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MLB Picks, Predictions Today: Jon Anderson’s Best Bets for Monday, July 20

MLB Picks, Predictions Today: Jon Anderson’s Best Bets for Monday, July 20 article feature image
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Jun 12, 2026; Milwaukee, Wisconsin, USA; Milwaukee Brewers pitcher Jacob Misiorowski (32) is doused with Gatorade by outfielder Garrett Mitchell (5) after pitching all nine innings of a 6-0 win over the Philadelphia Phillies at American Family Field. Mandatory Credit: Michael McLoone-Imagn Images

Welcome to The Leadoff, a daily column featuring our top expert’s MLB picks, predictions and best bets for today’s slate.

With Sean Zerillo making significant changes to the structure of Opening Pitch, we thought we could use another similar daily piece breaking down a few of our favorite bets on the day’s top games.

Each day, Monday through Sunday, one of our top staff members will provide news, notes and betting analysis on that day’s group of games.

Jon Anderson has that job for Monday, July 20.


MLB Picks, Predictions Today

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  • Pittsburgh Pirates Moneyline
  • Pirates vs Yankees, Over 8
  • Toronto Blue Jays Moneyline
  • Rays vs Blue Jays, Under 7.5
  • Dodgers vs Phillies, Under 8
  • Boston Red Sox Moneyline
  • San Diego Padres Moneyline
  • Padres vs Braves, Over 9
  •  Jacob Misiorowski Under 8.5 K's
  • New York Mets Moneyline
  • Jameson Taillon Over 2.5 ER
  • Jack Flaherty Over 2.5 ER
  • Giants vs Royals Over 10.5
  • Nationals vs Rockies Over 12.5
  • Seattle Mariners Moneyline


Pirates vs Yankees Picks

Pirates Logo
Monday, Jul 20
7:05 p.m. ET
SportsNet PT
Yankees Logo

The Pirates are basically even money lined up against the Yankees in New York City. Who would have seen such a world?

Braxton Ashcraft starts this one for the Buccos. The All-Star second-year man has been one of the game's biggest breakouts this year, and everything under the hood checks out.

Ashcraft has a 28% K%, a 6% BB%, and a 44% GB%, limiting hitters to a .282 xwOBA. He's geared up to be one of the biggest pieces in this Pirates second-half playoff push.

However, it's a tough spot for them against a tough lefty in Ryan Weathers. The Pirates have struggled against lefties this year with a .713 team OPS.

It's a different lineup than the one they've been rolling out this season, since lefties Oneil Cruz and Spencer Horwitz are on the IL. And Pittsburgh has seen the incredible rookie debut of Esmerlyn Valdez, who was probably the best hitter in the minor leagues against left-handed pitching. Every bit of that has carried over to the Majors.

I think we're getting some value on the Bucs at +100 right now. Nick Gonzales has been on a heater in July, and they have a lot of players in here that can make contact and make life tough on lefties.

Plus, the big ballpark upgrade for them going from PNC Park to Yankee Stadium will be critical here. I like backing Ashcraft and this Pittsburgh lineup that is a lot better suited to hit lefties than they have been all year.

Additionally, I'm taking the over.

The Pirates bullpen is a big problem, and I think this Yankees offense is going to wake up. We've seen some positive signs of late, and we're wondering if the Pirates want to take it a bit easy with Ashcraft at this point in the season, as he's nearing a career high in innings pitched as a starter.

So I like the Bucs to score 4-6 runs here, and I think the Yankees can add a few, even if it takes until late in the game.

Picks:

  • Pirates Moneyline (+101)
  • Over 8 (-103)

Rays vs Blue Jays Picks

Rays Logo
Monday, Jul 20
7:07 p.m. ET
RAYS
Blue Jays Logo

Let's talk about Rays' pitcher Nick Martinez.

The man is eighth in baseball among qualified starting pitchers in ERA at 2.26, yet his 14.5% K% is ranked 61st. That doesn't match up and is a completely unsustainable ERA for Martinez, even when you factor in whatever magic the Rays have up their sleeve.

