The Ghost of Diddy's Past Haunts Usher Into Endorsing Kamala Harris: A Theory

A month ago, Usher told Joy Behar that "voting is an individual choice." Now just 17 days before the election, Usher joined Lizzo at a Harris rally and told his fans to vote blue. What changed?

I remember how underwhelmed the world was when Usher was announced as the the Super Bowl LVIII halftime show performer. After Rihanna swooned America with an Emmy-nominated performance, packed with hits AND an unplanned pregnancy reveal, I wondered why Jay Z chose Usher to succeed Queen Riri. Usher had just completed a two-year-Vegas residency, but for some reason, Mr. Carter was not going to let Park MGM Las Vegas be the place the R&B singer’s career went to die.

Now looking back at everything that’s transpired since February, was it ever really about choosing the most talented halftime performer? Or has America been witnessing a meticulously orchestrated plan building goodwill around Usher before the shocking Diddy scandal was about to break, a story his name has been heavily attached to.

Between the federal raid leading up to Diddy’s arrest, the unsettling photos and videos resurfacing linking Usher as one of his main protégés, and now seeing Usher on stage yelling, “I LOVE KAMALA HARRIS!” to a room full of Democrats holding up periwinkle Harris/Walz posters at an Atlanta rally, 17 days before the election—Jay Z’s selection feels anything but random.

Weeks before Usher entered the political space, author Shane Cashman and I discussed the possibility of Usher being used as a political pawn in a bigger game.

“It’s almost like the people who are pulling the strings behind the scenes are like let’s show the American public and the world Usher again,” Cashman said on an episode of Inverted World Live.

These are my confessions:

After watching Usher’s Super Bowl performance, I, like most of the world, fell back under Usher’s spell. He gave it his all- singing and dancing his heart out to some of my favorite forgotten 2000s party tunes. With each spin, I could taste the rim of my red solo cup, downing a shot of Canadian whiskey I’d stolen from my parents’ poorly stocked liquor cabinet, feeling as dizzy as I did back then. At 45 years-old, Usher proved to the 123.4 million viewers watching- he still got it bad.

The general consensus in YouTube comments agreed: Usher deserved our renewed respect.

After that night, Usher has remained relevant in the news, but for all the wrong reasons: making headlines for his close connection to Sean “Diddy” Combs and his role in discovering Justin Bieber. His 2016 Howard Stern interview has been viral for months, a disturbing clip where Usher talks about the time he was sent to “Diddy Flavor Camp” as a 13-year-old boy, a camp he admits he’d never send his own child to.

Yesterday, Usher made front page headlines again, after joining Lizzo on stage at a rally in Atalanta to endorse Vice President Harris, an endorsement that’s being criticized as wildly tone deaf given his ties to Diddy during an ongoing federal investigation.

During his speech, someone shouted out, “I love you, Usher,” to which he replied, “I love you but I love Kamala Harris even more!”

“I want her to be the next president of the United States,” Usher declared before breaking into a sing along, asking the audience to sing Archie Eversole’s “We Ready” with him.

As I was playing this clip from the other room, my boyfriend yelled, “what are you watching? A humiliation ritual?” An observation I can’t blame him for. It felt like the ghost of Diddy’s past was holding an invisible gun to his head forcing him to appear enthusiastic for the bright future Harris and Walz are promising.

On September 19, The View host Joy Behar desperately tried pressuring Usher into endorsing Kamala Harris on air, praising the self-proclaimed mother of cat ladies, Taylor Swift, for her endorsement following the presidential debate. Usher responded by telling her he believes “voting is an individual choice” and that he doesn’t “get too deep into politics.”

During this episode, Usher admits that he will be voting for Harris but made it clear to Behar and the panel of liberal show hosts that he wasn’t going to be another celebrity who blindly tells his fans how to vote.

Usher received a lot of praise from YouTubers and various online media outlets for “standing on business,” and not caving into the “Wicked Witches of The View,” as YouTuber TheRealGospelChops hilariously put it.

So what changed in one month’s time?

While this may have been a small win for Harris, it was a big loss for Usher. The public is now scrutinizing him even more, suspecting his involvement with Diddy to be bigger than they imagined.

Top comments from the Atlanta rally YouTube video read:

• Diddy really walk out on stage with everything currently going on? Who organized this yanking yikes moment?

