Red Sox vs Yankees Free Pick, MLB Free Picks, MLB Predictions 9/30/25

BOSTON @ NY YANKEES (NYY -135, 7.5)

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Red Sox vs Yankees Free Pick, MLB Free Picks, MLB Predictions 9/30/25

RED SOX @ YANKEES 9/29/25

In their stellar first seasons as the Boston Red Sox and New York Yankees' top starters, Max Fried and Garrett Crochet lived up to the hype. It gets real tonight.

After being acquired in the offseason, Crochet (Red Sox) and Fried (Yankees) excelled as staff aces at the heart of baseball's most illustrious rivalry. The left-handers will be the main stars of Game 1 of the American League wild-card series, which begins tonight at Yankee Stadium.

The winner of the best-of-three series advances to the division series as the AL East's bitter rivals square off in the wild-card round for the first time. There was no complete wild-card round in 2021, the Red Sox's last postseason appearance. In 2022 and 2024, the Yankees avoided this round by winning the AL East and earning a bye.

Fried, who signed an eight-year, $218 million contract in December, finished the 94-win season with a 19-5 record and a 2.86 ERA. His 19 victories led the majors and helped the Yankees overcome the loss of injured right-hander Gerrit Cole.

As the Yankees made a late run for the division title and earned the first wild-card spot, Fried finished the season 6-0 with a 1.55 ERA in his final seven starts. After Fried was 3-3 with a 6.80 ERA over eight starts from July 1 to August 16, his strong finish was well-timed for the pennant chase. The Yankees starting pitchers finished with a 3.61 ERA, third among playoff teams and first among AL postseason qualifiers.

It was against Boston that Fried started his recent hot streak. On August 22, he pitched six scoreless innings and gave up four hits in Boston's 1-0 win at Yankee Stadium. Additionally, he was 1-1 against the Red Sox during the season, pitching 18⅓  innings with a 1.96 ERA.

Fried is used to postseason gloom. He was 5-6 with a 5.10 ERA in 20 games (12 starts) with Atlanta, which included a victory in Game 6 of the 2021 World Series as the Braves defeated the Houston Astros to win the title.

Fried must concentrate on taming Red Sox slugger Alex Bregman, who is 5-for-9 in their meetings overall and 4-for-6 off him this season. This season, he held leadoff hitter Jarren Duran hitless in six at-bats and Trevor Story to one hit in nine at-bats.

Fried was a target for the Red Sox last offseason, but their move to Plan B has so far received an A-plus.

Crochet was acquired by Boston on December 11 from the Chicago White Sox. Crochet led the majors with 255 strikeouts, the most by a Red Sox pitcher since Chris Sale, another powerful lefty acquired from the White Sox, struck out 308 in 2017. Crochet won 18 games (18-5, 2.59 ERA) in his first season in Boston.

Crochet also has some momentum as he cruises into the postseason. He allowed three runs on five hits in six innings while striking out 12 batters in his final four starts, which included a victory in Boston on September 14 against the Yankees. Crochet fanned 39 in four appearances against the Yankees this season and finished with eight games with 10 or more strikeouts.

Against MVP contender Aaron Judge, Crochet has performed admirably, limiting the slugger to two hits in 15 at-bats. In addition to striking out ten times, including in each of their first six meetings this season, Judge homered twice off Crochet.

The series' three games are all played in New York, which earned the right to remain home as the playoffs get underway by finishing the season with a better record than the Red Sox (94 wins to Boston's 89).

This season, the Yankees' batting average against left-handed starters was .255. Paul Goldschmidt will likely replace Ben Rice at first base, and speedster Jose Caballero or Amed Rosario, who is 5-for-8 against Crochet this season, could take Ryan McMahon's place at third base.

Boone stated that Carlos Rodon, a left-hander, would probably be the Yankees' next pitcher after Fried in Game 2. Cam Schlittler, a right-hander who attended Northeastern University and was raised in Massachusetts, could start for New York if the series needs a third game.

According to Cora, right-hander Lucas Giolito will miss the wild-card round because of an elbow injury. Instead of taking the ball Thursday as planned, Giolito was in Alabama visiting the orthopedic surgeon who operated on his right arm in 2024. In Game 2 on Wednesday, Boston will start Brayan Bello, who has a 5-4 record and a 2.35 ERA in 65 innings over 11 career starts against the Yankees.

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FREE PICK: GARRETT CROCHET OVER 17.5 OUTS

Crochet has pitched at least 6 innings in 25 of his 32 starts (78%) this season. That includes each of his last 8 starts of the regular season. That also includes four starts against the Yankees in which he went 6-plus innings each time. With his current form, his success against New York, and the fact that this is a playoff game, Crochet should be able to hit his season average of 19.2 outs.