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.

Despite being part of the Kardashian-Jenner crew, Brody Jenner isn't necessarily a big fan of America's First Family. According to a source cited by Page Six in April 2016, some of Brody's "pals" were overheard at Coachella congratulating the reality star on his family's successes — meaning that of the Kardashian side. He apparently didn't take too kindly to the compliment and allegedly replied, "They're not my f**king family!"

Regardless of whether Brody actually publicly slated the Kardashians, it seemed the television personality was long annoyed that his would-be plus-one, then-new girlfriend Kaitlynn Carter, didn't get an invite to Kim Kardashian and Kanye West's wedding in Florence, Italy in May 2014. Brody allegedly voiced his dismay on the Kimye nuptials situation in a since-deleted Instagram post the following year: "Look...@kaitlynn_carter and I finally get to go to a wedding together!!!" Not one to let the apparent diss slide, Kardashian herself appeared to respond to Brody's comments during an episode of Keeping Up with the Kardashians. "I don't know why Brody is still talking about this," she said at the time (via In Touch). "We were very strict about our wedding ... Everyone else respected that — it's not a big deal. We love our stepbrothers. It just seems like they are always talking about this divide." 

Can't the KarJenners just get along?

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.

Brandon Jenner and ex-wife Leah Felder had been together for 14 years by the time they announced their breakup in September 2018, and were in a music duo together called Brandon and Leah. Just weeks after the former couple were officially divorced in mid-July 2019, this Jenner bro shared that new girlfriend Cayley Stoker [pictured, right] was three months pregnant ... with twins. You do the math. 

"We are at 12 weeks now, so near the end of the first trimester," he explained while revealing the happy baby announcement with People. "We're madly in love and we are very excited about this!" Brandon already shares young daughter Eva James with his ex-wife, and the trio apparently broke the news to her together. "Leah, Cayley, and I sat down with her and told her what was happening, and she was very excited and happy," Brandon continued. "She's super excited to be a big sister." How cute is that? 

While the timing of it all — mixed with Brandon's close relationship with his ex — might seem strange to some, it's clear that the former family unit has maintained nothing but respect for one another. "Leah and I split up in a really beautiful way," the reality TV star added. "And I think we handled it in the best way possible." And now everyone's moving on. We love a happy blended family!

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?

Just as Brody Jenner has allegedly dissed his family connections, older Jenner brother Brandon isn't a fan of his hugely familiar last name. In an interview with Channel Q Radio's Let's Go There with Shira & Ryan in June 2019, Brandon revealed, "When people hear it for the first time, or they hear my last name, 'Jenner,' I think that they're quicker to write me off and not necessarily even want to give my music a chance because of it" (via Us Weekly).

Basically, Brandon thinks that his super famous familial connections may have hindered his musical success. "I sometimes am almost a little ashamed of it, because I feel like people are going to have this preconceived notion that I'm just, kind of, like a spoiled kid that doesn't really have anything to say, right?" the musician continued. While Brody has apparently tried to distance himself from the Kardashians, Brandon also noted that the E! reality show's success has had an indelible impact on his life and career. "Things have changed for me a lot," he explained on the radio show. "Just the rise of Keeping Up with the Kardashians has changed the idea of what the last name Jenner, you know, what kind of person I'm going to be."

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!

During Brody Jenner's 2015 appearance on On Air with Ryan Seacrest, then-girlfriend Kaitlynn Carter participated in a phone-in and appeared to make some pretty major revelations about the reality star's love life. When the titular radio host asked whether it bothered her to hear about her then-boyfriend's previous escapades on his show, Sex with Brody, Carter replied, "I knew what I was getting myself into when we first started dating, so that was sort of something I had to accept from the beginning." 

Seacrest proceeded to jokingly call Jenner a "mutt," before asking Carter how many girls The Hills star had actually slept with. While Brody himself quipped that he'd "lost count past ten," Carter revealed, "It's more than a hundred." It's unclear whether or not this was a joke, but she followed up her estimate with, "I don't know, but I have an idea." For his part, Jenner was visibly embarrassed with his own girlfriend suggesting such a high number, but also said that they were very honest with one another. While there's nothing inherently wrong with Brody Jenner allegedly engaging in sexual activities with whatever number of people, the fact that he has no idea exactly how many is a little shady.

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.'"

Not all relationships last forever, but the tattoos some people get during said relationships do. And while covering up or removing a regrettable tat is sometimes an option, Brody Jenner is apparently pretty comfortable with keeping his. During his two-year romance with Avril Lavigne, the reality TV star ended up getting several matching tattoos with the Canadian songstress — including having her name etched into his forearm. Despite breaking up in 2012, Jenner's ink was photographed as recently as June 2019 ... meaning that this particular tattoo probably even outlasted his marriage to Kaitlynn Carter. For her part, Lavigne reportedly also got this Jenner brother's name tattooed on her body, according to The Daily Telegraph, while both celebs had matching lightning bolts inked on them. 

Brody Jenner is obviously pretty comfortable with the tattoos he got with his former flames, but the general public? Eh, a bit less so. As TMZ brutally reported in 2010, "Tattoos are permanent, boyfriends are not." Similarly, Cafe Mom threw shade at the pair following their split with, "The love may have worn off, but those tattoos sure haven't." Ouch. We suppose that's the price you pay for precious memories.

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?

Viewers of The Hills: New Beginnings will be well aware of the ups and downs that Brody Jenner and Kaitlynn Carter experienced throughout their time on the show. And it seems that Jenner is perfectly happy for his break up to be broadcast on television, too. Speaking to Entertainment Tonight in October 2019, Jenner revealed, "I'm sure you're going to see a lot of that," in reference to his separation from Carter. He then teased, "Of course, you have to stay tuned to see what goes on with that. But, you'll definitely see some of that," suggesting that he's focused on ensuring everyone watches the reboot of the reality show that made him famous.

Jenner also told Entertainment Tonight, "The Hills was one of those things where, it's tough to put yourself out there like that but ultimately, it can be very therapeutic as well." Whether or not it's really cathartic to watch your marriage fall apart on television is anyone's guess, but there are some who think Jenner's attitude towards his ex is even more callous than he's willing to reveal. To wit: A source told InTouch Weekly in November 2019, just a few months after their split, "[Brody] doesn't care about Kaitlynn anymore." It appears that the failed marriage is about to become reality TV fodder.