<p id=”par-1_48″><a href=”https://cheatsheet.com/tag/sean-diddy-combs”>Sean “Diddy” Combs’</a> assistant believes the disgraced <a href=”https://www.cheatsheet.com/music/”>mogul</a> 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.</p>
<h2 class=”wp-block-heading” id=”h-sean-diddy-combs-assistant-once-said-he-often-surrounded-himself-with-women”>Sean ‘Diddy’ Combs’ assistant once said he often surrounded himself with women</h2>
<p id=”par-2_27″>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.”</p>
<p id=”par-3_43″>“My observation was that a woman made him feel like a man,” Pines said in the docu-series <em>The Fall of Diddy</em> (per <a href=”https://www.rollingstone.com/music/music-features/sean-diddy-combs-love-era-trial-cassie-1235249176/” target=”_blank” rel=”noreferrer noopener”>Rolling Stone</a>). “And always having somebody around [made him] feel like that. That was kind of his insecurity, in my experience.”</p>
<figure class=”wp-block-image size-full” id=”emb-1″><img decoding=”async” src=”https://www.cheatsheet.com/wp-content/uploads/2025/01/Sean-Diddy-Combs-parties-2.webp?strip=all&quality=80″ alt=”Sean ‘Diddy’ Combs wears a sequined jacket with icons on it.” class=”wp-image-3764584″><figcaption class=”wp-element-caption”>Sean ‘Diddy’ Combs | Steve Granitz/WireImage</figcaption></figure>
<p id=”par-4_16″>Pines said the constant <a href=”https://www.cheatsheet.com/entertainment/women-sean-diddy-combs-parties-weigh-scale-entering-alleged-party-planner.html/”>stream of overnight guests</a> started to seem like a problem to him.</p>
<p id=”par-5_57″>“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.”</p>
<h2 class=”wp-block-heading” id=”h-his-assistant-recalled-a-woman-once-seemed-shaken-by-her-experience-with-combs”>His assistant recalled a woman once seemed ‘shaken’ by her experience with Combs</h2>
<p id=”par-6_19″>Combs’ defense has repeatedly stated that Combs only ever <a href=”https://www.cheatsheet.com/entertainment/sean-diddy-combs-claims-freak-off-tapes-show-fully-consenting-adults.html/”>engaged in consensual sex</a>. Pines cast doubt on this, though.</p>
<p id=”par-7_43″>“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.”</p>
<p id=”par-8_18″>He recalled once driving a woman home after one of Combs’ “Wild King Nights.” He said she looked “shaken.”</p>
<p id=”par-9_44″>“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.’”</p>
<h2 class=”wp-block-heading” id=”h-an-interviewer-believed-sean-diddy-combs-boasted-to-cover-up-his-insecurity”>An interviewer believed Sean ‘Diddy’ Combs’ boasted to cover up his insecurity</h2>
<p id=”par-10_23″>Writer Tressie McMillan Cottom profiled Combs in 2021 and recalled <a href=”https://www.cheatsheet.com/entertainment/sean-p-diddy-combs-made-grandiose-gestures-like-king-jimmy-kimmel-live-expert-says.html/”>his constant boasting</a>, though she didn’t think there was much truth to it.</p>
<p id=”par-11_56″>“He kept talking about, ‘I’m an attractive young man,’” Cottom told <a target=”_blank” href=”https://www.the-independent.com/news/world/americas/crime/sean-diddy-combs-news-freak-offs-celebs-list-metoo-b2627623.html” rel=”noreferrer noopener”>The Independent</a>. “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.”</p>
<figure class=”wp-block-image size-full” id=”emb-2″><img decoding=”async” src=”https://www.cheatsheet.com/wp-content/uploads/2025/01/Sean-Diddy-Combs-Tupac-1.webp?strip=all&quality=80″ alt=”Sean ‘Diddy’ Combs wears a tan jacket and sunglasses.” class=”wp-image-3760971″><figcaption class=”wp-element-caption”>Sean ‘Diddy’ Combs | Ilya S. Savenok/Getty Images</figcaption></figure>
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<p id=”par-12_9″>She believed his words covered up fear and insecurity.</p>
<p id=”par-13_56″>“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. <em>“The ladies love me. I’m so powerful. I’m so dope. I’m a playboy</em>. That sounded like a child.”</p>
<p id=”par-14_33″><strong><em>How to get help: </em></strong><em>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.</em></p>