evening games get underway.