This does seem like a good matchup for Martinez, since the Blue Jays do not strike out, but they don't hit the ball hard and rarely hit the long ball.

And that's exactly what Martinez specializes in. The Rays bullpen is ranked third in the league per our BARTOLO tool, and they are one of the best-managed teams in the league. So this shapes up pretty well for their general style.

On the other side, we have Dylan Cease for the Jays, who ranks second in the league in strikeout rate (behind Jacob Misiorowski).

So these two pitchers couldn't be much different. If you're into baseball data at all, you know the most important predictor of pitching success is strikeouts. Cease's strikeout rate is way more than double the rate of Martinez, and I just can't shy away from that in the betting world.

I do think the Rays can limit the runs here.

I think we'll see a low-scoring affair, but through two very different means. Cease gets the strikeouts, Martinez gets the outs on balls in play.

I'm taking the Blue Jays at -142 and I'm taking the under 7.5. I don't believe in either offense; both clubs are near the lowest in the league in home runs, so we're feeling pretty good about betting unders when either of these teams show up.

Picks:

  • Blue Jays -140
  • Under 7.5 -114

Dodgers vs Phillies Picks

Dodgers Logo
Monday, Jul 20
7:10 p.m. ET
ESPN
Phillies Logo

The Dodgers continue their east coast road trip, heading down the road to Philadelphia after a doubleheader in NYC.

They've moved Emmet Sheehan back to make this start, and he'll square off with Phillies' ace Cristopher Sanchez.

I like both of these pitchers in this spot, even though Sanchez is down right now. He finished with two bad starts away from Philly, and then took the loss in the All-Star Game in front of the home fans.

But we're back to normal business now, and Sanchez has been untouchable at home. He has a 0.86 ERA at home this year (on the road, it's 4.97), along with some of the wildest home/road splits you'll ever see.

Sheehan is a second-half buy. His 27% K% is strong, and his 7.4% BB% is equally so. A 19% K-BB% doesn't make sense with a 4.81 ERA. He'll have to avoid the big bats of Kyle Schwarber and Bryce Harper, but I believe in him.

I'm on the over in strikeouts for both names, and I don't think we see more than a handful of runs here against these two loaded-up pitching staffs. I think this game would be perfectly fine at under 7.5, but we're getting under 8 at even money.

Load up!

Pick: Under 8 (-104)


Orioles vs Red Sox Picks

Orioles Logo
Monday, Jul 20
7:10 p.m. ET
MASN
Red Sox Logo

Payton Tolle is one of the more talented pitchers in the league, posting a 14.2% SwStr% and a 31.4% Ball%.

To interpret those stats for you, it means that he's throwing a ton of pitches in the strike zone while getting a bunch of whiffs at the same time. That's a really tough thing to do.

Tolle is a special talent, and this is just his rookie year. His four-seamer is awesome, and he's developed a cutter and curveball to complement it this year.

His problem is the long ball, but any time he gets some good luck on that, he's been unbelievable. The Orioles matchup is massive for him, since the Orioles' SLG is just .381 against lefties this year.

Boston's offense has come to life, and it gets a favorable matchup with a hittable righty in Shane Baz.

Plus, this game takes place at Fenway, which sets up very nicely for the Red Sox in this spot.

I think you're going to see Tolle develop into a top-tier starter in the next year or so in Boston. He and Garrett Crochet will be a ridiculous 1-2 punch for this squad as we move forward, and I think the time is now to bet on him.

Give me Tolle for six strong innings and a Red Sox win.

Pick: Red Sox Moneyline (-142)


Padres vs Braves Picks

Padres Logo
Monday, Jul 20
7:15 p.m. ET
BravesVsn
Braves Logo

The Padres had a huge run-scoring series in Kansas City, coming off of 19 runs scored yesterday.

