The Shady Side Of Caitlyn Jenner

Caitlyn Jenner is masterful at staying in the public eye. She's everywhere at all times, shooting down engagement rumors (to a transgender woman 47 years her junior) and demonstrating the dangers of skin cancer to her Instagram followers. That's to say nothing of her much-publicized Diversity Lecture at the House of Commons or her appearance on the "appalling" and inadvisably titled reality show Genderquake.

Prior to transitioning in 2015, the former I Am Cait star was known as Bruce Jenner, the handsome Olympic gold medalist and "all-American hero" who won the 1976 Olympic decathlon. Jenner was once again hailed a hero after her Vanity Fair cover and ballyhooed acceptance speech at the ESPY Awards

In recent years, Jenner's fallen somewhat out of favor with the public, the LGBT community, and her own family. Claims in her 2017 memoir, The Secrets of My Life, reportedly poisoned her relationship with ex-wife Kris Jenner and her stepchildren (particularly Kim and Khloé Kardashian.) These days, Kris is allegedly "done" with Caitlyn, and Kim accused her of being a garden-variety liar — albeit in an Issa London dress — and "not a good person."

They may have a point. Between Caitlyn's public gaffes, legal woes, and increasingly strained relationship with the transgender community, loads of evidence suggest the shade runs deep with this one. Take a look at some of the iffier news nuggets, and then ask yourself: Shady... or perfect lady?

Yes, there's room for some ambiguity here.

Her flip-flopping views on Trump

Caitlyn Jenner's views on Donald Trump flip back and forth like a comb over in a windstorm. Though she voted for him, she claims she's no longer in "allegiance" with the president in the wake of his "half-baked" military ban on transgender people in 2017. He must "reverse his position immediately," she said in a statement. However, days after making those comments, Jenner was snapped by the paparazzi tooling around Malibu, Calif., in her 1960 Austin-Healey convertible wearing one of those "Make America Great Again" caps.

Jenner assured TMZ the cap wasn't intended as a political message and claimed it was a big misunderstanding. She was allegedly heading to the country club and needed a visor to keep her hair in check. After fumbling in the closet, she fished out the red cap. She didn't scan the front for political sloganeering. Instead, she threw it on her head and hit the streets. She reportedly didn't even notice the slogan until after she'd played a few rounds of golf. Jenner also claimed she'd left her purse at Starbucks that day and was in a tizzy trying to retrieve it — and that's apparently when the fiendish paparazzi took the incriminating snap! "I apologize to all of the trans community," she said. "I made a mistake. I will never do it again and I'm getting rid of the hat."

Hypocrite or harried golfer? You'll have to decide that for yourself.

​She allegedly badmouthed Kris Jenner

In her 2015 Vanity Fair cover story, Caitlyn Jenner discussed why her marriage to Kris Jenner ended after more than 20 years: "Twenty percent was gender and 80 percent was the way I was treated." That was merely a preamble for the shade to come. 

Caitlyn's family found claims in her 2017 memoir, The Secrets of My Life, so jarring that the ensuing drama basically fueled Season 14 of Keeping up with the KardashiansAs one episode revealed in excruciating detail, Kris had many questions after curling up with an advance copy of the tawdry tell-all: "Why does everything have to be that Kris is such a b***h and an a*****e?"

Her main point of contention: Caitlyn claimed Kris knew about her gender issues throughout their marriage. As Kris griped to Kim and Khloé Kardashian: "All through the book, [it reads] 'Kris knew.'" In the memoir (via Page Six), Caitlyn Jenner wrote "this will always be a subject of dispute between [Kris and I]. She insists that she was taken by surprise by my ultimate transition..." This apparently devastated Kris, who told her daughters: "I've done nothing but open up my home and my heart to a person who doesn't give a s**t." 

Bottom line? "None of it makes sense," Kris said. "Everything she says is all made up." Kris said she's never been so "angry and disappointed" with anybody in her life: "I'm done. Done! Done-zo!"

Put another way: She is done.

