"She's a winner to me. That's my baby sister, she didn't let anybody down," said brother Jack Perry, one of more than a dozen family members who cheered the leggy blond throughout the show.
"She's standing up for a lot of people and she deserves everything that she wants. I'm proud of her."
Talackova avoided media after the three-hour gala, slipping away from the downtown theatre to leave the spotlight to 26-year-old Sahar Biniaz, a fellow Vancouverite who claimed the title and advances to the international Miss Universe competition in December.
But Talackova did not leave empty-handed. She was one of four contestants named Miss Congeniality.
Her lawyer Gloria Allred said Talackova also triumphed in a broader fight for equality.
"She won an 'herstoric' civil rights victory and that I think is frankly more important than anything, any victory she would win, even representing Miss Canada," said Allred, who flew in from Los Angeles to support her client.
Talackova appeared confident and animated onstage, throwing flirtatious glances over her shoulder as she strutted in front of the judges in a silky red dress with a plunging back. Later, the 23-year-old showed off her feminine curves in a white bikini and a tight-fitting white evening gown.
At 6-1, Talackova towered over several other contenders and was often easy to spot in the crowd of 62 hopefuls, even though she was often placed towards the back.
Her appearance onstage often elicited loud hoots from supporters, but the cheers barely drowned out muted boos when she was awarded Miss Congeniality.
In the end, audience member Andrew Smith said the right contestant won: "A lady."
"I'm happy a lady won. Most definitely," Smith said immediately after the show. "If a fake lady won it wouldn't have been right."
"But hopefully the (issue) gets talked (about) a little more, that people take it more seriously because right now it's not looked at as something that's serious. It's a lady pageant and women are supposed to be in it."
Pageant judge Justin Ryan applauded Talackova's performance but their decision considered many factors.
"There were lots of interesting qualities to lots of the girls and we had to think: 'Who could win this contest but could also go on to win Miss Universe?'" said Ryan, a celebrity designer known for co-hosting HGTV's "Home Heist" with Colin McAllister.
"And we collectively agreed that Sahar had that extra X factor if you like, that little bit of je ne sais quoi and we're thrilled that she won."
Talackova was initially barred from competing because she was born male but pageant owner Donald Trump over-ruled the decision and allowed her to compete.
She was born Walter Talackova and underwent a sex change operation four years ago.
Her journey attracted extensive media coverage during the run-up to Saturday night's final, catching the attention of 22-year-old Laura Fox who cheered for Talackova along with two friends.
"This is a pretty big moment, for Canada and for Jenna so we thought we'd come and support (her)," said Fox.
Her friend Sarah Moteelall agreed.
"Gender needs to be put into question, why not on the beauty scene where it's so defined, right?" said the 23-year-old.
"Beauty is not gender-based and it shouldn't be. She went through a lot to get up there and she's the first one and it boggles my mind that people even question gender anymore."
Calgary's Adwoa Yamoah was named first runner-up, Ottawa's Majd Soudi was second runner-up, Katie Starke of Uxbridge, Ont., was third runner-up and Toronto's Kesiah Papasin was fourth runner-up.
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