Now, they stay away from home for this series as they go into Atlanta, which that's a big advantage for the Padres lineup. They have a team .650 OPS at home — almost 60 points lower than what it is on the road. They've also hit 46 homers at home and 60 on the road.

So we like the buy-low prices on the Padres when they get away from Petco Park. And tonight, they'll face Braves' pitcher Bryce Elder and his 19.8% K%. The Braves are also missing big names in the bullpen right now. Robert Suarez is on the IL, while Dylan Dodd and Dylan Lee are projected to be unavailable due to workloads this past weekend.

JP Sears is not a pitcher you can feel confident betting on, and he'll go against the Braves for this one. However, the Braves are not an impressive lineup against lefties, going for a .710 OPS against lefties this year, and it's down to .680 since June began (around the time they lost Acuna again).

I'm thinking we're getting some run-scoring in this one, and I really like the Padres as a road underdog.

Picks:

  • Padres Moneyline (+120)
  • Over 9 (-120)

Brewers vs Mets Picks

Mets Logo
Monday, Jul 20
7:40 p.m. ET
BREW
Brewers Logo

Jacob Misiorowski makes his first appearance since July 7. That's almost two weeks without seeing the Cy Young front-runner. And the Brewers have to be spinning their wheels here.

They're an overwhelming favorite to win the NL Central after that huge first half they had. The rotation is in a bit of turmoil here, but they have a ton of padding here to take it easy and focus more on October than other teams can.

What I'm guessing will happen is that they'll take it easy with Misiorowski's workload, and I also think they'll have him consider bringing that fastball velocity down a bit.

He has clearly been out there chasing league records and stuff on the radar guy. He did not throw this hard in previous years, even though he was probably capable. So I think that ends here as they shift their focus to long-term health for their best player in this second half. I think Misiorowski fade bets are in full force in this one.

On the other side is the revenge game for Mets' ace Freddy Peralta, who faces a lineup that is about league average. The Brewers' strength is not the lineup. So with a little bit more motivation from Peralta, he could do pretty well here.

Not only that, he's pitching for another contract in this second half on his one-year deal with the Mets, who have already turned the page to being sellers at the deadline.

This is a bit more "narrative street" than I usually like to do, but give me the Mets here! They're at +157 on the moneyline on the road, and there's more than enough here for me to think this one should be in the +120 neighborhood.

Picks:

  • Jacob Misiorowski Under 8.5 K
  • Mets Moneyline +157

Giants vs Royals Picks

Giants Logo
Monday, Jul 20
7:40 p.m. ET
ROYL
Royals Logo

There's something strange going on lately with the O/U lines in Kansas City.

The Padres just finished up a series there where there were 13, 7, and 21 runs scored in the three games. And tonight we see the O/U at 10.5, which is very high.

It seems extra bloated when you see that the Royals have their most reliable starter, Michael Wacha, on the hill. Wacha brings in a 3.77 ERA  this year, and it's at 3.21 at home. He has allowed just 14 homers in 19 starts this year, powered by his changeup that is so hard for hitters to get the barrel on.

Wacha will get to go up against a Giants offense that has struggled to score runs. They are better on the road (.740 OPS vs. .699 at home), but it's far from an imposing lineup.

On the other side is Trevor McDonald, who comes into this game with a 5.02 ERA. He's given up 15 of his 37 MLB earned runs this year in two starts. So, outside of two major problem starts, he's been pretty good at limiting damage, mainly generating ground balls, and has only given up just six homers in 13 starts.

What we have here are two pitchers who excel at limiting homers and two lineups that have a tough time really punishing pitchers, most of the time.

And yet we get the 10.5 O/U? I expected it to be nine. So I like this under a whole lot.

Pick: Under 10.5 (-118)


Tigers vs Cubs Picks

Tigers Logo
Monday, Jul 20
8:05 p.m. ET
MARQ
Cubs Logo

It's a Wrigley winds game as Jameson Taillon hosts Jack Flaherty. Two pitchers we have seen a lot of over the years, and two guys who can certainly give up some runs.

