MLB Picks 8/21 – Red Sox at Yankees

By Thomas Quaynor for Wannamakeabet.com

Long-time, bitter American League East rivals begin a four-game weekend set tonight at Yankee Stadium as the Boston Red Sox (68-59) visit the New York Yankees (69-57) on FOX. This is the third series meeting and seventh head-to-head matchup between the AL East combatants. Boston has dominated the season series going 5-1 against New York, including sweeping a three-game set at home in the last meeting. All six of the previous matchups were played during a 9-day span in June. 

Boston is coming off a 4-3 extra-inning loss to the Baltimore Orioles at home on Tuesday. Newly-acquired slugger Nathaniel Lowe hit a two-run homer in the ninth inning that tied the game at 3. The Red Sox loaded the bases with one out in the 10th inning before a double play ended the threat. They also had a runner on third in the 11th inning with one out but couldn’t get the runner home. Boston was 0-13 with runners in scoring position and left 13 on base. 

The Red Sox were swept in the mini two-game series by the Orioles. They’ve lost three in a row. Tonight’s contest in the Bronx marks the beginning of an 8-game road trip for Boston. They’ll travel to Baltimore for a four-game set after facing the Yankees. 

New York held on for a 6-4 extra-inning win at Tampa Bay last night picking up their fifth win in a row. They swept the mini two-game series at Tampa and completed a 5-0 road trip. Giancarlo Stanton’s pinch-hit, two-run homer in the tenth inning gave the Yankees a 5-3 lead. Austin Wells hit a solo homer later in the tenth providing New York its final run. It was Wells’ second homer of the night. Yankees center fielder Trent Grisham also homered twice. 

New York’s much-maligned bullpen blew a 3-0 lead in the eighth inning, Tampa Bay scored once in the eighth inning and twice in the ninth. The blown save opportunity ruined the chance for rookie Cam Schlittler to pick up his second win of the year. The 24-year-old, 6-foot-6 right-hander had a perfect game going through the seventh inning. He finished with 8 strikeouts and 2 walks over 6.2 innings.  

Tonight’s starting pitchers are Lucas Giolito (8-2, 3.63 ERA, 87 strikeouts in 19 starts) for Boston and Luis Gill (1-1, 5.14 ERA, 14 strikeouts in 3 starts) for New York.

GAME ODDS

Moneyline: Boston (+123),  New York (-150)

Run Line: Boston +1.5 (-176),  New York -1.5 (+140)

Run Total: over 8 (-117),  under 8 (-104)

GAME STORYLINES: BOSTON

The Boston Red Sox went from a franchise synonymous with losing to being revered as champions after winning the 2004 World Series crown and breaking an 86-year curse. They went on to win three more World Series titles over the next 15 seasons (2007, 2013, and 2018). Unfortunately, Boston’s championship aura has waned in recent years after posting three consecutive non-winning seasons heading into 2025.

Boston appeared to be barreling towards another subpar season in 2025 due to an internal conflict involving superstar Rafael Devers. Boston’s management wanted Devers to switch from designated hitter (DH) to first base after Tristan Casas suffered a season-ending injury on May 2. Devers reportedly refused to make the switch, and it became a big issue surrounding the team as the season went on.

The conflict between Rafael Devers and Red Sox management eventually reached its boiling point when Devers was traded to the San Francisco Giants on June 16. The decision to trade Devers was stunning when you consider the 28-year-old, three-time All-Star had been one of Boston’s best players for the last 6 seasons. The Red Sox also gave him a 10-year, $365 million contract extension just two years ago in 2023. Devers led Boston in batting average, homers and RBI before being traded.

The departure of Rafael Devers could end up being addition by subtraction considering Boston was struggling to get to the .500 mark with Devers. Boston was 37-36 with Devers through June 16, and are now 31-23 without him. The Red Sox are currently 5.5 games behind first-place Toronto in the American League East and occupy the second Wild Card slot (No. 5 seed) just ahead of Seattle. 

At the plate, Boston boasts a strong lineup led by the foursome of second-year, emerging outfielders Wilyer Abreu (.253, team-leading 22 HR, 69 RBI in 108 gms) and Ceddanne Rafaela (.252, 14 HR, 52 RBI, 18 steals, 25 doubles in 121 gms), along with veteran shortstop Trevor Story (.259, 19 HR, team-leading 79 RBI, 22 steals, 21 doubles in 123 gms) and power-hitting third baseman Alex Bregman (.298, 16 HR, 52 RBI, 23 doubles in 81 gms).

