While I did include some guys that just grew up in Calgary in this ACGM, I gotta say, I'm pretty sure Calgary has the best starting lineup of guys actually from the city/in the correct position: Hall-Point-Nylander / Morrissey-Makar / L. Thompson. Toronto and Winnipeg are probably the closest, but Winnipeg is getting a little old and Toronto lacks the star forwards and a goalie still in North America. Some honourable mentions I found from cities I'm sure people will ask about:
Toronto (Hyman-Cizikas-Wilson / Pelech-Hamilton / Pasquale), shoutout R. Smith, Toffoli, C. Brown, Kyrou
Montreal (Duclair-Veleno-Chiasson / Matheson-Letang / throw Vlasic in net or something)
Stockholm (Landeskog-Zibanejad-Bratt / Kylington-Nemeth / Enroth)
Helsinki (Teravainen-Borgstrom-Vesalainen / Juolevi-Lundell / Lankinen)
Edmonton (DeBrusk-Ennis-Gallagher / Connauton-Spurgeon / S. Skinner)
Winnipeg (Domi-J. Toews-Ma. Stone / Keith-Mi. Stone / Reimer)
London (put Kadri on LW-Suzuki-Konecny / DeMelo-Doughty / J. Brown is big), shoutout Thornton, Carter, Horvat
Regina (put Sillinger on LW-Getzlaf-Eberle / Bear-Dumba / put H. Fleury in net)
Moscow (Ovechkin-Barbashev-Podkolzin / Zadorov-Zaitsev / Shesterkin)
Kitchener (Pearson-Scheifele-Hoffman / Hague-Stanley / Bastian in net I guess lol)
Saskatoon (Beckman-B. Schenn-put Stephenson on RW / McNabb-L. Schenn / Kuemper)
Markham probably had the best line in hockey in 18-19 (J. Skinner-Stamkos-Marner) but they don't have any D or G. Most American cities don't have more than 3 or 4 active players (like Buffalo has P. Kane and the Foligno brothers, Madison has R. Suter, Kessel, Schmaltz, and C. Smith, but they don't even have warm bodies for me to pretend to fill out a lineup lol).
Logan O’Connor, Matt Dumba, Jake Sanderson, Adin Hill, Taro Hirose, and Tyler Myers were not born in Calgary, but they were raised there (a lot of them went to the Edge). Half the sites say Twarynski is from Calgary, the other half say he’s from St. Albert so who knows. Mike Green just retired, but he’s from Calgary too. Jeff Glass hasn’t played yet this year, but he’s still listed on the San Diego Gulls roster, so I guess he’s their 3rd stringer or something. Ty Rattie and Ben Thomas are playing in Sweden, Cody Almond is playing in Switzerland, Andrew MacWilliam and Kristopher Foucault are playing in Germany, and Hunter Shinkaruk is playing in the KHL (not Russia though, he’s on Dinamo Riga lol).
I mean if the count the rest of the GTA it's Toronto by far, but if it's just "Toronto", then yes, Calgary probably has the edge.
Well obviously, if you claim a sixth of the population of the most hockey crazy country in the world I'd hope you'd have a pretty good starting lineup lol, and Toronto alone is still well over double Calgary's population.