May 19-25 Fantasy Baseball Expert Picks: Best Matchups, Streaming Options and More

We have one week until Memorial Day. That's often a checkpoint in the season in which it's said that we can start believing the stats and records that we are seeing from players and teams. With more clarity on who these entities actually are, we can make more confident determinations about what to expect for the rest of the season, though there's still a long way to go.

In the world of fantasy baseball, the grind never stops, and there are daily/weekly decisions to be made from now until October. To help you prepare, Morgan Rode and Daniel Hepner answered five questions in advance of another week of fantasy baseball.

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1. Give us a team with good matchups this week.

Daniel: I talked about the Cubs last week, and the good times look like they could keep rolling. After taking two of three from the Marlins and winning both against the White Sox through Saturday, Chicago now plays three more against Miami and three against Cincinnati, though all six are on the road.

Next week, they will have six games against the Rockies and Reds, so there are more good matchups ahead; Chicago players are good streamers for the next few weeks.

Morgan: I also like the Cubs again this week, but will also mention the Phillies. They play the Rockiers and Athletics this week. Of the probable pitchers for opponents so far, only one has an ERA under 4.00. Philly doesn't have a ton of streaming options, but the matchups are right for every player to go off.

2. How about a few offensive players who are available in fantasy leagues and might be set up for success?

Daniel: Sticking with the Cubs, Miami has a bad pitching staff, while Cincinnati is more average. Chicago hitters are decent bets this week. The players who are widely available and have been in the lineup most are first baseman Michael Busch and catchers Carson Kelly and Miguel Amaya.

Morgan: I like Angels' Zach Neto in matchups against the Athletics and Marlins. St. Louis' Ivan Herrera takes on Detroit and Arizona, but adding and utilizing him is more to do with his strong fantasy showing so far.

3. Do you have any pitchers with a good matchup or two who could have a good week?

Daniel: The Brewers and Yankees both have a week of matchups against bottom-10 offensive teams. Milwaukee faces Baltimore and Pittsburgh (four games); Quinn Priester and Chad Patrick might be in line to face both teams once. New York matches up with the Rangers and Rockies, though the latter games are at Coors Field, hurting the pitchers. Will Warren looks like the one guy who will get a start against each team.

Morgan: Cubs' Ben Brown could make starts against the Marlins and Reds this week - I love both of those matchups. Pirates' Mitch Keller has favorable matchups against the Reds and Brewers, but might be limited because of his own team's struggles.

4. Give us a trade target who is worth exploring if their owner is getting antsy.

Daniel: I love upside, so I'm interested in finding stars who have struggled but have that top-level ceiling. A lot of players can fit that description, so it's more about targeting a position you need or guys you think have a reason to bounce back.

Baltimore shortstop Gunnar Henderson and catcher Adley Rutschman were both drafted near the top of their position and have disappointed greatly. Henderson is hitting .257 with six homers, nine walks, and 46 strikeouts. Rutschman is batting .215 with four homers. Those underwhelming numbers might allow you to buy low on a team that has a recent history of good offensive stats.

Morgan: I'd look into trading for Willson Contreras. He should be eligible at first base and catcher, which is super valuable for fantasy purposes. Contreras is outside the top 10 amongst fantasy first basemen, but is a top-10 fantasy catcher. See if you can add him and add depth or a daily starting piece at 1B and C.

5. What's your best piece of advice for this week?

Daniel: I said in the intro that we can start to believe what we're seeing, but a lot will still change during the season. Take into account what we knew before this year, what we've seen in 2025, and the best projections moving forward, and form your opinion based on all those data points, not just what less than 50 games have told us.

Morgan: Continuing with the fourth point in mind, we're far enough into the season to have opinions on most fantasy players. Now is the time to buy low on struggling players, or consider selling high on red-hot players who cannot sustain their current numbers.