From the Vault: Jim Henderson

When it comes to baseball, Jim Henderson has always had something brewing.

“I got started real early, like five years old right into tee ball,” recalled the pitching coordinator with Major League Baseball’s Milwaukee Brewers.

“My grandfather passed away when I was young, and passed on a softball and a bat to me, and it just kind of seemed like it was a sentimental sport for my mom’s side of the family, so that’s kind of how I got into it.”

By the time he was competing in Little League baseball with Calgary West, Henderson became a part of a special group of players and coaches that formed the bedrock of what would become Okotoks Dawgs Academy.

“Just a great group of guys who were, for Canada and Calgary, were actually pretty good at baseball. And their dads loved baseball, as well, so that’s how it all came together,” said Henderson.

“I don’t want to sound conceited, but we were pretty good as a group … we noticed we had something special with this core group of guys.”

Dawgs Academy founder and managing director John Ircandia, whose sons Matt and Vince took to the diamond with Henderson, was one of the baseball dads helping the boys take their game to the next level.

With the formation of the Dawgs program in Calgary, Henderson joined the best teenage ball players in the city in traveling around Canada and the United States while facing stiff competition.

“We got away from Calgary and went on road trips and we were doing well and playing in different places and those are probably the biggest memories for me. We were young, we kind of had a chip on our shoulder with this newly organized team and we knew we had to make a name for ourselves,” said Henderson, who was both a pitcher and a hitter back then.

Baseball also became a place of refuge for Henderson when he was 14 years old and his father, Neil, died of ALS (amyotrophic lateral sclerosis), also known as Lou Gehrig’s disease. Neil was just 51 years old when he passed away in 1996.

“He found playing baseball helped him forget his troubles,” said Jim’s mother, Marilyn Meek, in a 2013 MLB.com interview.

“Anything serious in his life, he could get on the mound and just concentrate on the game. Baseball was good for him, definitely. The Dawgs became like family — the coaches were like fathers and the teammates were like brothers to Jim.”

Added Meek: “Losing his father, I think, taught him about determination and perseverance and courage … it made him grow up and face life’s challenges, that’s for sure.”

Henderson agreed that the Dawgs provided a major comfort to him at a crucial stage of his life.

“Perfect timing, I guess, for a kid at that age, losing my dad. That team formed right after I lost him, or right around that time. It distracted me. It helped me kind of get out there and just take my mind off things when I was out on the field,” he said.

“It was road trips and having these dads around that I kind of looked up to and they were the authority figures and kind of the way my dad would be, so they definitely picked up where he left off. It was perfect timing for me to have these influences in my life and I owe a lot to them. That was a special time in my life to transition into this other field. I’ve got to grow up and be a man now and find myself and those men, those dads definitely helped me out.”

After high school, the 6-foot-5 righthander went to Midland College in Texas, followed by Tennessee Wesleyan College, where he drew attention from scouts.

Meanwhile, the Dawgs program continued to grow and in 2003, a Calgary Dawgs summer collegiate franchise joined the Western Major Baseball League (WMBL), predecessor to the Western Canadian Baseball League (WCBL).

As he prepared for the MLB Draft, Henderson suited up for the WMBL version of the Dawgs during their inaugural campaign, which came on the heels of the final season of the Triple-A Calgary Cannons at Foothills Stadium.

“There was quite a buzz around the city, around the team, to have some kind of high level baseball around Calgary. It was exciting for everybody. There was some good fan support for those first few games. They did a good job of getting it out there that we were taking over the stadium for that summer,” recalled Henderson.

“It was exciting to play at a stadium I went to and watched the Cannons play in my whole life and actually step on that mound and do that.”

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GOING PRO

The Montreal Expos came calling during the MLB Draft, selecting Henderson 777th overall in the 26th round.

“I think I knew no matter what that I was going to sign and move on with professional baseball. Even if I was taken in the last round, I was going to go I think. I was just looking for my name to get called so I could move on,” said Henderson, who was also excited to be selected by a Canadian franchise.

His journey through professional baseball took him from the rookie level Gulf Coast Expos in 2003 to the low-A Vermont Expos later that year, followed by the Single-A Savannah Sand Gnats in 2005 and 2006, where he served primarily as a starting pitcher.

As Henderson was navigating life in the minor leagues, the Dawgs were gaining traction in the WMBL. They won a championship title in 2004 and they opened Seaman Stadium in their new home of Okotoks in the summer of 2007.

Henderson joined the Chicago Cubs organization that year as a Rule 5 draft selection and pitched for two seasons at the Double-A and Triple-A levels.

After being released by the Cubs, he inked a minor-league contract in 2009 with the Brewers, the team that ultimately made the most of his talents.

Working as a full-time relief pitcher, Henderson continued to climb the ranks of the Brewers, going from the Single-A Wisconsin Timber Rattlers in 2009 to the Triple-A Nashville Sounds of the Pacific Coast League (PCL) in 2011 and 2012.

