He was 15 years old for his first tryout, and the Hall of Fame second baseman knows the value of the opportunity to play in front of legions of scouts.
"I was playing baseball in Puerto Rico, like everybody does," Alomar said of his first tryout experience. "I was lucky enough that I had a father that plays baseball, so they knew that I loved the game. I went to a tryout, and all the scouts were there and I opened some eyes. And that's how you get discovered sometimes."
At Tournament 12, hundreds of kids will be in front of the eyes of many scouts over a five-day period between Sept. 20-24 for a series of tournament games and a skill showcase.
Unlike Alomar's tryouts however, this will give the participants a better opportunity to really highlight their skill level.
"For me, it was different than them now, because when I was there, we didn't have games. We just had practice. That was real tough to do," Alomar said. "Here you're going to have 10 teams, you're going to play against each other four times, so you're going to have more opportunity than just one day. That's the beauty of this. You can just go out there and play baseball."
The 10 teams will be representing provinces across Canada and will highlight Canadian amateur baseball players with college eligibility.
Ontario will have three teams, Quebec will have two, with British Columbia, Alberta, Atlantic Canada and a combined Manitoba and Saskatchewan team with one each.
Although there will be highly touted outfielder Gareth Morgan, among other standouts, at the tournament, it's some of the unknowns that Alomar is most looking forward to seeing.
"I'm looking forward for this opportunity for certain guys who may never have this opportunity," Alomar said. "There's going to be some of the guys that we know are going to be drafted, and some guys that may never have that opportunity in their lifetime. They're going to be here playing baseball, showing their skill. ... We just have to wait and see. We might find the next Brett Lawrie, Joey Votto or one of those guys.
"That's what it's all about -- to find that guy that not a lot of people are talking about."
Thirty years ago, when Alomar partook in his first tryout, he had the advantage of having a father who already played Major League Baseball, something that most, if not all, of these kids don't have.
But it wasn't his father's name that helped him catch the eyes of scouts, it was his own ability, and it acts as a reminder to stay within yourself and not try to do too much. Advice, he believes, will benefit everyone in the tournament.
"I approached it like it was just me," Alomar said. "I was there, just me. Just catching the ball, running the bases hard, swinging my bat, bunting, I did everything. I was prepared mentally. I was prepared to go out there and have a good practice.
"That's a message that I would give to the kids. Try to stay in your own game. Don't try to do too much."
Learning from his own experiences, Alomar has one final message for those participating in the tournament.
"Take advantage of the situation," Alomar said. "Come here prepared to play the game. Don't try to do too much. Mainly have fun, and on the other hand, try your best and don't waste this opportunity."