Wednesday night's ESPY Awards will mark Caitlyn Jenner's public debut, but it’s far from the first time that the former Olympian has attended the sports awards show.
"You have to give a performance when you go out on the athletic field and you have to give a performance when you go out in front of that camera," Jenner said at her first ESPYs in 2002, when she walked the red carpet with then-wife Kris as her date. "It's all about entertainment, it's about the show."
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Jenner is not expected to walk the red carpet this year before receiving the Arthur Ashe Courage Award, all part of controlling her heavily-guarded public image. But she’s no stranger to scrutiny.
"You're going to be scrutinized, the media's tough," Jenner told ET at the awards show in 2008. "They're going to write either positive or very negative. In the middle, who cares? So you just have to be very careful with yourself and what you do."
"We've been watching Caitlyn since her debut and every interview that she has given has been in a very controlled environment," ET’s Liz Applegate weighed in. "She's never agreed to walk the red carpet and that was a very calculated and media-savvy move, because the red carpet is a very brutal place to be. This way she can control what the story is."
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The red carpets were once a family affair for the Olympic gold medalist, who brought a different member of the Kardashian/Jenner clan every year. Back in 2006, her date was the first member of the brood to surpass her in notoriety, stepdaughter Kim Kardashian.
"It's kind of shocking," Jenner said of Kim’s new-found fame at the time. "I worked my butt off for years and years and years and you get some recognition and you know, you see these kids today and they're out there. It's a whole different type of generation."
Kim’s sister Kourtney Kardashian weighed in on media scrutiny on their family when she was Jenner's date in 2008.
"It's a little frustrating at times when some of the stories aren't always true, but you kind of just have to not take yourself so seriously and just kind of laugh about it," Kourtney told ET.
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Scrutiny has continued to follow Jenner in the months since her transition. Critics even claim that giving her the Arthur Ashe Award, making her the third consecutive LGBT recipient, is a ratings ploy by ESPN to cash in on her popularity.
"We've spoken to executive producers, they deny that," Applegate said, adding that Jenner receiving the award is "a really big deal. It sets up the next chapter in her life."
Jenner can always look to her past to help deal with media scrutiny. As attention on her family members grew with the popularity of their reality shows and public personas, she could always be counted on for words of wisdom.
"Don't give 'em any ammunition, that's number one, don't give the media any ammunition because they're going to run with it whether it’s true or not," she told ET in 2008. "You just have to be very careful."
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However, it seems Jenner’s biggest concern of the night might be what to wear, as she’s reportedly tried on 20 dress and skirt combinations for the awards show. No matter what she picks, all eyes will be on her, but Keeping Up With the Kardashians executive producer Ryan Seacrest is sure that she will handle the night with grace.
"There's no way to predict how this is all going to unfold but I think Caitlyn’s done an amazing job," Seacrest said.
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