Calgary's Jim Henderson is heading to the World Series with the Brewers

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When the Milwaukee Brewers open the World Series against the Tampa Bay Rays on Friday, a Calgarian will be helping run their pitching staff.

Jim Henderson, who was born in Calgary and played on the very first Okotoks Dawgs team in 1996, is the Brewers' pitching coordinator. He was promoted to the role in January after working his way up Milwaukee's coaching ranks.

"He's a Dawg through and through," said Jeff Duda, the Dawgs Academy pitching coordinator and a friend of Henderson's for more than 15 years.

A pitching coordinator sets the overall plan for how a team develops its pitchers, Duda said. In the playoffs, Henderson is also part of the staff building game plans for every situation they can think of.

"If everything goes according to plan, great. If not, they got plan B, C, D, E, you name it," Duda said. "They have a plan for every conceivable outcome."

Duda credits Milwaukee's collaborative approach for its pitching success. The team finished the regular season with the best record in baseball at 103-59, and swept the Los Angeles Dodgers in the National League Championship Series.

"It's not just one guy's way or the highway," Duda said. "They just kind of tinker with everything."

Henderson's own path to the majors was anything but quick. After playing for the Dawgs, he went to college in the United States and was drafted by the Montreal Expos in the 26th round in 2003, out of Tennessee Wesleyan, an NAIA school.

He spent years in the minors with the Cubs and Brewers, won gold with Canada at the 2011 Pan American Games, and made his major league debut with Milwaukee in 2012 at age 29. In 2013, he was the Brewers' closer, with 28 saves and a 2.70 ERA. Shoulder trouble followed, and he later pitched for the New York Mets.

"It's the epitome of resilience, is what it is," Duda said. "He never gave up. Kept on grinding."

Henderson started coaching in Milwaukee's minor league system in 2018 and joined the major league staff as bullpen coach in 2022.

Henderson hasn't forgotten his roots. When he comes back to the area, he drops by the Dawgs facility in Okotoks to talk to the academy players.

"He's never too busy to take time and say what's up," Duda said. "Kids that he doesn't even know who they are in the program, they know who he is, and they'll go and ask him questions, and he takes the time to talk to them."

In March, Henderson helped set up an exhibition game between the Dawgs' top academy team and a group of Brewers minor leaguers, further expanding opportunities for the players.

Henderson was the first Dawgs alumnus to reach the major leagues. He isn't the last.

This summer, left-hander Matt "Tugboat" Wilkinson made his major league debut with the San Francisco Giants. Wilkinson joined the Dawgs Academy in Grade 11, was drafted by Cleveland in 2023 and was traded to the Giants in May in a deal for two-time Gold Glove catcher Patrick Bailey.

Three academy players also just committed to NCAA Division I schools, the Dawgs announced: Ethan Renaud of Okotoks to Wake Forest, Dallas Tanaka of Okotoks to Pepperdine, and Brooks Froese of Red Deer to Kansas State.

Duda, who has been with the academy since it started in Okotoks in 2009, said it has grown from two teams to eight, from 13U to 18U. Most players are from the Calgary area, and the academy is now turning kids away.

Game 1 is Friday, Oct. 23, in Milwaukee at 6 p.m. Calgary time. Game 2 is Saturday in Milwaukee, then the series moves to Tampa Bay for Games 3 to 5. You can watch the games on Sportsnet and Sportsnet+.