• He’s been made to do this. Campaign for Kamala and all your Diddy problems will go away

• Usher’s there so Kamala won’t release any of his Diddy tapes

• And so Diddy tape blackmail begins!

---

Usher’s “Peach” Skims Ad

While the world was busy questioning Jay Z’s decision choosing Usher to perform at the Superbowl, Kris Jenner and the Kardashian clan were busy capitalizing on it. They rolled out a Skims ad featuring a shirtless Usher, holding a peach wearing nothing but midnight blue Skims boxer briefs. The ad hit Instagram feeds on February 5th, just six days before the scheduled performance. Everyone called Kim a “genius” for the impeccable timing of the campaign.

Coincidentally, I was at the Los Angeles Apparel factory the same day the campaign launched with a Yeezy shoe designer friend of mine, looking at fabrics for a potential merchandise launch for Yeezy. While we were waiting in the factory, we bumped into the head of Skims marketing and started chatting briefly.

I complimented the Skims x Usher collaboration and asked her what the significance was behind the peach.

“What was up with the peach?” I asked, assuming it was an ode to Atlanta, Usher’s home base for 30+ years.

“I don’t know actually,” she replied honestly.

“Usher brought the peach the day of the shoot. That was a personal choice he made” she said.

In an interview with Zane Lowe, Usher revealed that the peach was an ode to Antonio “L.A.” Reid, the producer who signed Usher at 14-years-old and launched his career. L.A. Reid is a name that continues popping up during the Diddy Files, credited as the producer who appointed Jay Z president of Def Jam, the producer who helped Diddy launch Bad Boy Records and and the producer Usher allegedly “gifted Justin Bieber to” and gave him his big break.

“Even when you see the artwork, you will understand it,” Usher said. “When you see the peach, you get it. You understand where I’m from and what we’re doing.”

But with Usher’s name being attached to a lot of questionable Diddy stories- I don't think any of us really understand where he’s “really from” or what he was “really doing?” Is he a villain, victim, or both?

---

---

How Diddy, Usher and Bieber First Met

In 2016, L.A. Reid released a tell-all memoir “Sing to Me: My Story of Making Music, Finding Magic, and Searching for Who’s Next,” an autobiography that has been made it easy for internet sleuths to connect the dots between Diddy, Usher and Bieber.

“I live for opening doors for the young generation of creators…the deepest and most sincere feeling I get is when I meet an artist and they have that steel in their eyes and that fire and  passion,” Reid wrote in the memoir.

The music executive, responsible for launching the careers of many 90s and 2000s stars such as Usher, Pink and Mariah Carey, speaks proudly about his role in shaping these three men, which in hindsight seems like a misstep, oversharing details that raise red flags in 2024. Describing a 14-year old Justin Bieber as a “gift” and “beautiful 14-year-old boy” certainly isn’t doing him any favors right now.

Reid describes the time Usher brought Bieber over as a ‘gift’ to him, calling the young pop star a ‘beautiful 14-year old boy,’ before signing him to Island Records.

Just a year after being signed to Island Records, Bieber spent 48-hours unsupervised with Diddy at his mansion where the two went ‘full buck crazy.” Even though Scooter Braun originally discovered Bieber, Reid credits himself for giving the Canadian singer his big break.

L.A. Reid also speaks openly about appointing Diddy as Usher’s mentor for a year before sending him off to live at “Diddy Flavor Camp.” Reid thought that Usher needed to be “toughened up” and didn’t want him turning out “soft and pretty” so he turned him over to the “wildest party guy in the country- Puff Daddy,” admitting that this might not have been “responsible” but got the job done.

Reid helped Jay Z secure his place at the top of the hip-hop food chain, appointing him as president of Def Jam Records in 2004 (per Mariah Carey’s recommendation). He also is responsible for Diddy’s rise to the top, providing him with the tools he needed to start Bad Boy Records, even admitting to introducing Diddy to Clive Davis, who Death Row Records CEO Suge Knight accused of being Diddy’s “secret gay lover,” a rumor he heard from Interscope Records’, Jimmy Iovine.

“We in the office, in the Westwood Interscope office. I walked in Jimmy’s office. I didn’t have to knock on the door […] we was havin’ a conversation and he overheard somebody say something he probably shouldn’t have heard.”

