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MLB Picks Today: Expert Predictions & Best Bets for Monday, August 17, inc. Cubs vs White Sox
MLB

MLB Picks Today: Expert Predictions & Best Bets for Monday, August 17, inc. Cubs vs White Sox

Javan Shouey
Javan ShoueyAuthor
CreatedAug 17, 2026
Reading time4 min

We had an entertaining weekend of MLB action and now must shift focus to the new week and a load of new series. While Monday's board is a bit dry in terms of betting value, I did find three interesting spots worth diving into. Let's take a look at my best MLB best bets for Monday, August 17.

You can also find out our expert MLB picks for all 11 games, including Cardinals vs Reds, Orioles vs Rays, Diamondbacks vs Red Sox, Padres vs Mets and White Sox vs Cubs, as well as Tigers vs Pirates on ESPN at 7:05 pm ET.

MLB Best Bet: Chicago Cubs ML over Chicago White Sox (-155)

Odds available at Bet365 Sportsbook at time of publishing. Playable to -160.

We have a fun series on tap between the teams from Chicago as the Cubs host the White Sox beginning Monday. Both offenses are in terrific form against the respective handedness they will face Monday. In the last 30 days against southpaw pitching the White Sox sit 5th in wOBA with a 121 wRC+. They draw Shota Imanaga, who allowed three home runs and four earned runs across just 4.2 innings in his last outing. Imanaga had pitched well before that start, however, allowing two or fewer earned runs in each of his prior seven starts. On the season, his 3.74 ERA is backed by a 3.81 xERA. The home run ball is his major concern, but he otherwise limits hard contact and rarely issues walks.

Luis Castillo is the scheduled starter for the White Sox on Monday. Castillo was acquired from the Mariners in a trade deadline deal that was aimed to help bolster this White Sox pitching staff. He delivered a shaky first start with the club but is fresh off 7.0 scoreless frames with 10 Ks against the Reds last time out. Despite that strong effort, I would like to see another strong outing before backing the right-hander. Castillo enters play with a 4.96 ERA and 4.63 xERA while sporting a very weak batted ball profile. The Cubs sit 6th in wOBA with a 112 wRC+ against righties in the last 30 days. I favor the Cubs at current pricing.

Read our full White Sox vs Cubs prediction for tonight's Battle of Chicago

MLB Best Bet: Framber Valdez (DET) Over 5.5 strikeouts (+124)

Odds available at FanDuel Sportsbook at time of publishing. Playable to +110.

I have been picking on the Pittsburgh Pirates when they face a competent left-handed starter, and today I am looking to do the same. Framber Valdez is set to draw a start against this Buccos lineup, a lineup that enters this series in poor form against lefties. Across the last 30 days against southpaw pitching, the Pirates sit 23rd in wOBA with an 81 wRC+. Their strikeout rate of 24.9% is the 11th worst mark in that stretch of play. Kyle Harrison struck out 10 Pirates, Sean Manaea recorded 11 Ks and both Jake Bennett and Patrick Sandoval recorded 6. All four of those performances have come within the last two weeks as all of those arms have soared past their respective strikeout props.

Valdez is not a heavy strikeout arm, but he does have the stuff to rack them up. This 5.5 mark is a number he has surpassed seven times this season, including five times with seven or more recorded. Valdez has notched as many as nine strikeouts in a game this season. While mostly a pitch-to-contact arm who focuses on generating ground ball outs, Valdez is able to work deep into games. His sheer volume of batters faced could help us get there in this prime matchup, and I am willing to take a plus-money stab on the over for his strikeout prop.

Get the full analysis of our Tigers vs Pirates prediction ahead of their clash tonight on ESPN

MLB Best Bet: Shane McClanahan (TB) Over 4.5 strikeouts (-128)

Odds available at FanDuel Sportsbook at time of publishing. Playable to -140 odds.

Shane McClanahan is set to be activated off the IL and make a start against the Baltimore Orioles on Monday. McClanahan has battled injuries over the past few years but when healthy he is still a top-end option for this Rays rotation. The southpaw hurler missed just the 15 days required after leaving his last start early with back soreness. He was limited in his rehab outing but should hopefully still see around 70 pitches or so. 

While it may be smart to be cautious with his return, I am willing to take a stab on his strikeout total in a prime matchup. The Orioles are posting a massive strikeout rate against lefties of late, and the absence of both Taylor Ward and Adley Rutschman makes them more susceptible to the strikeout. In the last 30 days against lefties, Baltimore has a 27.0% strikeout rate, the third-highest mark among any team in that stretch. McClanahan ranks in the 61st percentile in chase rate and the 65th percentile in whiff rate this season, suggesting he could see positive regression in the strikeout department from his current 22.2% rate. I understand if you want to steer clear of this prop given the risk coming off injury, but I see some value in this current pricing.

Find out our expert's Orioles vs Rays prediction