Legionaires coach hits milestone
U18 Legionaires coach becomes youngest coach in Elite Baseball history to hit 100 wins

Jamie May has spent his whole life surrounded by Legionaires baseball because of his father’s involvement and his own time as a player and coach. (Photo supplied)
By Chris Jones/The Oshawa Express
A Legionaires member has hit a personal milestone, as Jamie May is the youngest coach in the Ontario Elite Baseball League history to earn 100 wins.
The win came after a 10-0 victory over Team North 18U in Sudbury.
May, 25, played for Oshawa for several years before coaching them. He says the Legionaires have been a part of his life as long as he can remember.
He didn’t even know he was coming up on 100 wins until someone pointed out he was at 95.
“We started a little countdown,” he says. “We were in Sudbury for three [games], so I knew if we won all three of them then I would hit it. So, luckily we did and it was exciting.”
Heading into Sudbury, May says he was more focused on the team’s performance. They had dropped two in a row in Stouffville the weekend before, and were looking to get back on track.
Right now the team is heading into their elimination tournament to end the year.
“So really the only thing I was thinking about was just getting the team back to playing the right way after a tough weekend the week before,” he explains.
May says he hadn’t informed most of the team, having only told a couple of players before the game.
“The guys that did know, they were happy for me,” he says. “They came up to me right after the game and congratulated me – it was nice.”
This is the third year May has coached the 18U team. He says he’s comfortable with the group he has, and he’s happy with the decisions they’ve made over the years.
May has coached multiple levels with the Legionaires, earning records of 35-23 at 16U, 30-21-3 at 17U, and 35-12-3 at 18U. Along with his 100 wins, he has 56 losses.
However, May has also coached at the junior level, where he has a record of 0-0-1.
He says going back to get that first win at the junior level is something he wants to do. He also notes the team he coaches right now is heading to junior next year.
“It’s something that I’ve considered, coaching junior next year, depending on what happens with the current coach and what guys end up wanting to do,” says May. “I really like this age group and we have a good group of guys.”
May played for the Legionaires until he was 16 when he went to play for the Ontario Blue Jays for two years. He came back to finish his time as a player in Oshawa.
He says playing for the Legionaires is special for him in part because of his father, Troy, whose number is retired at Kinsmen Stadium.
Because of his father, May had always been around the game of baseball and the Legionaires.
“He used to coach all of the Oshawa teams, and he was really big into the Oshawa junior team – he used to coach them – and he won a ton of championships with them, and I was always at the field,” says May. “I’ve been pretty much living with baseball my whole life.”
The Elite 18U Legionaires now head into their elimination tournament. For more information or to view their schedule, visit baseballoshawa.com