The O/U here is jacked up to 11.5. And that has a lot to do with the weather factor.

detroit-tigers-vs-chicago-cubs-mlb-projections-prediction-pick-odds-wrigley-field

We have projected winds blowing out above 15mph and both of these pitchers have ground ball rates below 35%. If those winds are ripping like expected, there will be home runs in this one, as a good amount of balls are going to be put into the air against these two veteran pitchers.

I'm always hesitant at these 11.5 Wrigley lines, though. The winds are guaranteed to be a factor, and if the wind forecast was reversed, you'd see this total 2-4 runs lower. But I've rarely seen run projections like this and the pitchers give you very little confidence.

What we can do is just fade both pitchers. Maybe the game won't get to 12, but I think the pitchers are going to give up runs, one way or another.

Picks:

  • Jameson Taillon Over 2.5 ER (-148)
  • Jack Flaherty Over 2.5 ER (-150)

Nationals vs Rockies Picks

Nationals Logo
Monday, Jul 20
8:40 p.m. ET
NATS
Rockies Logo

The Nationals' build has turned Nationals Park into a hitters' delight. No park has seen more runs scored in it this year than the one in DC. The Nats can hit, and they cannot pitch well.

Tonight, we're getting two lefties doing battle in this one, and it's an underwhelming bout featuring Andrew Alvarez for the Nationals and veteran Kyle Freeland for the Rockies.

Both clubs hit lefties well, relatively. The Nationals are first in the league in OPS against lefties, and the Rockies haven't been as bad as you thought they'd be with a .700 OPS. The kicker here is that the Rockies will see at least half of this game against one of the league's worst bullpens.

It's about as good of a spot for run-scoring as you'll see. The slew of pitchers you're getting in this game will be Triple-A quality at best.

I think a 12.5 O/U is warranted here, but I doubt most of these books are going to go there. So the current 11.5 line is perfectly fine with me.

Picks: Over 11.5 (-120)


Reds vs Mariners Picks

Reds Logo
Monday, Jul 20
9:40 p.m. ET
SEAM
Mariners Logo

Mariners' hurler George Kirby is facing a weak Reds lineup that is coming from Coors Field (one of the best hitting environments in the league) to Seattle (one of the toughest).

The Reds are slashing just .234/.307/.412 since June began, with a team 26% K%, which in case you couldn't tell, that's terrible.

Kirby hasn't had a studly season, posting a 3.76 ERA with a 1.31 WHIP. Those aren't the ratios you thought you'd get from Kirby this season, but at least he's staying healthy and posting a decent 16% K-BB%. I like his chances here at home with what we just mentioned about the Reds lineup. And my projection model agrees.

I have Kirby for 6.4 strikeouts in this spot, which is well above his season average. However, the books have put this line at over/under 6.5 with the juice on the over.

With Andrew Abbott on the other side with his 8% K-BB% and 1.41 WHIP, I think I'll just bet on Kirby through the game lines.

Picks: Mariners Moneyline -150


Anderson's MLB Picks and Predictions for Monday, July 20

Follow me in the Action Network App for additional bet notifications.

  • Pittsburgh Pirates Moneyline
  • Pirates vs Yankees, Over 8
  • Toronto Blue Jays Moneyline
  • Rays vs Blue Jays, Under 7.5
  • Dodgers vs Phillies, Under 8
  • Boston Red Sox Moneyline
  • San Diego Padres Moneyline
  • Padres vs Braves, Over 9
  •  Jacob Misiorowski Under 8.5 K's
  • New York Mets Moneyline
  • Jameson Taillon Over 2.5 ER
  • Jack Flaherty Over 2.5 ER
  • Giants vs Royals Over 10.5
  • Nationals vs Rockies Over 12.5
  • Seattle Mariners Moneyline
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Jon AndersonVerified Action Expert

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