The Shady Side Of The Jenner Brothers

With MTV's The Hills: New Beginnings hitting our screens in the summer of 2019, Brody Jenner found himself back in the public eye once again. Along with older brother Brandon Jenner, Brody has been a stalwart of reality TV for over a decade. From his stint opposite Lauren Conrad on the original version of the Los Angeles-based show to his high-profile relationships with stars like Avril Lavigne, Brody Jenner's name has regularly been in the headlines ... but not always for the right reasons. But it was this TV star's highly publicized breakup from Kaitlynn Carter — and his ex's subsequent dalliance with Miley Cyrus – that truly thrust him into the spotlight in August 2019. Similarly, Brandon Jenner has had his fair share of drama. Just weeks after his divorce from wife Leah Felder was finalized that July, he announced that he was already expecting twins with new girlfriend Cayley Stoker.

If Brody and Brandon's surname seems familiar to you, that's because they're Kendall and Kylie Jenner's half-brothers and share Caitlyn Jenner as a parent. Following guest appearances on Keeping Up with the Kardashians, it might have seemed as though the Jenner bros. were on good terms with the Kardashian side of the KarJenner clan. However, a slew of comments to the press would suggest otherwise. Let's take a look at the shady side of the Jenner brothers.

As previously mentioned, the news that Brody had separated from wife Kaitlynn Carter broke in August 2019 — just over a year after celebrating their destination wedding at the Nihi Sumba resort off the coast of Indonesia in June 2018. Around a week after their split announcement, Carter was famously photographed kissing Miley Cyrus on vacation, shortly after the singer's own separation from her husband of just eight months, Liam Hemsworth. 

With snapshots of the two women spreading online, Brody decided to joke about the unexpected turn of events on Instagram. "Don't let yesterday take up too much of today," he captioned a photo of himself by the sea. In reference to the gossip regarding Carter and Cyrus, his Hills: New Beginnings co-star Brandon Thomas Lee commented, "Let's round this scandal out and post a pic of us making out." Brody quipped in response, "Watch out! Pics of Liam and I holding hands on the beach coming soon." For her part, Cyrus seemed less than impressed by the comment, and shot back with, "Go take a nap in your truck and cool off #HotGirlSummer." Oof, seems like the "Slide Away" hitmaker wasn't here for any jokes at her expense, especially when Jenner brought Hemsworth into the mix.

Despite making headlines over their beautiful Indonesian wedding in June 2018, it turns out that Brody Jenner and Kaitlynn Carter were never officially married. Wait, what? According to a source cited by Page Six shortly after the former couple announced their split in early August 2019, "The union wasn't legal." Considering their rep released a statement about their decision to "amicably separate," it seemed these exes would be able to avoid any potentially messy divorce paperwork in the process.

Remember the fuss this Jenner brother previously made over his lack of a plus-one invite to Kim Kardashian's wedding? Well, The Hills star famously made it known that he was unhappy about most of the Kardashian-Jenners skipping out on his own nuptials. "My two little sisters, we never even heard from them. They never even RSVP'd I don't think," Brody told People. "We sent them an invite but we just never heard anything back ... I would have loved to have had them there." Meanwhile, Caitlyn Jenner also missed the wedding due to work commitments. But since it's transpired that the Jenner and Carter apparently never filed for a marriage certificate once back in the United States, meaning their marriage was never actually legal, perhaps that wasn't actually such a big deal?

Brody Jenner dropped a major bombshell regarding his relationships on The Hills while speaking with Yahoo! Lifestyle in 2015. Fans might have loved the supposed chemistry between himself and Lauren Conrad, but their entire romantic tryst was apparently fake. "I would say that the hardest part of it was having to live that fake reality," Jenner said. "And not being able to say, 'I didn't screw every girl on the show.'"

The reality TV star also found it difficult to push back against the ongoing rumors and misconceptions regarding who he'd actually dated in real life. "And then you get all these people saying, 'Oh, Brody's a male whore. He sleeps with all these girls,' when in actuality I didn't do that," Jenner continued, before opening up about his so-called fairytale connection with Conrad. "Lauren is a dear friend of mine and it was pretty funny having to live that reality," he said. "We would literally film a scene of us kissing or being in this lovey-dovey scene and right after it would be like, 'Cut!' And right after it'd be like, 'Hey, it's good to see you,' and then we'd go our separate ways." 

Wow, reality TV just breaks our hearts again and again!

Caitlyn Jenner's gender-transition journey was well-documented on TV shows Keeping Up with the Kardashians and I Am Cait, both of which show how the former Olympian's children reacted to her coming out as transgender. However, fans in the Twittersphere were less than happy when Brody Jenner misgendered Caitlyn while jokingly wondering whether her name was inspired by his then-wife's moniker on The Hills: New Beginnings in June 2019.

"My dad, he also became a woman — don't want to forget about that one," Brody began during the series premiere (via Cosmopolitan). He added, "I had been dating Kaitlynn Carter for four-and-a-half years, and my dad came out and said that he wanted to be called Caitlyn." Understandably, the Jenner brother's incorrect use of pronouns (Caitlyn's preferred pronouns are she/her) made the reality star seem a bit tone deaf. 

However, Brandon jumped to his younger brother's defense amid the ensuing backlash on Channel Q Radio's Let's Go There with Shira & Ryan. "Accidents happen and people slip up and you shouldn't shame them for it," he said (via Too Fab). "There's not an ill intention." Brandon also explained that errors should be teachable moments, admitting, "I do that even with my family — when my brothers and sisters slip up here and there — I do encourage them to use the pronoun that my dad would prefer." The musician went on to point out that Caitlyn has told her children, "You can still call me 'Dad.'"

By all accounts, Brody Jenner's split from Kaitlynn Carter appeared to be amicable. A statement released to Page Six announcing their break up said, "They love and respect one another, and know that this is the best decision for their relationship moving forward." However, everyone is aware of just how quickly Carter moved on with Miley Cyrus, with photos of the pair kissing surfacing shortly after the Jenner-Carter break up was announced. So when Jenner went public with his new girlfriend, Josie Canseco (above right), so soon after his ex's fling was revealed, was the reality star trying to send a message?

A source told In Touch Weekly in August 2019, "If you didn't know better, you'd think Brody and Josie were dating for some time now." The publication also noted that Canseco had left a flirty message on one of Jenner's Instagram posts on August 11, just nine days after the announcement of Brody's split from Carter. Could it be that Jenner wanted the world to know that he'd moved on too? 

Jenner and Canseco ended their romance in October 2019, with an insider telling E! News, "Brody basically broke it off with her because it was getting too serious and he didn't want the pressure of a new relationship." While the exact timeline appears to be a little fuzzy, it's certainly convenient that Jenner coupled up at almost the same time as Carter and Cyrus did. Coincidence?