A first-round draft pick, 28th overall, by the Chicago Blackhawks, his NHL career has not yet fired to life. He logged 28 games for the Hawks and then 96 for Florida over three seasons after being traded to the Panthers that sent, among others, Kris Versteeg back to the Windy City.
Olsen is certainly a broth of a lad, standing 6-foot-2 and tipping the Toledos at 223 lb.
"Sometimes,'' reasoned Flames' GM Brad Treliving, "you can get too much too soon. Maybe that happened to Dylan. He went through some challenges, in his life, in his game.
"He didn't play last year. Still a relatively young guy. Big guy. Thinks the game good.
"A little bit of a wild card. We'll see."
Stockton Heat coach Ryan Huska knows Olsen from the 2012 World Junior Championships in Buffalo. They were both part of Canada's silver-medal winning contingent.
"Everything I remember about him is positive,'' said Huska on Thursday. "At that time, Dylan was the only guy, if I remember correctly, that came to us from an NCAA program. So I found him to be a quieter guy early on. He kinda had to feel his way around, get himself in with the group of CHL (players).
"In regards to his game-play, he was very steady for us, used as a heavier, physical, stay-at-home guy who kept things simple.
"A real reliable guy for us."
There's no risk involved in the Flames in all of this, of course. Should Olsen show enough to warrant a contract, it'd be like finding a $100 bill on the pavement while walking the dog.
"Sometimes when you have a guy coming in this type of situation it's almost like a trade deadline deal,'' said Huska. "It's really a bonus if he stays. "Whether or not this affects our group in Stockton, that'll depend on how Dylan plays. But he's got an NHL resume. He was a high pick, well-thought of.
"We're pulling for him. From my dealings with Dylan in the past he's a good young man, a very hard-working guy and you always want to see players you've spent a little bit of time with have success.
"He is one of those guys."
No promises. No guarantees.
But the only thing Olsen knows is that he's got another shot.
"My agent's been in talks with teams all summer and he kept telling me the Flames were one that's always been interested.
"So we worked on it, worked on it and then two days ago he called me and said: 'We might have an opportunity here with Calgary. If they give you a call, you'd better be ready.'
"And sure enough, (Tuesday), that call came. Pretty surreal.
"Having this second chance is … incredible. It doesn't happen very often so I'm going to do all I can while I'm here."