The 26-year-old Wilyer Abreu and 24-year-old Ceddanne Rafaela were two of the top rookies in MLB last season and have been even better in year two. Trevor Story is finally healthy in his fourth year with Boston. He played in a total of 79 games over the last two seasons, and participated in 94 games in 2022. Alex Bregman signed a three-year, $120 million free agent deal with Boston prior to the season, and he’s been tremendous when healthy. Bregman was selected as an All-Star this season for the third time in his career and first time since 2019.

Boston added veteran first baseman Nathaniel Lowe as a free agent three days ago (Aug. 18) after the Washington Nationals released him on Aug. 16. The 30-year-old slugger had 16 homers and 68 RBI in 119 games with Washington. Lowe has a shot to surpass his career-high of 27 homers which he set with Texas in 2022. Lowe’s acquisition may bookend the Rafael Devers saga because he’ll likely fulfill the void at first base that Devers reportedly refused to.

GAME STORYLINES: NEW YORK

After a rare down year for the mighty New York Yankees in 2023 — they finished 82-80 which was its worst mark since 1992, they added then-25-year-old superstar outfielder and free-agent-to-be Juan Soto via trade in December 2023 and bounced back in a major way last season. The Yankees finished 94-68 in 2024 and advanced to the World Series for the first time since 2009. The stellar play of 2024 American League MVP Aaron Judge and Soto were the catalysts for the Yankees tremendous 2024 season.

It was expected that Juan Soto would agree to a long-term deal to remain a Yankee, but he ended up shocking the world when he inked a 15-year, $765 million contract with the New York Mets last December. New York received more bad offseason news in March when it was announced that ace Gerrit Cole would undergo Tommy John surgery and miss the entire 2025 season.

Despite the huge setbacks of losing Juan Soto and Gerrit Cole prior to the season, New York added big-name free agents in star pitcher Max Fried, along with former MVPs Cody Bellinger (2019) and Paul Goldschmidt (2022). Fried’s 74 wins over the last 6 seasons with the Atlanta Braves ranks second in MLB to the Yankees ace Gerrit Cole. 

The Yankees seemed to be cruising towards another dominant season this year through the first two and a half months of the year as they stood at 42-25 on June 12, and held a 4.5 game lead on second-place Toronto in the American League East. But a 7-game losing streak that began at Boston on June 13 triggered a prolonged stretch of dismal play for New York that lasted for nearly two months. The Yankees are just now rebounding from this terrible stretch as they’ve won 5 in a row and 7 of the last 8.

Faulty pitching outside of Max Fried and Carlos Rodon, along with inconsistent hitting in what looked to be an impeccable lineup is what led to the Yankees tailspin in June and July. Gerrit Cole and Juan Soto no longer being on the team in 2025 became a glaring issue during the Yankees struggles as both players would have likely remedied the issues. 

The Yankees added a pair of solid hitters in Amed Rosario from Washington and Ryan McMahon from Colorado in July to bolster the lineup. The recent return of 27-year-old, second-year starting pitcher Luis Gil should give a boost to the Yankees pitching staff. Gil was excellent as a rookie last year posting a 15-7 record with a 3.50 ERA in 29 starts.

Despite the somewhat turbulent season as a team, the incomparable Aaron Judge is amassing another stellar season at the plate. The 33-year-old reigning American League MVP is batting .330 with 40 homers, 92 RBI, 87 walks and 25 doubles across 116 games. He leads MLB in batting average and ranks fourth in homers.Judge is the favorite to repeat as AL MVP at -210. If he does take home the MVP trophy, he’d be the first player to repeat as AL MVP since Miguel Cabrera did it with Detroit in 2012 and 2013. 

The trio of left fielder Cody Bellinger (.272, 24 HR, 75 RBI, 11 stolen bases, 20 steals in 116 gms), second baseman Jazz Chisolm Jr. (.236, 22 HR, 57 RBI, 21 steals in 94 gms) and center fielder Trent Grisham (.249, 22 HR, 48 RBI in 109 gms) are all producing excellent seasons alongside Aaron Judge for what is arguably the best offense in MLB. New York’s 204 homers leads MLB. The Yankees 655 runs scored and +111 run differential rank 2nd.

THE PICK: YANKEES (Moneyline)

Boston has dominated New York this season — going 5-1 against the Bronx Bombers — but all 6 games were played over a 9-day span in June. Over the last 10 days, the Yankees appear to have rid themselves of the two-month doldrums they were in by winning 5 in a row and 7 of the last 8. I think they take care of business tonight in their return home to Yankee Stadium. Take the Yankees on the Moneyline!