MLB Picks Today: Expert Predictions & Best Bets for Monday, June 29, inc. Pirates vs Phillies

After a solid weekend of MLB action, we get some fresh series and a clean slate to do it all again! Let's dive in and discuss my 3 favorite betting angles for Major League Baseball on Monday, June 29.

MLB Best Bet: Pittsburgh Pirates ML (-106) over the Philadelphia Phillies

Odds available at FanDuel sportsbook at time of publishing. Playable to -115 odds

Aaron Nola is not a starting option that I trust currently. The veteran right-hander has allowed 2 home runs in each of his last 3 starts, and he is fortunate to have only allowed 7 earned runs in that span. He has now allowed 17 home runs in 80.2 innings of work, resulting in a 5.58 ERA. Nola has been worse at home with his ERA at 5.82 and opponents hitting .308 against him. He also allowed 9 earned runs to this Pirates lineup in their first matchup. Pittsburgh is still in terrific form, posting the 2nd best wOBA and a 139 wRC+ against righties in the last 30 days.

In that same sample the Phillies lineup ranks 11th in wOBA with a 113 wRC+. They did score 4 earned runs off Braxton Ashcraft in their first matchup with him, but Ashcraft has been a steady option for this Pirates rotation all season long. Through his first 16 starts spanning 96.2 innings of work the right-hander has posted a 3.07 ERA and 2.88 xERA. He ranks among the best pitchers in baseball at generating chases and limiting free passes, and his strikeout upside is immense as well. Ashcraft has tossed 17 innings of 4-run ball in his last 3 outings, and I expect another strong outing in a Pirates win.

MLB Best Bet: Nick Lodolo (CIN) over 2.5 earned runs allowed (+104)

Odds available at DraftKings sportsbook at time of publishing. Playable to -110 odds.

I am willing to bet against Nick Lodolo on Monday. Lodolo is a talented left-hander that has dealt with injuries and inconsistency throughout his career. 2026 has been a disappointing season for the southpaw hurler as he has a 5.59 ERA through his first 46.2 innings of work. Lodolo has even shakier underlying metrics including a 6.04 xERA and .289 xBA that sit 5th and 6th percentile respectively. The Cincinnati starter did pitch better in his last start, tossing 4 scoreless frames against these Milwaukee Brewers, but now he is tasked with a close proximity rematch against that same lineup.

Milwaukee is a unit that has hit left-handed pitching well in the last 30 days. Across that span the Brewers rank 4th in wOBA with a 121 wRC+ and the 5th lowest strikeout rate. Lodolo isn’t a big strikeout arm, so he will have to grind through each at-bat and depend on his defense behind him. Having faced this lineup in his last start, his first time through the order today is essentially the 3rd or 4th time through the order, giving increased familiarity from Milwaukee batters. At plus-money odds this is a bet I cannot pass up on.

MLB Best Bet: Athletics ML (+100) over the Los Angeles Dodgers

Odds available at Caesars sportsbook at time of publishing. Playable to -110 odds.

It is never fun to bet against the Los Angeles Dodgers, but I believe there is value in doing so on Monday. Los Angeles has been slumping offensively against left-handed pitching, and this seems like an opportune time to take advantage of that. Over the last 30 days of play the Dodgers rank 29th in wOBA with a wRC+ of only 70. They haven't scored more than 2 earned runs off any of the lefty starters they've faced in that span. In that same timeframe the Athletics are crushing left-handed pitching, posting MLB's 2nd best wOBA with a 133 wRC+.

Eric Lauer is the scheduled starter for the Dodgers as he is set to make his sixth appearance as a Dodger. He has pitched well so far for Los Angeles, but his underlying metrics are not friendly. His current 4.87 ERA is shadowed by an even worse 5.36 xERA. Lauer ranks 7th percentile or worse in strikeout rate, ground ball rate, and barrel rate, which is worrisome moving forward, especially in a tough matchup like this.

Gage Jump has showcased his elite talent so far for the Athletics, posting a 2.03 ERA in his first 35.1 innings of work. Jump has yet to allow a home run and is fresh off 12 scoreless frames in his last 2 starts combined. His underlying metrics are dazzling so far, including a low walk rate and what appears to be sustainable strikeout success. It is obviously always tough to face the Dodgers no matter their form, but at current pricing I side with the Athletics to win this game.