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MLB · Fri, Aug 14 · 6:40 PM

Red Sox at Pirates

O/U 8 · RL Red Sox -1.5

GARY'S PICK
Pirates Moneyline
MLBvs Red Sox· +108

Pirates
Moneyline

+108 · CASHED · BOS 4 · PIT 8

Red Sox

The pick & result

Published pick
Pirates ML +108
Published odds
+108
Result
Won
Final score
4-8

Odds are the American price printed with this pick, not a current offer. Wins, losses and pushes remain on the public record; a missing grade is not a win.

The read

Friday night at PNC Park, two rookie arms under the lights and two clubs arriving off blowout wins. The river is quiet, the wind is light, and this feels like a game decided in the middle innings.

Bubba Chandler is the difference for me. His command has tightened, he has allowed five earned runs across his past three starts, and that 98.5 mph fastball can overpower a Boston lineup carrying a .705 OPS against right-handers. Pittsburgh also has its leverage bullpen fully rested after Thursday’s complete game.

Jake Bennett’s season numbers command respect, but his form is slipping: a 5.19 ERA with seven walks over his past three starts, while Boston continues to manage his workload. Pittsburgh can stack right-handed bats against him, and I trust the home side to manufacture enough traffic before getting into the softer part of Boston’s bullpen. At plus money, I’m backing Chandler and taking the Pirates to win outright.

The research

The dated measurements the app shows under this card — observations with their sample and source, not predictions.

STARTER FORM

  • Jake Bennett: 5.19 ERA over his last 3 starts

    5.19

    He is carrying a 5.19 ERA over his last 17.3 innings with a 1.38 WHIP (1.04 season) — the 3.17 season line is doing a lot of work for him right now.

PLATOON EDGE

  • Esmerlyn Valdez (bats R) gets a LHP from the 4th spot

    1.173

    Esmerlyn Valdez's vs. Left line (1.173 OPS, 56 AB) sits well above his .806 mark the other way (116 AB). Tonight's starter Jake Bennett throws LHP, the hand he hits best.

COOLING OFF

  • Esmerlyn Valdez: .531 OPS in Last 15 Days

    .531

    Esmerlyn Valdez has completely lost his zone discipline over the past two weeks, chasing balls out of his power zone for easy outs. A .531 OPS reflects a hitter totally out of rhythm. Stick with his prop unders until he stops expanding the strike zone.

  • Bryan Reynolds: .536 OPS in Last 15 Days

    .536

    Bryan Reynolds is stuck in a prolonged dry spell, managing just a .536 OPS over his last 15 days. He's missing his pitch when he gets it and making late-swing contact that settles easily into gloves. Backing his prop unders remains the smart angle against Boston.

HR THREAT

  • Wilyer Abreu

    +550

    Gary's Take Abreu is the hottest power bat on this field — six home runs in his last fifteen games and a slugging line that's carried Boston's lineup through this stretch. The matchup only sharpens it.

FIRST INNING

  • PIT have gone quiet in the 1st: runs in 1 of their last 10

    1/10

    Bennett's allowed a .073 average in the first, about as clean as pitching gets, and it pairs with a Pittsburgh lineup that's scored in the first just once in ten games — the safest half of tonight's number. Chandler's stingy on contact too, but his 4.09 ERA in that frame says his trouble comes in bunches. If this first inning cracks, it's more likely Boston doing it against him in the top half.

RUNNING GAME

  • Boston Red Sox like to run — Henry Davis (49% caught) is the wrong catcher to test

    49% CS

    Boston likes to manufacture pressure with steals, but Davis’s 49% caught-stealing rate makes that unusually dangerous. The Red Sox may need to create movement through contact rather than challenge his arm repeatedly.

  • Pittsburgh Pirates like to run — Adley Rutschman (36% caught) is the wrong catcher to test

    36% CS

    Pittsburgh wants to create offense with its legs, but Rutschman’s 36% caught-stealing rate makes that a dangerous plan. One aggressive attempt could erase the Pirates’ best scoring chance.

HEAD-TO-HEAD

  • Pirates are 2-1 vs Red Sox this season

    2-1

    Pittsburgh holds a 2-1 season edge over Boston, but a three-game sample offers zero real predictive power. Tonight comes down purely to fresh execution at PNC Park rather than past history.

TEAM RECORD

  • Red Sox 6-2 in Jake Bennett's last 8 starts

    6-2

    Boston's doing its job around him — the lineup shows up, the pen doesn't turn close games into losses. Pittsburgh gets that version of the Sox tonight. That trend travels fine on the road.

