Making to the National Hockey League is really tough to do. Sometimes it happens when a player is a teenager. Sometimes it happens much later on.
To commemorate Nick DeSimone’s NHL debut on Monday night with the Flames, here are the 13 oldest players that made their NHL debuts with the Flames franchise (all after their 27th birthdays).

Sergei Makarov

The Calder Trophy winner in 1989-90 – the league changed the age requirement after that season – Makarov made his NHL debut on Oct. 5, 1989 at 31 years, 108 days. He was a 12th-round pick of the Flames in the 1983 NHL Draft and was effectively already a Hall of Fame-worthy player before he came over to North America due to his exploits with the Soviet national team.

Jiri Hrdina

An 8th-rounder in the 1984 NHL Draft, Hrdina was a product of Czechoslovakia and transitioned to North American hockey following the 1988 Calgary Olympics. His NHL debut on Mar. 3, 1988 came at the age of 30 years, 58 days.
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Pavel Torgaev

An 11th-rounder in the 1994 NHL Draft, Torgaev was a Russian product who came to North America fairy late. His NHL debut on Oct. 25, 1999 came at the age of 29 years, 273 days.

Mathias Johansson

A Swedish product, Johansson was selected by the Flames in the 3rd round of the 1992 NHL Draft. He didn’t make his NHL debut for a decade after that. He finally made his first NHL appearance on Oct. 12, 2002, at the age of 28 years, 232 days. (It was his lone North American campaign, as he soon returned to Sweden.)

Rick Mrozik

Selected by Dallas in the 1993 NHL Draft (in the 6th round), Mrozik played four years in college with the University of Minnesota-Duluth, then bounced around minor pro for a few seasons. He made his NHL debut on Apr. 4, 2003, at the age of 28 years, 92 days.
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Jakub Nakladal

Undrafted, Nakladal was a European free agent signing by the Flames out of the Czech Extraliga. He made his NHL debut on Feb. 9, 2016 at the age of 28 years, 41 days.

German Titov

Another Russian draft pick, Titov was selected by the Flames in the 10th round of the 1993 NHL Draft. He came over right away but was already fairly advanced in hockey age: his debut came in the season-opener on Oct. 5, 1993 at the age of 27 years, 354 days.

Nick DeSimone

After three years at college and several seasons in the AHL, DeSimone made his NHL debut on Nov. 7, 2022 at the age of 27 years, 351 days.

Jukka Hentunen

A 6th-round pick in 2000, this Finnish product came over after one more season in Europe. He made his NHL debut on Oct. 13, 2001 at the age of 27 years, 163 days.
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Roman Cervenka

Another free agent signing out of Europe, Cervenka made his debut early in the lockout-shortened 2012-13 season. He made his debut on Jan. 26, 2013 at the age of 27 years, 47 days.

Dwayne Roloson

This Ontario kid didn’t hit college until he was 20, then spent parts of three seasons in the AHL in the Flames organization. He finally made his NHL debut, aged 27 years and 32 days, on Nov. 13, 1996.

Serge Beaudoin

A bit of an outlier, Beaudoin was undrafted in the NHL but spent parts of six seasons in the World Hockey Association before joining Atlanta as a free agent. His NHL debut came on Dec. 14, 1979 at the age of 27 years, 14 days.

Jonas Bergqvist

A 6th-rounder in the 1988 NHL Draft, this Swedish product stayed in Europe until the Flames won the Stanley Cup. He made his NHL debut on Oct. 7, 1989, at the age of 27 years, 11 days. He split that season between the Flames and the IHL’s Salt Lake Golden Eagles before returning to Europe.
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