Kim Kardashian thinks she's 'shady'

In November 2017, Caitlyn Jenner revealed to Cambridge News that she and stepdaughter Kim Kardashian were effectively estranged: "Kim, I haven't talked to in a year," she said. (By January 2018, Kim had reportedly managed to say "hi" to her, so... that's an improvement, huh?) 

Following the publication of her memoir, Caitlyn claimed her children "don't want me in their lives. They bashed me pretty badly." But it could be argued that Caitlyn bashed them pretty badly, too — in between hard covers, no less. 

The way Kardashian sees it (via an episode of KUWTK): Caitlyn "just literally started three families with three different people and f****d everyone over." Like her mother, Kardashian had issues with the memoir. Key passages reportedly insinuated that her father, the late businessman and defense attorney Robert Kardashian, "knew O.J. Simpson was guilty, but joined the defense team to get back at his remarried ex." Kim read from a copy of the memoir on an episode of the show, calling the whole situation "so shady." Kim claimed Jenner promised her that the final draft of the book wouldn't involve her. "She lied to me, because that is about me if it's about our dad." Kim adds, "if you talk about my dad, I will cut you."

Khloe Kardashian felt 'betrayed' by Caitlyn

Rumors about Caitlyn Jenner's transition were cropping up in tabloids long before the official announcement in 2015, but as lurid reports analyzed Jenner's nail polish and Adam's apple, the retired athlete still refused to come out to family, according to Khloé Kardashian.

In fact, Kardashian claims her stepfather would say the rumors were all untrue. During her appearance on The Ellen DeGeneres Show that same year, Kardashian recalls family members asking, "'Bruce, like what's going on? We're hearing all these rumors...?" In retrospect, she claims it's clear Jenner "knew he was transitioning and wouldn't be honest with us."

In a subsequent 2016 interview with the Howard Stern show, Kardashian claims the family didn't know Jenner was transitioning until the subject came up at a Keeping up with the Kardashians meeting with E! Entertainment execs. "They mentioned that Bruce was having a TV show about transitioning or something," she recalled. 

Oddly, Kardashian claims Caitlyn would only discuss the issue on camera — and never in private. She thinks this provided a sense of emotional "security," adding, "Maybe he felt like we couldn't get as upset or whatever." Kardashian said she found the lying and deception incredibly frustrating, especially since "each sister had a different story because he couldn't keep up. Just lay it on the table, what are we doing?"

Her joke about a shooting is a shocker

In June 2017, a 66-year-old small business owner named James T. Hodgkinson grabbed his handgun and modified assault rifle and headed to a GOP baseball practice in Alexandria, Va. He fired 60 rounds into the field, critically wounding House Majority Whip Steve Scalise, who collapsed near second base. Two Capitol Police officers, a lobbyist, and a congressional staffer were also wounded in the attack. In the end, the only fatality was Hodgkinson, who was gunned down by police. A fanatical Bernie Sanders supporter, the Illinois-based man was evidently driven by his fury over President Trump's election.

Three days later, in a misguided attempt at timeliness, Caitlyn Jenner evoked the tragedy while speaking at a College Republican National Committee convention. "Fortunately, the guy was a really bad shot," she said. "Liberals can't even shoot straight." 

That off-the-cuff attempt at gallows humor demonstrated something of a tin ear on her part, or at least an extraordinarily poor sense of appropriateness. People were outraged, with Salon scribe Matthew Rozsa writing, "It really says something when Ted Nugent shows more basic decency after a national tragedy than you." Twitter erupted, with celebs such as Debra Messing calling the comment "disgusting" and "shameful." 

Despite the backlash, Jenner did not apologize for the overzealous zinger. 

Her 'man in a dress' comment offended many

Jenner's folksy sensibility hasn't always helped her public image. A few off-the-cuff remarks in her 2015 Time interview managed to seriously rankle some members of the LGBT community. 

Discussing transgender issues in America, Jenner suggested life is easier for a trans person who "authentically kind of looks and plays the role." She also suggested it's crucial that trans people "project a good image for [the transgender] community." Then, in many readers' eyes, she totally blew it with this: "If you look like a man in a dress, it makes people uncomfortable." 