“He said, ‘I’m here because Clive Davis told me that him and Puffy’s real tight. And, uh, you know, lovers.’ So I thought he was talkin’ like, they got love for each other. I’m like, aight. He said, ‘Nah, they are lovers.'”

“And I’m like, ‘Why do you keep saying that?' “I said, ‘Are they lovers, like, fuckin’ and suckin’?’ And he said, ‘I don’t wanna say that,’ but that’s what that means, right?”

-Suge Knight, via March 26th episode of “Collect Call with Suge Knight

L.A. Reid’s Sexual Assault Allegations

It’s not shocking that Usher would hold a peach to honor of the man who discovered him, but it is suspect that he’d confess to that given that Reid was also hit with a sexual assault lawsuit in early November 2023, filed in Manhattan weeks before Cassie Ventura filed her lawsuit against Diddy.

In a lawsuit filed by Drew Dixon, former Vice President of A&R of Arista Records, Reid’s former record label, Dixon describes situations seemingly parallel to stories detailed by Diddy’s accusers, accusing the music executive of abusing his power and then sabotaging her career after rejecting his predatory sexual advances.

Dixon accuses Reid of sexually assaulting her two times in 2001. The first incident documented in the lawsuit describes a time she was scheduled to fly on a private plane with Reid and other senior executives. Dixon claims when she arrived, Reid was the only person on board, and while waiting for others to arrive, he allegedly started fondling her without her consent “playing with her hair, kissing her and digitally penetrating her vulva without her consent.”

The second assault reported in the lawsuit took place in Reid’s car. Allegedly, Reid offered Dixon a ride from a work event, and while in the backseat, “Reid without Ms. Dixon’s permission or consent began to grope and kiss Ms. Dixon, who squirmed and pushed him away as Mr. Reid’s driver stared straight ahead,” before “again digitally penetrating Ms. Dixon’s vulva without her consent.”

Dixon claims her career suffered after she rejected Reid both times, so she left the label in 2002 and went on to study at Harvard Business School. Dixon blames Reid for cutting her music industry career short.

The Dixon lawsuit didn’t get nearly as much press as Diddy’s, but also includes a 1995 rape allegation against Def Jam founder Russel Simmons (also Diddy’s “Vote or Die” campaign partner), a claim he’s denied. Simmons has been living off the grid in Bali for some time now, leaving the country after a number of women came forward accusing him of sexual misconduct. Simmons denies that this is the reason he left the states and claims he has no reason to feel “unsafe in America.”

During our last Diddy deep dive, L.A. Reid was mentioned by our guest RedPillAlice, who blamed Reid for the rise and fall of R&B singer Blu Cantrell, in coordination with Jay Z, who he appointed president of Def Jam Records in 2004, the year he allegedly “forgot to renew” Cantrell’s contract.

As the Diddy case unravels, we’re hearing many stories of singers whose careers got cut short due to the gatekeepers in power at the time.

Reid and Usher Launch “mega” in 2024

Just two days before the Superbowl, on February 9th 2024, Usher released his first solo independent album, “Coming Home,” under a new music label he co-founded with L.A. Reid and Larry Jackson called “mega.” Forbes sang their praises with a headline that read, “Usher Steps Into (And Redefines) His Legacy Era,” speaking about this new venture with Reid and how Usher would be the first independent artist headlining the Super Bowl Halftime Show.

Usher is the first artist signed by the label.

“His system is what created that expectation for me, as a young artist,” Usher told GQ. “So now, damn near 25 or some odd years later, we feel inspired to go out and create more artists.”

Usher and Reid allegedly had a falling out after Confessions came out, but reconnected in 2021 and have been working closely together since. The mega Instagram account is currently active, with Usher’s photos taking up the majority of the grid.

---

Jay Z’s Partnership with the NFL

Just yesterday, the NFL announced they will be extending their partnership with Jay Z’s Roc Nation, the program that’s been giving Jay Z free rein to pick halftime performers since 2019.

This partnership is part of the NFL’s Inspire Change initiative set out to focus on the league’s social justice efforts and started after the NFL received backlash for their treatment of Colin Kaepernick, who kneeled during the national anthem to protest police brutality during the 2016 season.

