Our free MLB parlay picks are out for Monday, September 4th, 2023! Make sure you check our expert MLB parlay picks before the action kicks off.
San Francisco Giants @ Chicago Cubs – 2:20PM ET
My first pick for this game is for the Chicago Cubs starting pitcher Justin Steele. He has been there best starting pitcher this season, and he will be looking to keep the momentum rolling in the opening game of this series against the San Francisco Giants on Monday afternoon at Wrigley Field. If he can finish the regular season strong, he has a potential darkhorse contender to win the National League Cy Young award as he comes into this game with fifteen victories to his name on the season. I look for him to have a quality performance in this game as he tries to pick up his 16th victory of the season here against San Francisco on Sunday. I expect Justin Steele to go over his total strikeouts in the opening game of the series.
My second pick for this game is for the Chicago Cubs to pick up the victory over the San Francisco Giants in the opening game of the series on Monday afternoon at home. Chicago has been playing solid baseball lately as they have shaken off a slow start to the season to get themselves back into a playoff position in the National League Central division in the National League wildcard race as well. Chicago comes into the opening game of this series with a record of 73-64 through the first 137 games of the season. I expect them to pick up a quality victory in the opening game of this series against San Francisco on Monday night, led by an impressive pitching performance from Justin Steele on the mound.
MLB Parlay Pick 
Cubs ML & Steele over Ks
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Colorado Rockies @ Arizona Diamondbacks – 4:10PM ET
My first pick for this game is for the Arizona Diamondbacks starting pitcher Merrill Kelly. It was a rare occasion on Sunday afternoon, when starting pitcher Zac Gallen got lit up by the Baltimore Orioles and now Merrill Kelly will be looking to right the ship for this rotation and have a solid performance against the Colorado Rockies here on Monday night at home. It is fair to say that Merrill Kelly will have a much easier task going up against one of the worst lineups in all of baseball this season, and I expect him to take full advantage of that and have a quality performance here on Monday night. As I look for Merrill Kelly to go over his total strikeouts in the opening game of the series on Monday.
My second pick for this game is for the Arizona Diamondbacks to pick up the victory over the Colorado Rockies in the opening game of the series here on Monday night at Chase Field. With Merrill Kelly getting the baseball for the opening game of the series I think it gives the Arizona Diamondbacks a massive advantage here on Monday night. I expect them to exploit that advantage to the fullest and pick up a quality victory in a much needed victory coming into the first full week of September as they look to get themselves back into a playoff position in the National League. As I look for Arizona and Merrill Kelly to shut down this Rockies lineup, and for the Diamondbacks lineup to put up a crooked number of their own on the board in a comfortable win to open up the series.
MLB Parlay Pick
D-Backs ML & Kelly over Ks
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Minnesota Twins @ Cleveland Guardians – 6:10PM ET
My first pick for this game is for the Minnesota Twins starting pitcher Pablo Lopez. While he hasn’t exactly lived up to the level of play that Luis Arraez has delivered for Miami this season. The trade for Pablo Lopez has still been a somewhat successful one for Minnesota throughout the year. They could really reestablish the fact here if he goes out on the mound here on Monday night in Cleveland and delivers a fantastic performance, as it could go a long way in wrapping up the American League Central division. I expect him to show why they made the right choice by trading for him, as I look for Pablo López to have a quality start here on Monday night and for him to go over his total strikeouts against Cleveland.
My second pick for this game is for the newly acquired Cleveland Guardians, starting pitcher Lucas Giolito. This is Giolito’s third team this season, and he will be looking to prove that Cleveland made the correct choice by picking them up off of waivers after he was released by the Los Angeles Angels last week. He comes into this game with seven victories to his name on the season, and he will be looking to pick up his eighth victory of the year here on Monday night. He is very familiar with Minnesota after spending the majority of his career with Chicago and I expect him to have a quality start in this game because of that. As I look for Lucas Giolito to go over his total strikeouts here on Monday night at home.
MLB Parlay Pick
Giolito & Lopez over Ks
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Milwaukee Brewers @ Pittsburgh Pirates – 6:35PM ET
My first pick for this game is for the former National League Cy Young award winner, Corbin Burnes. He will get the baseball for the Milwaukee Brewers in the opening game of this series against the Pittsburgh pirates, and he will be looking to deliver a quality performance against a team that he has dominated throughout his career. Although he is not putting up Cy Young caliber numbers this season, he has still been consistent for Milwaukee on the year, and he will be looking to be consistent once again as they look to pick up a key victory in the opening game of the series. I expect Burnes to look like his usual self in this one against the Pirates as I have him going over his total strikeouts here on Monday night on the road.
My second pick for this game is for the Milwaukee Brewers to pick up a victory over the Pittsburgh Pirates in the opening game of this series on Monday night at PNC Park. With Corbin Burnes getting the baseball for the opening game of this series I think it gives Milwaukee a massive advantage here in the pitching matchup on Monday night, despite being on the road. I look for them to take full control of this one, as I look for Corbin Burnes to shut down this Pirates lineup and put Milwaukee in a great position to pick up a much-needed victory as they look to extend their lead in the National League Central division coming into the final month of the season.
MLB Parlay Pick
Brewers ML & Burnes over Ks
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Philadelphia Phillies @ San Diego Padres – 6:40PM ET
My first pick for this game is for the Philadelphia Phillies starting pitcher Taijuan Walker. He has been incredible this season, and he has been the best starting pitcher on the staff by far. He will be looking to deliver another quality performance in the opening game of their series against the San Diego Padres on Monday night at Petco Park. Walker comes into this game with fourteen victories to his name on the season and he will be looking to pick up his fifteenth victory here on Monday night on the West Coast. He has been having a quality season as he was racking up strikeouts and I expect that to continue here on Monday night as I have him going over his total strikeouts against the San Diego Padres.
My second pick for this game is for the Philadelphia Phillies to pick up the victory over the San Diego Padres in the opening game of this series here on Monday night at Petco Park. San Diego is usually a tough team to beat at home but with Taijuan Walker getting the baseball in the opening game of this series I have the advantage going to the Philadelphia Phillies in the pitching matchup. I expect them to exploit that advantage to the fullest extent as they look to pick up a crucial victory in the National League wildcard race heading into the first full week of September. As I look for him to pitch Philadelphia to a comfortable victory over San Diego here tonight.
MLB Parlay Pick
Phillies ML & Walker over Ks
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