The backlash was swift and furious, with Jenner once again tasting the wrath of a vengeful internet. The Twitter hordes descended in droves, airing their grievances all over social media. Detractors called Jenner "transphobic," while others accused her of "invalidat[ing] the gender identities of trans women." 

This time, Jenner wrote a lengthy public apology titled "Still So Much To Learn." The open letter included a passage stating: "I guess I've come to understand that maybe I have made some mistakes, and I need to make my real feelings more clear." As opposed to what kind of feelings, exactly?

Joking about Republican bathroom scandals = Shade

From the Department of "Sick Burns:" In July 2016, Caitlyn Jenner was asked to speak at a Republican National Convention event in Cleveland, Ohio. She earned groans and grim glances aplenty for a joke about flushing feminine products down the toilet, and that was hardly the bluest material tested out on the crisply conservative crowd.

Eventually, her speech touched upon North Carolina's controversial House Bill 2, which proposed forcing people to use public restrooms in accord with the gender on their birth certificates. At one point, Jenner tried out a few jokes at the Republican party's expense, riffing on their unerring knack for getting caught with their pants down in men's restrooms.

Jenner mentioned "three Republican state representatives" — Mississippi Rep. John Hinson, former Idaho Sen. Larry Craig, and Florida State Rep. Bob Allen — "who were all arrested for lewd behavior in a men's bathroom." Jenner jokingly proposed that "maybe what we should do is ban Republican representatives at a state level from being in bathrooms, if we're trying to protect people."

The most shocking thing about the dig? The butts of the joke did not express outrage publicly. Perhaps they realized complaining would only shed more light on an embarrassing subject.

Her relationship with the LGBT community? Complicated

Some balancing acts are simply never going to work. Jenner tries to court the LGBT community while cozying up to fervid Republicans, such as former presidential candidate Ted Cruz. It's proven difficult, if not impossible, for people to wrap their heads around a trans woman supporting Cruz, a politician prone to having unsettling things fall out of his mouth, including comments about homosexuality being a "choice." 

Trans activist Sarah McBride told The Wrap that Jenner supporting the Texas politician was "the last straw" for many, and activist Zoey Tur quipped, "Someone needs to tell Ms. Jenner she's transgender. There's great disappointment among people in the community." Whistleblower Chelsea Manning called Jenner "the grinch who stole the trans movement," and The View's Joy Behar even compared Jenner's support for Cruz to "Jews For Hitler."

In 2015, Jenner came face-to-face with an angry mob of protesters as she tried entering a charity event in Chicago. The crowd chanted: "You're an insult to trans people! You are an insult to women!" The event itself was called I Ain't Cait, a dig at Jenner's former reality show. 

​Did her 'reckless' driving claim a life?

In February 2015, Jenner was involved in a fatal four-vehicle accident in Malibu, Calif., reportedly rear-ending a Lexus driven by 69-year-old Kimberly Howe, pushing it into oncoming traffic. Howe's vehicle was struck head-on by a Hummer, and Howe died at the scene. Investigators found no evidence of wrongdoing, and no criminal charges were filed against Jenner. 

But the blame game continued when Hollywood agent Jessica Steindorff, also involved in the crash, criticized Jenner for receiving the Arthur Ashe Courage Award in July 2015. Steindorff wondered how anyone could "honor a person who is responsible for taking a life." Steindorff claimed Jenner "failed to do the right thing and take responsibility for her actions. That same year, Steindorff sued Jenner for $25,000, claiming she'd been driving "negligently, carelessly, recklessly." The case was settled out of court, and then Jenner counter-sued

That wasn't the only lawsuit Jenner filed, and it wasn't the only lawsuit filed against her. Although police reported that Jenner was not being chased by paparazzi at the time of the accident, Jenner filed a lawsuit against the alleged paps in 2016, claiming "the Stalker Defendants" were "driving too close." 

Meanwhile, Jenner allegedly settled a wrongful death lawsuit with Howe's stepchildren. Another lawsuit, filed by the family in the Hummer, carried on until January 2018, resulting in a massive $800,000 settlement. By March of that year, that family was still waiting for some of the money, according to The Blast, and reportedly questioning the delay.