Best Player Props for Monday's MLB Slate: Lester conquers return to Wrigley

Washington Nationals starting pitcher Jon Lester (34) pitches against the Philadelphia Phillies in the fourth inning at Nationals Park
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Andrew Ortenberg

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I'm an NFL handicapper here at Pickswise who was raised in a household full of sports fanatics. Since I unfortunately never had LeBron James' jumping ability I wasn't able to make it to the NBA, and chose writing about sports as the next best thing. An avid sports bettor myself, I'm excited to get to write about the industry as it gets set to take off across the country. Buckle up. For Andrew Ortenberg media enquiries, please email contact@pickswise.com.
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MLB is back in full swing, and we’ve got another great slate on Monday. It’s a smallish one with only nine games, but there are still plenty of opportunities for value. We’ve had a lot of success lately, including a big mega parlay win last week, and we’re looking for more big wins here. I’ve got two player props which I really like that I’m going to discuss this morning. One of them centers on a big game from Jon Lester in his return to Wrigley. Don’t forget to check what our MLB analysts have backed with side and total picks for all nine games today.

Tim Anderson over 0.5 runs scored (-140)

Line available at publishing at DraftKings

Before we get to Lester, there’s something I like in this White Sox/Twins game. Anderson has been having a great season, and he enters this one hitting .328. He also has a career-high on base percentage right now. Needless to say, getting on base is the name of the game for scoring runs.

He should get on base just fine here. Interestingly, Anderson has had a ton of success against Twins starter J.A. Happ. In his career against Happ, Anderson is an eye-popping 11/19 with a triple and two home runs.

-140 odds means something only needs to have a 58.3 percent chance of cashing to have value. Anderson has scored a run in 20 of the 28 games he’s been in the lineup for this season. That’s a success rate of 71.4 percent. When you combine that with his appealing matchup against Happ, there’s a lot to like here.

Jon Lester over 4.5 strikeouts (+128)

Line available at publishing at DraftKings

Getting this much plus-money here presents some value. Lester has never been a dominant strikeout pitcher, but he was pretty much always a strikeout an inning guy during his time with the Cubs. Oddsmakers were too quick to write Lester off as washed after his abysmal 2020 campaign, and he’s actually been very solid in his first three starts with Washington after starting the year on the IL.

He’s been shaking off some rust, but still has a 2.25 ERA through those three outings. In his most recent start he struck out four, but he had five in the one before that. He’s now getting to face a Cubs offense that ranks fifth in strikeouts per game entering Monday’s action.

Perhaps most importantly, this is a game he’s had circled for a while. It’s Lester’s first trip back to Wrigley Field after six years with the Cubs. He acknowledged this week it’s going to be an emotional game for him, and I think we see his best effort.

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