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Bruce Jenner, one-time Olympic hero, is expected to discuss his transition to womanhood on Friday.

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There have been many milestones inside the House of Kardashian in the past several years, the residue spreading ever-wider from its reality-television mushroom cloud. There was the brassy wedding of the clan's chief ambassadress and a world-famous rap star, held in a Florentine fort built in the 16th century by the Medici family, and the Rubicon-crossing – not long after – of Kim's maiden Vogue cover. There was the collapse of the family's tent-pole marriage – that of puppet master Kris Jenner – and the rift caused by a wayward son (the one who recently compared his sister Kim with the character in Gone Girl). Privy, we've been, to births, breakups, makeups, innumerable magazine covers (120 and counting) and even President Barack Obama name-checking the gang in a speech during the White House Correspondents' Dinner.

Add to the archives: April 24, 2015. That's when we come to a fork in the arc that not even the late, great operatist Aaron Spelling could have foreseen: Long-time patriarchal figure Bruce Jenner is set, on Friday evening, to speak with ABC's Diane Sawyer in a two-hour interview expounding on, among other things, his transition into being a woman. A zeitgeist thunderclap, it's a media moment that serves to illuminate in umpteen other ways: as peephole into the life of an all-American hero (an athlete once as celebrated as, say, a Tiger Woods, at his peak), as an archetypal tipping point in gender politics, as Bruce's proclamation of emancipation from the women in his life (and the cirque de Kardashian) and, finally, as Rorschach test into the state of the TV one-on-one.

"My whole life has been getting ready for this," says the 65-year-old Jenner in one of the many promo clips that ABC has been teaspooning out in recent weeks. A life – for those familiar with the long horizon – that is just the saga we might get if a master like John Irving or Richard Ford sat down and collaborated with a Jackie Collins. It reached its earlier apogee, in 1976, right here on Canadian soil, when Jenner nabbed the decathlon gold medal at the Montreal Olympics, smashing a world record. Having battled dyslexia in school, and having put his focus into sports as a means of coping ("If I wasn't dyslexic, I probably wouldn't have won the Games," he once said), he successfully morphed into a poster boy. He was in Wheaties commercials. He appeared in films and television. He palled around with other biggies of the era – with Mikhail Baryshnikov, at Studio 54, with Muhammad Ali. There were Bruce Jenner dolls. He even played the part of inadvertent pawn in the Cold War, having bested a Soviet athlete at those seminal Olympics.

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And long before he'd be known as part of a conga line brought to us by the letter "K" – a Mike Brady of sorts to Kim, Khloe, Kourtney, Kendall and Kylie – his six-degrees-ism was stellar. This is the fella once married to Linda Thompson (who famously had a relationship with Elvis Presley, and following her marriage to Jenner, wed Canadian composer David Foster, whose own latest wife is Yoldana Foster, one of the Real Housewives of Beverly Hills). If the worlds of Kardashians and Housewives are porous in our present pop milieu, then it's only because both emerged from the first, too-real reality show, aka the O.J. Simpson trial – Kris Jenner's late husband, and mother to her first four children, was, lest we forget, Robert Kardashian, rising to prominence then as a member of O.J.'s defence team.

Fast-forward to 2015: the interview with Jenner. It's a "get," as they say in the news biz, but nearly retro in form. In a world where personalities themselves increasingly break news via Twitter, Instagram and YouTube (like Hillary Clinton's recent presidential announcement), the blockbuster TV sit-down is a piece of media orchestration in retreat. Indeed, the heyday for this sort of stop-the-presses pas de deux was the nineties: the Barbara Walters/Monica Lewinsky spectacle (still the highest-rated TV interview in history, with its 74 million viewers), Oprah's prime-time toe-to-toe with Michael Jackson, Martin Bashir's explosive exclusive with Princess Diana. It's the latter who casts a wee shadow here: In the same way that Lady Di – a master at using images, as Camille Paglia has said, "to send messages of allure, defiance or revenge" – used that pivotal interview, in 1995, to throw a media grenade at Buckingham Palace, Jenner has the opportunity, whether consciously or at some Freudian sea level, to steal back some of the spotlight from Kim & Co.

In the same way, too, that Diana's every downward-gaze and frozen smile was captured in a flicker of images while her marriage to Prince Charles was blowing up, we have here the truth by 1,000 paparazzi cuts, as a plethora of 1,000-words-worth photos have steadily shown Jenner's changing physical transformation over the past year, including the flattening of his Adam's apple. Like Diana, with whom there always existed a push-pull in terms of her relationship with the monarchy – in the end, she was inextricably linked to the royals as the mother of a future king – Jenner can never fully escape his brood either. The Faustian bargain is all too real – they're stuck with each other, in reality, and in TV.

The current spotlight on Jenner, meanwhile, comes 47 years after the first sex-change character in a novel (and later movie) – Gore Vidal's Myra Breckinridge. In 1999, Hilary Swank won an Oscar for a similar role in Boy's Don't Cry, just as the march for social acceptance continues today with Jeffrey Tambor's depiction of a transgender life in the critically acclaimed Amazon series, Transparent.

Adding to the particulars of Jenner's tele-tell-all this week is the woman who will be acting as a vessel for his story, registering her trademark concerned look throughout, no doubt. One of America's enduring blondes, Diane Sawyer's own transition is one for the books: from one-time press aide to Richard Nixon to moxie-carting star journalist to one of the more gilded of New York salon-keepers, after marrying Mike Nichols, the famed director of The Graduate and much more. The Jenner sit-down marks her biggest return to the public eye, after a) the death of Nichols, and b) leaving her post as chief anchor of ABC World News Tonight. In a career full of firsts, and highs, it may – amazingly enough – be an interview with Kim Kardashian's ex-stepdad that constitutes Sawyer's own comeback, too.

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