Celebrity
Sean ‘Diddy’ Combs’ assistant said his boss rarely spent a night alone. He shared why he thought Combs wanted constant companionship.
Sean “Diddy” Combs’ assistant believes the disgraced mogul feels a great deal of insecurity. He once said that in the time he worked for Combs, he spent the night alone only a handful of times. His assistant believed Combs made himself feel “macho” by spending time with women.
Sean ‘Diddy’ Combs’ assistant once said he often surrounded himself with women
According to former assistant Phil Pines, Combs was “never alone.” Pines believed the constant presence of overnight guests gave Combs confirmation he was a “macho alpha male.”
“My observation was that a woman made him feel like a man,” Pines said in the docu-series The Fall of Diddy (per Rolling Stone). “And always having somebody around [made him] feel like that. That was kind of his insecurity, in my experience.”
Pines said the constant stream of overnight guests started to seem like a problem to him.
“I never saw him sleep alone,” Pines said. “In two years, I think it was maybe seven to eight times when he would sleep by himself, and I started to kind of put it together that there was something wrong. Like, he needed somebody with him to make him feel comfort. And it was always a guest.”
His assistant recalled a woman once seemed ‘shaken’ by her experience with Combs
Combs’ defense has repeatedly stated that Combs only ever engaged in consensual sex. Pines cast doubt on this, though.
“Anybody who’s ever interacted with [Combs] in that setting, in those relationships, needs to be talked to [to] see how they truly felt,” he said. “I imagine there’ll be tons of people who will respond to that not in favor of the defense.”
He recalled once driving a woman home after one of Combs’ “Wild King Nights.” He said she looked “shaken.”
“I don’t know what took place,” Pines said. “All I can say is that when I brought her down to the car, she was shaking … she was obviously exhausted. She said something to the effect of ‘I’ve never done anything like this before.’”
An interviewer believed Sean ‘Diddy’ Combs’ boasted to cover up his insecurity
Writer Tressie McMillan Cottom profiled Combs in 2021 and recalled his constant boasting, though she didn’t think there was much truth to it.
“He kept talking about, ‘I’m an attractive young man,’” Cottom told The Independent. “The way he would describe himself, first of all, was ‘young’ which I thought was bizarre. It was telling that he has created a character version of himself that is powerful and sexy and physically attractive when really, what he is, is rich.”
She believed his words covered up fear and insecurity.
“Absent the money and the star power, I’m not sure we would look at him and think those things, but that’s the kind of story a very scared, self-conscious little boy would write about himself, right?” she said. “The ladies love me. I’m so powerful. I’m so dope. I’m a playboy. That sounded like a child.”
How to get help: In the U.S., call the RAINN National Sexual Assault Telephone Hotline at 1-800-656-4673 to connect with a trained staff member from a sexual assault service provider in your area.