It’s been no secret that Jay Z has been in the driver’s seat selecting which halftime performers will hypnotize the audience of the most watched television program in America, last year’s viewership hitting an all time high.

According to sources, New England Patriots owner Robert Kraft reached out to Jay Z asking him to help the NFL with “social issues” and put him in touch with NFL Commissioner Roger Goodell, which eventually led to this $25 million a year partnership with Roc Nation and the NFL.

That same year in 2019, Kraft teamed up with billionaire Michael Rubin, and made Jay Z and Meek Mill, the face of a criminal justice reform organization REFORM Alliance. The organization started after Rubin set up a meeting between Kraft and Meek Mill.

Usher Performed at Michael Rubin’s 2023 White Party

Not many know that Rubin is a co-chair of the Prison REFORM Alliance. Most know him for being the white billionaire who popped up out of nowhere and took over Diddy’s White Party tradition, throwing lavish parties for the elite at his Hamptons mansion.

In 2023, Usher was chosen to perform at Rubin’s All White Party, months before he took the stage at Superbowl LVIII. Jay Z and Beyonce were among some of the celebrity guests in attendance, along with Kim Kardashian, Justin Bieber, J-Lo and other A-listers who were regulars of Diddy’s All White Party.

Diddy, however, was nowhere in sight.

And from the looks of it, he may have not been cordially invited. Were these billionaires and A-list celebrities in attendance intentionally distancing themselves from Diddy that summer, aware of what was coming?

---

Was Diddy Also Forced to Endorse Biden in 2020?

In our Diddy Files Political Deep Dive , we broke down all the times that Diddy endorsed political candidates. Throughout his career, he was a vocal talking supporter for Democratic nominees, endorsing Obama in 2008. But during a 2016 MSNBC appearance, Diddy criticized Barack Obama for not doing enough for the black community and told black people to “hold their votes” until Hillary Clinton addressed their community directly.

Like Usher, his tune changed completely weeks before the 2020 election. In late October, he took back what he said about the Democrats and gave Joe Biden his full endorsement.

“The number one priority is to get Trump out of office,” he said.

Many are wondering if Diddy became too comfortable in his position of power and if speaking freely against the Democratic party led to his downfall. “Diddy” wasn’t as easy to control as “Puff Daddy,” the friendly young talking head leading the early 2000s “Vote or Die” campaign, a program marketed behind the scenes by Democrat Alexis McGill, CEO of Planned Parenthood, who spoke at the 2024 DNC.

---

Usher and Pink’s X Accounts Wiped

On September 22, a few days after Diddy was denied bail, 7000 tweets from Usher’s X feed vanished, and many starting accusing the singer of removing any incriminating evidence linking him to Diddy’s crimes.

“Account got hacked and damn y’all ran with it!” Usher wrote on X after fans started questioning this timing, blaming it on a hacker.

A few days later, on September 26, 4000 of Pink’s tweets vanished. Both artists are products of L.A. Reid both signed to Arista Records back in the day.

Pink denied being associated with Diddy and put out a public statement, ““I don’t know why I became a headline this week, but I wiped my Twitter account on February 6!!!” she wrote. “There is no truth to the rumors spread this week, and while I’ve met people in passing, I’m not associated with any of the people mentioned.”

Prior to these tweets getting deleted, Elon Musk retweeted an old tweet he wrote in December 2022, calling Twitter both a social media company and a crime scene.

Pink was one of headliners at the 2024 DNC. While Pink’s always been a vocal Democrat, it’s still worth pointing out that two of L.A. Reid’s biggest success stories have endorsed Kamala Harris this election and were also called out for deleting thousands of tweets the same week.

It’s obvious Usher knows a lot more than he’s letting on but like Kanye West said in 2022, “all celebrities are controlled.” Unless Usher willingly steps out of line and is ready to lose it all, we won’t be hearing his side of the story anytime soon.

Who knows what is being held over his head and what could be strategically leaked soon. As we get closer to the election, keep an eye it for more A-list endorsements.

16 days…

A lot can happen in 16 days…

---

Coming Up Next: “The Rat Pack:” Diddy, Jamie Foxx and Ashton Kutcher, How Michael Rubin Took Over Diddy’s Lavish “All White Party” and more