In 2009, the then-17-year-old right-hander had a dominant performance in the Pan American Junior Championships in Venezuela. Taking the mound for the United States 18-and-Under squad, Taillon struck out 16 Cubans en route to a 6-1 victory in the gold medal game.
It was the kind of big-time performance on a big stage that probably had something to do with the Pirates selecting him second overall months later in the 2010 Draft.
Now 21 and established as one of baseball's best prospects -- MLB.com has him ranked 15th overall -- Taillon again will have a chance to shine on the international stage at the World Baseball Classic. When he climbs the hill in Phoenix, however, the red and white on his uniform will not be accompanied by blue.
That's because Taillon is pitching for Canada, not Team USA.
The Pirates' No. 2 prospect was born in Florida and attended high school in Texas. But he maintains dual citizenship because both of his parents, Christie and Michael, were born and raised in Canada.
Though the designation represents nothing more than a biographical oddity for many U.S.-born dual citizens, Taillon said he takes his Canadian background to heart. In fact, he considers it as much a part of his identity as his American heritage.
So despite his previous service with Team USA, when Team Canada came calling with a spot in their starting rotation at the World Baseball Classic, it was easy to say yes.
"When they approached me, I hadn't thought too much into the topic. They were getting a feel for what my ties are, what makes me Canadian, and they mulled it over and came forward and asked me. I jumped right on," Taillon said.
"I don't see myself as 100 percent American or Canadian, I truly see myself as both. So [playing against Team USA] is not that weird to me. My parents definitely stressed growing up that we were both and made sure we got both our passports when we were young so that down the line we could take part in opportunities like this."
To this day, Taillon's connections to the Great White North remain deep. His father lives and works in Calgary, a brother resides in Canada, as does a grandmother and grandfather. With family in Vancouver, Toronto and outside Montreal, his Canadian heritage spans the entire country.
While growing up, his parents made sure to bring him to Canada on a regular basis.
"Pretty much all my family is from Canada and lives there, so they made the strong effort to get us up there to see grandparents and cousins, spend time with them," Taillon said. "It was really just about every year."
He still gets there for at least a couple of weeks every year. Last October, he visited his dad in Calgary, then traveled to Toronto, which he called his favorite Canadian city.
Of the four Pool D nations that will play first-round games in Phoenix, the United States is considered a heavy favorite with Canada just edging Mexico as second choice. The potential for Taillon to dominate any one game, even against a very good lineup, is among the reasons why Canada could advance for the first time in this the third Classic.
In 2012, he spent most of his second season as a pro with Class A Advanced Bradenton, where he went 6-8 with a 3.82 ERA. He struck out 98 batters and walked 37 over 125 innings.
After a promotion to Double-A Altoona, Taillon showed he could rise to the challenge of advanced competition by going 3-0 with a 1.59 ERA. In a limited, 17-inning sample, he stuck out 18 batters and walked just one.
Of course, it doesn't hurt to have that experience from his stint with Team USA.
"If the opportunity comes to face guys I've never faced before and in the end they hit a little different, my strengths are my strengths. I'm just going to do what I'm really good at," he said. "I pitched against Cuba in Venezuela and fared quite well, pitched against Panama there, too. It definitely helps to have that experience."
Canada features a powerful offense, led by Brett Lawrie, Justin Morneau and Joey Votto. Joining Taillon in the rotation are fellow Pirates farmhand Chris Leroux, Major League veterans Shawn Hill and Scott Mathieson and Minor Leaguers Andrew Albers and Mark Hardy.
Taillon said he researched the Canadian roster and likes its potential.
"I think our chances are really good. I think we're a sleeper," he added. "Got some good arms, got the guys like Justin Morneau and Brett Lawrie and Joey Votto. With good pitching and timely hitting, you can always surprise people."
Taillon is the only one of the 28 players on the Team Canada roster who was born and raised in the United States. He knows he's playing for a proud country and probably will take a little bit of ribbing from teammates about his mixed background. Ultimately, however, he's confident in his Canadian credentials and said he should have no problem fitting in.
"I'm sure I'll get the question, 'How are you actually Canadian?' or whatever, but I've got plenty of background to back it up," he said, chuckling.
Once Pool D play commences -- Canada's first of three games is Friday at 2:30 p.m. ET against Italy -- Taillon will have the chance to pitch his way into the heart of a country that's always held a significant spot in his. There is, however, one mark of most Canadians that doesn't describe the 6-foot-6 righty.
"My dad was a big hockey player. He played goalie in college, but I never got too into it," Taillon said. "I've been to a couple Maple Leafs games and I liked them, as far as that aspect goes. "But honestly I never really got too into [hockey]."