Our free MLB parlay picks are out for Monday, May 29th, 2023! Make sure you check our expert MLB parlay picks before the action kicks off.
Minnesota Twins @ Houston Astros – 4:10PM ET
My first pick for this game is for the Minnesota Twins, starting pitcher Sonny Gray. He comes into the start undefeated, and he will be looking to keep his undefeated record intact against the defendant World Series champions. He will be looking to pick up his fifth victory of the season in the start and get the Minnesota Twins the victory in the opening game of the series on Monday night. His Earned Run Average is currently under two at 1.82 and he will be looking to further lower that number in this start as well. He comes into this game averaging around 6 1/2 strikeouts per appearance this season. I expect him to go over his total strikeouts in this start on Monday against Houston.
My second pick for this game is for the Minnesota Twins to pick up the victory over the Houston Astros in the opening game of this series on Monday night. They have the advantage of the pitching matchup in this one with Sonny Gray on the mound for Minnesota. I expect them to grab a victory from the defending world champions on the road here on Monday behind a solid start from Sonny Gray. I look for Minnesota to pick up a comfortable victory over Houston with their offense doing just enough to grab them the victory in this one.
MLB Parlay Pick 
Twins ML & Gray over Ks
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Atlanta Braves @ Oakland Athletics – 8:07PM ET
My first pick for this game is for the Atlanta Braves Ronald Acuña. He has been seeing the baseball well throughout the early part of the season and he has been hitting the ball all over the park as well. Now Atlanta will head to the West Coast and open up a series with the worst team in baseball, and Ronald Acuña is likely going to take full advantage of their terrible pitching staff. I expect Acuña to thrive at the plate during this game, and throughout the entirety of the series as well. That is why I expect Ronald Acuña Jr. to go over his total hits in the opening game of this series against the Oakland Athletics on Monday night.
My second pick for this game is for the Atlanta Braves to pick up the victory and cover the spread against the Oakland Athletics here on Monday night in Oakland. The Athletics are on pace to become the worst single-season team in the history of Major League Baseball. I don’t expect to get much better for them in this one against Atlanta on Monday. I look for the Atlanta Braves to pick up a comfortable victory to open up this series, and Ronald Acuña in the rest of the Braves lineup to be the catalyst behind the victory.
MLB Parlay Pick
Braves ML & Acuna over hits
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Los Angeles Angels @ Chicago White Sox – 8:10PM ET
My first pick for this game is for the Los Angeles Angels, Mike Trout. He is having an incredible season up until this point and he will be looking to keep the momentum rolling in game number one of this series in Chicago on Monday night. He is one of the most consistent players in the league, and he has been putting it on display for over a decade now. I expect his productive season at the plate to continue in this one as the Angels look to open up the series with a White Sox with a much-needed victory. I look for Mike Trout’s performance to be instrumental in the outcome of this game in for trout go over his total hits here on Monday.
My second pick for this game is for the Los Angeles Angels to pick up the victory over the Chicago White Sox in the opening game of this series. With guys like Mike Trout and Shohei Ohtani in your lineup, you should be favored to win every game especially when you’re going against a White Sox team that has struggled throughout the early part of the season. I expect the Los Angeles Angels to pick up a comfortable victory in the opening game of this series. I expect Mike Trout and Shohei Ohtani to lead the way for the Angels in this one as well. As I expect Trouts performance to heavily influence the outcome of this game here on Monday.
MLB Parlay Pick
Angels ML & Trout over hits
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Washington Nationals @ Los Angeles Dodgers – 9:10PM ET
My first pick for this game is for the Los Angeles Dodgers to go over their total team runs in this game against the Washington Nationals here on Monday night. Despite losing the finale of their series against Tampa Bay yesterday afternoon, Los Angeles put up 10 runs and looked incredible at the plate. Unfortunately for them their pitching didn’t hold up and they would go on to lose the game. I expect them to have another solid offensive outburst in this game as they open up the series with Washington on Memorial Day evening. I look for Los Angeles to go over their total runs as a team here on Monday night against one of the worst pitching staffs in baseball.
My second pick for this game is for the Los Angeles Dodgers to pick up the victory over the Washington Nationals in the opening game of the series on Monday. The Dodgers have finally gotten it together this season and now find themselves atop the National League west division. Although Washington has exceeded expectations, I don’t expect things to go well for them in this series against Los Angeles on the road in LA. I expect the Dodgers to jump out on them earlier this game and pick up a comfortable victory to open up the series here on Monday night.
MLB Parlay Pick
Dodgers ML & Dodgers over runs
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New York Yankees @ Seattle Mariners – 9:40PM ET
My first pick for this game is for the Seattle Mariners J.P. Crawford. He has been hitting the baseball well throughout the last couple of weeks and I expect that to continue as they open up this series against the New York Yankees. Everywhere you look it seems like J.P. Crawford is hitting long balls out of the stadium as he has had one of the hottest streaks of the season thus far. I look for his productive numbers at the plate to continue in this game against New York on Monday night. That is why I have J.P. Crawford going over his total hits here against the Yankees on Monday.
My second pick for this game is for the Seattle Mariners to pick up the victory over the New York Yankees in this game on Monday night. The pitching matchup in this one favors the Seattle Mariners, as they are going up against Domingo German and he has struggled throughout the early part of the 2023 Major League Baseball season. The Mariners also have the added advantage of being at home for this series as the New York Yankees will be flying across the country after finishing up a home series on Sunday afternoon. I expect Seattle to grab themselves a comfortable victory in this game.
MLB Parlay Pick
Crawford over hits & Mariners ML
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