Nine-year old little leaguers batting against Holyoke Hospital in the early 2000s faced an impossible situation.

Hit the ball to second base, and it was vacuumed up by Isan Diaz, who debuted for the Miami Marlins in 2019 and played four seasons in the big leagues. Hit the ball to shortstop, and it was gloved by Jamie Westbrook, a recent call-up by the Red Sox who has played 19 games for the club in June and July.

“A ball that was hit to Isan or Jamie, that was definitely an out,” Holyoke Hospital coach Gabe Ofray recalled of life in the Holyoke Youth Baseball League. “It was a one-two like (Omar) Vizquel and Roberto Alomar, that’s how I see it.”

Westbrook played little league in Holyoke until he was 10, when his family moved to Arizona. After he was drafted by the Arizona Diamondbacks in 2013, Westbrook bounced around in the minors for 11 seasons before finally earning his first major league call-up this summer with Boston. Fenway is just a shade under 90 miles away from Westbrook’s old stomping grounds at Bonin Field, and dozens of his relatives have gotten the chance to see him play this summer.

“That’s where I was introduced to the game, and ultimately moved out to Arizona when I was 10, but my roots are definitely in Holyoke,” Westbrook said. “So I’m happy to be from there and hope to be representing the city well.”

Aside from Diaz, who played high school baseball at Central, Westbrook is the first Holyoke native to play in the major leagues since Mark Wohlers, a relief pitcher who won a World Series with the Atlanta Braves in 1995. Other Holyoke natives who played for the Red Sox include Joe Lucey (1925), Bob Adams (1925) and Tom Dowd (1901).

Westbrook also has a slew of relatives who played collegiate and professional sports, most notably Brian Westbrook, who played running back for eight years on the Philadelphia Eagles. Larry and Mike Westbrook are in the Holyoke Athletic Hall of Fame.

“Definitely, growing up with Westbrook, especially in Holyoke, you kind of have some lofty expectations of being a good athlete,” Westbrook said. “But I had unbelievable support and my family has been able to teach me which path to take and where they had faults in their careers to make sure I didn’t make the same mistakes, so I’m happy I’ve been given this opportunity and I want to make something of it.”

Westbrook played T-ball for Hamel’s Creative Catering, and in addition to Holyoke Hospital, he also played for the Mater Dolorosa Saints. 

“I remember the jamboree to start the season,” Westbrook said of the annual event at Springdale Park. “I remember MD Saints, we had our blue pants, I was all excited to wear them.”

He played at Bonin Field and Springdale Park and Mayer Field and Avery Field. He still remembers his frequent trips to Capri Pizza. And when his dad played softball games in the Flats, he grabbed food from the vendors, listened to the music and played with his friends and cousins for hours.

When Ofray first met him, Westbrook was eight years old and came running out of his parents’ car with his cleats already on. Ofray immediately noticed his “lightning quick bat.”

“It was always a sharp line drive, it was always a hard ground ball,” Ofray said. “Everything that came out of his bat, it was hard. If you want to call it Mike Stanton kind of batting, that was Jamie Westbrook.”

Led by the double play combo of Westbrook and Diaz, Holyoke Hospital went 35-1 from 2003 to 2006. Ofray recalled one championship game where Diaz bunted with the bases loaded and then Westbrook cleared them with a 250-foot home run to dead center field. After the first inning, it was 9-0.

If Diaz had two hits, Westbrook wanted four, Ofray said. If Diaz stole a base, Westbrook wanted three. When they weren’t playing together in little league, the duo often played pickle or wall ball at their fathers’ softball games.

“I think we definitely motivated ourselves to keep working and be as good as we could be,” Westbrook said.

As an elementary schooler at Mater Dolorosa, Westbrook was intent on improving his game, Ofray said. He asked how to improve his throwing and how to get more contact on the ball. He took extra ground balls after practice and cleaned them up afterward. Ofray compared Westbrook to a “tape recorder” with how quickly he incorporated his coaching points.

Though Westbrook spent his teenage years and the first decade of his professional career mostly on the west coast, he returned to the northeast in 2022 when he signed a minor league deal with the Yankees, his childhood favorite team. He hit 21 home runs in Triple-A for the Yankees last season, but never made the big league team, and signed a minor league deal with the Red Sox in free agency in December. Playing Triple-A ball in Worcester, he finally got the chance to visit back home regularly.

On off-days, he played golf with his grandfather at Shaker Farms in Westfield and grabbed Chinese food at Golden Peacock. He took a trip to Holyoke Sporting Goods and picked up a Holyoke hat and a hoodie.

“It’s cool to drive around the city and just reminisce, all the old places I used to play, seeing family and friends,” Westbrook said. “So it is a blessing to be this close and to have family at the stands at Fenway and Worcester.”

Westbrook got his first call-up by the Red Sox on June 2, and estimated that 30-40 relatives attended each of his first three games. 

“My uncles, cousins, you name it, they were all able to come,” Westbrook said. “So it’s nice to have some familiar faces in the stands rooting you on.”

He notched his first career major league hit on June 5 against the Braves and gave the ball to his mother, who’s now in remission from breast cancer. After 11 games with the Red Sox, Westbrook was sent back down to Triple-A, but he hit .341 with three homers and 14 RBIs across 12 games with Worcester to earn another call-up on July 9.

This past weekend, his Red Sox played host to the Yankees, and Westbrook had even more family from Holyoke come see him play in baseball’s biggest rivalry.