Braden Montgomery’s Walk-Off Home Run in Debut Lands Him in Rarified Air

The 24-year-old budding star for the first place White Sox is the latest prospect from the Garrett Crochet deal to make his mark in Chicago.

Braden Montgomery’s historic debut should give the White Sox confidence in a bright future. | Kyle Sheridan/MLB Photos via Getty Images

Less than two years later, the Garrett Crochet deal is looking like a smart one for the White Sox. In December 2024 they traded Crochet to the Red Sox for four prospects, outfielder Braden Montgomery, infielder Chase Meidroth, catcher Kyle Teel and pitcher Wikelman González. All are contributing to a first-place White Sox team.

After a runner-up Cy Young season last year, Crochet is on the IL with a severe lat strain and a 6.30 ERA.

The Crochet deal is reminiscent of how well the Nationals did in trading Juan Soto to the Padres—quantity and quality. (Washington obtained five players, including James Wood, CJ Abrams and MacKenzie Gore, who was flipped for five more prospects.)

Montgomery, a first-round pick by Boston in 2024, looks like a budding star, especially after his historic debut. He became the second youngest of only five players to hit a walkoff homer in his debut.

Walkoff HR in Debut, Ranked by Age

Player, Year of Debut	Age
Miguel Cabrera, 2003 Marlins	20 years, 63 days
Braden Montgomery, 2026 White Sox	24 years, 58 days
Josh Bard, 2002 Cleveland	24 years, 146 days
Carlos Pérez, 2015 Angels	24 years, 190 days
Billy Parker, 1971 Angels	29 years, 238 days

What’s so impressive about Montgomery is that he is a switch hitter with power whose bat angle works naturally to the opposite field from both sides. That’s a rare combination. He also has a different setup from each side of the plate. To find the closest comp to Montgomery, you must find two hitters—one right-handed and one left-handed.

Of the five debut walkoffs, the first and oddest was hit by Billy Parker.

“I was so nervous I could hardly stand at the plate,” said Parker after his 12th inning, 410-foot homer off Floyd Weaver beat Milwaukee, 3–2.

At the time Parker was listed as 24 years old, two years after Angels scout Kenny Myers signed him out of Los Angeles. Only later was it discovered that Parker was born in Hayneville, Ala., in 1942, which made him 29 at his debut. What was he doing in the seven years between attending one semester at Alabama State on a football scholarship and signing with the Angels? It seems he played a bit for the barnstorming Indianapolis Clowns, but not much else is known.

Parker played parts of three seasons with the Angels before three seasons in the Yankees’ minor league system and two in Mexico. In his later years he served Surprise, Ariz., as director of parks and recreation and was active in running youth and adult sports leagues. In 2002, a year before Parker’s passing, the city named the baseball field at Surprise Stadium Billy Parker Field.

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