He finally got his shot in the big leagues when he made his MLB debut on July 26, 2012 during an 8-2 loss to the Washington Nationals. Henderson tossed a clean sixth inning that included no hits, walks or runs and one strikeout.

The Calgarian put in a solid first season in Milwaukee. In 36 games and 30-plus innings of mound work for the Brew Crew, Henderson went 1-3 with a 3.52 earned run average (ERA), three saves and 45 strikeouts.

In 2013, he took over the closer role from another Canadian, John Axford, who had also pitched in the WMBL as a member of the Melville Millionaires. During that season, Henderson collected 28 saves over 61 MLB appearances while going 5-5 with a 2.70 ERA and 75 Ks.

“It’s not easy, nothing in Major League Baseball is easy,” noted Henderson, who also represented Canada at the World Baseball Classic (WBC) in 2013.

“To have those experiences young, and the Dawgs were able to give that to me, that translates for sure over to the big league level. It took me a long time to get to the major leagues and you’ve got to face some adversity. You can tie this all together with the Dawgs and how we faced adversity.”

The 2014 campaign spoke to that adversity. Henderson started the year as the closer in Milwaukee, but after pitching in just 14 games, he required season-ending shoulder surgery.

He spent the 2015 season in the minors before signing a minor-league contract with the New York Mets in December. Henderson rose through the minors again in 2016 and made a return to the major leagues, getting into 44 games with the Mets. In his 35 innings, Henderson racked up 40 strikeouts and went 2-2 with a 4.37 ERA.

Henderson’s final MLB appearance on the bump took place on Oct. 2, 2016 against the Philadelphia Phillies.

A pair of minor-league deals with the Cubs and Brewers followed the next two years but Henderson was unable to get into game action. He pitched again for Canada at the WBC in 2017, before setting his sights on other paths in baseball.

COACHING CREW

Once again, Henderson found himself in a familiar place … the minor leagues.

The Brewers sent him to the Single-A Wisconsin Timber Rattlers of the Midwest League to serve as a pitching coach in 2019. One of the pitchers he worked with there, Aaron Ashby, has been a clutch reliever for the Brewers during their 2026 postseason march to the World Series. Ashby picked up two saves and a hold during Milwaukee’s sweep of the Los Angeles Dodgers in the National League Championship Series (NLCS).

Henderson retained the role of pitching coach in the Brewers system at the Triple-A level in 2020 and 2021, ultimately earning another trip to Milwaukee as the bullpen coach of the parent club in 2022.

“I thought I’d be good at it, honestly,” admitted Henderson of the bullpen coaching role during a 2022 interview with Alberta Dugout Stories: The Podcast.

“There was a little bit of confidence going into the job interviews and stuff with it. As a reliever, spending so much time in the bullpen, understanding what that unit kind of feels like and looks like out there as a group, I felt comfortable in that space.”

Added Henderson: “Games are won and lost a lot of times in the late innings with the relievers, and it’s a beast of a role because you have got guys out there grinding for nine innings and then you can come in and change the game within a couple of minutes, right? So, you have to be able to handle that and you have to be able to support each other throughout those times.”

Henderson has remained with the coaching staff of the Brewers ever since, picking up different job titles along the way, including assistant pitching coach, strategy coach and major league pitching coordinator, the role he currently holds.

“There’s so many things that you can pull out of coaching that just makes you feel good, day-to-day, when your guys do well and you can teach them about the game or about life, whatever it is. Yeah, it’s special,” said Henderson.

The Brewers have now made four-straight postseason appearances, including a pair of Wild Card series losses and an NLCS defeat at the hands of the Dodgers in 2025.

With a World Series appearance booked – the first for the Brewers since 1982 – Henderson is hoping to capture baseball’s ultimate prize in the form of an MLB championship.

“We’re just trying to put guys in the best opportunity to win. We can’t go out and buy a bunch of horses, so we have to do things a little bit differently and this is how we do it. The players are bought in, they’re excited about it. Everybody gets an opportunity to be in good situations. That’s just Brewer baseball and the way we want to get ahead,” said Henderson in a 2025 MLB Network interview.

As he helps the franchise chase its first Commissioner’s Trophy, Henderson has never forgotten his roots.

He’s returned to Okotoks on several occasions to help coach and talk with players in both the academy and with the summer collegiate squad.

As the first member of the Dawgs to graduate to the MLB ranks, Henderson was inducted into the Okotoks Dawgs Hall of Fame in 2015. He was also recognized at Kore 4 (+14) Corner in Seaman Stadium as one of the original members of the Dawgs youth team.

“I couldn’t be here without them, obviously,” Henderson said of the Dawgs, who have now won eight WCBL championships.

“It’s hard to even say how important it was. It was beyond important for my development. It’s as simple as that.”

(This article is part of the Western Canadian Baseball League’s “From the Vault” series, which focuses on WCBL alumni and is sponsored by Sentinel Storage)