REGRESSION

  • Esmerlyn Valdez: .250 AVG vs .208 xBA

    .208

    Esmerlyn Valdez's .250 average comes against a .208 expected (xBA) on 209 plate appearances. His wOBA sits at .394 against a .349 expected (xwOBA). Statcast grades the quality of his contact rather than the results, and the expected marks sit below what he has actually posted.

CLOSER WATCH

  • Aroldis Chapman

    27 SV

    Aroldis Chapman owns this job outright with 27 saves, well clear of Erik Miller's 4 saves and 10 holds. Chapman is completely fresh after 0 appearances in the last 3 games, and Boston enters as a -122 favorite in Pittsburgh tonight, making this a classic live save spot. Chapman is a set-it-and-forget-it elite start for saves this week; leave Miller strictly for holds formats.

FANTASY PICKUPS

  • Jake Bennett

    3.06 xERA

    His 3.06 xERA actually sits under the 3.17 season ERA, so the process has run a touch better than the results, which is a small buy-low signal. WHIP is a respectable 1.04, but the 6.5 K/9 is the lowest of this group and it caps the ceiling. He's on the road to face PIT. Deep-league only. The peripherals say the ERA has room to come down, but without the strikeouts he's replacement-level outside deep formats.

All research from this day

About this analysis

Who made it
Gary AI, an AI sports-analysis product operated by Gary A.I. LLC. No human reviewer is claimed unless one is explicitly named.
Published data
Daily picks first stored August 14, 2026 at 1:35 PM ET.
Odds record
The pick receipt shows the price printed in the published ticket. The matchup market and line ladder provide separate market context. Stored sportsbook sources: fanduel, draftkings, betmgm, betrivers, caesars, fanatics.
Accountability
Read the editorial standards, source policy, and corrections process.

Props on this game

4
  • GARY'S PICK
    JAKE BENNETTK'S UNDER 4.5
    MLBBoston Red Sox· -132

    Jake Bennett
    K'S under 4.5

    -132 · LOST · ACTUAL 6

    Boston Red Sox

    Bennett has finished with four or fewer strikeouts in five of his past six starts, and his season rate of 55 strikeouts over 76 2/3 innings does not support this number. Pittsburgh has four hitters in tonight's lineup carrying recent whiff rates of 20% or lower, giving Bennett plenty of contact-oriented at-bats.

    Boston has also been careful with his workload, while his recent starts have generally ended around the middle of the sixth. I see four strikeouts as the likeliest landing spot.

  • GARY'S PICK
    BUBBA CHANDLERPITCHER OUTS OVER 15.5
    MLBPittsburgh Pirates· +117

    Bubba Chandler
    Pitcher Outs over 15.5

    +117 · LOST · ACTUAL 15

    Pittsburgh Pirates

    I’m buying Chandler’s improved efficiency at a plus-money price. He has recorded at least 16 outs in five of his past eight starts and just completed six scoreless innings on 85 pitches against the Mets. His command has stabilized, and his velocity gives him a direct path through a Boston lineup with a .705 OPS against right-handed pitching.

    PNC Park and the light wind should help keep damage contained. I only need Chandler to get one out in the sixth, which is a fair ask given his current form.

  • THE LONG SHOT
    WILYER ABREUHR OVER 0.5
    MLBBoston Red Sox· +550

    Wilyer Abreu
    HR over 0.5

    +550 · LOST · ACTUAL 0

    Boston Red Sox

    Abreu is the hottest power bat on this field — six home runs in his last fifteen games and a slugging line that's carried Boston's lineup through this stretch. The matchup only sharpens it.

    Bubba Chandler has been two different pitchers depending on which side of the plate you're standing on: he's held right-handers to a .600 OPS with just two homers allowed all year, but lefties have hit him for a .747 OPS and eight home runs. Abreu bats left, squares up velocity as well as anyone in this lineup, and he's carrying real recent hard contact into the box tonight.

    PNC's short right-field line only helps a pull-side lefty swinging this well. Plus-550 on a hitter this hot against a pitcher this exploitable from the left side is a number I want.

  • THE LONG SHOT
    JARREN DURANHR OVER 0.5
    MLBBoston Red Sox· +700

    Jarren Duran
    HR over 0.5

    +700 · LOST · ACTUAL 0

    Boston Red Sox

    The batting average has cooled for Duran over the last week, but the contact quality hasn't — he's still squaring up baseballs as well as anyone in this lineup and he's got three home runs over his last fifteen games to show for it. He walks into the same crack in Bubba Chandler that Abreu does: lefties have gone deep eight times against Chandler this season compared to just twice for right-handers, a split wide enough to build a bet around. Duran already brings pull-side thump, and PNC's tighter dimensions down the right-field line won't hurt him if he connects. Plus-700 for a hitter with this kind of recent power output against a pitcher this vulnerable to left-handed bats is worth taking.

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