Alex Chester-Iwata was only 13 years old when she first met Sean ‘Diddy’ Combs.
She was one of four members of a budding pop girl group when they crossed paths with the Bad Boy mogul at a Nickelodeon event in the late 1990s.
Other young stars from Usher to Ariana Grande were also present, and the teenagers were keen to make a good impression in the hopes of someday securing a record deal under Combs’s label.
Instead, it was Combs who left a lasting impact on Chester-Iwata.
‘I thought he was kind of creepy,’ she told the Daily Mail. ‘To be perfectly honest, I didn’t have the best vibes from him.
‘Honestly, I always was very much like, “This just didn’t feel good to me.” But, you know, we didn’t have the vocabulary to express that.’
Chester-Iwata, along with fellow members Holly Blake-Arnstein, Ashley Poole and Melissa Schuman, spent the next three years in a development program to eventually join the Bad Boy roster.
The journey was a grueling physical and psychological rollercoaster. The teens were subjected to strict diets, brutal workouts, punishing choreography rehearsals and 12- to 14-hour recording days, she claimed.
Chester-Iwata said the regimen left lasting scars on the girls, some of whom have said that they struggled with eating disorders and other emotional trauma.
‘I have been in therapy for almost 10 years,’ Chester-Iwata, now 40, said. ‘I’m proud of where I’ve come and who I am now, but it’s taken a while.’
Alex Chester-Iwata said it took years to recover from the trauma she experienced during her time as a member of Dream, an all-girls pop teen group that went on to work with Sean ‘Diddy’ Combs in the late 1990s to early 2000s
Diddy (center) signed Dream to his Bad Boy Records label in 2000. Dream members, from left to right, Melissa Schuman, Holly Blake-Arnstein, Ashley Poole and Chester-Iwata are pictured at MTV’s Big Help concert in 1999
Before meeting Combs, the group were initially called First Warning and signed with record label ClockWork Entertainment and 2620 Music.
It was then that the girls were introduced to music producers Vincent Herbert and Kenny Burns, who had close ties with Combs.
They were then rebranded with a new band name: Dream.
The two producers revamped the quartet’s clean-cut image and bubblegum lyrics with a sharper, sassier edge.
‘I was just really so impressed because they were so small and they were so young,’ Combs said of the girls in a November 2000 interview with MTV’s Ultrasound. ‘I was like, “Wow, these girls are really talented.”‘
But that’s when things took a grim turn, Chester-Iwata claimed.
She said their days from then onwards included hours of physical training and recording sessions plus monitored and regimented meals.
The girls, 13 and 14, were told to avoid carbohydrates and eat only boneless and skinless pieces of chicken with some vegetables, she recalled.
‘Every day, we had a personal trainer come in, and we would run six miles,’ she said. ‘On top of everything else, they would also weigh us and then they would allocate what we could and couldn’t eat.
‘So sometimes they just wouldn’t feed us but, on top of that, we would have eight to ten-hour rehearsals, singing and dancing. After we got done with recording, we’d have to go to dance class at night.’
When they complained, the girls were yelled at, Chester-Iwata said. Although a child actor since the age of five, she didn’t understand why young girls should need to restrict their diet.
Despite never weighing more than 105lb as a teenager, she recalled being shamed for not being able to fit into a short skirt.
Music executive and producer Vincent Herbert is credited with bringing together Dream’s sound. He has worked with top artists, including Aaliyah, Toni Braxton, Destiny’s Child and Lady Gaga, and his ex-wife Tamar Braxton
Music producer, radio host and entrepreneur Kenny Burns had connections with Combs and brought the teen girl members of Dream to the music mogul’s attention
While the rest of the girls were told to dress more provocatively, Chester-Iwata, who is half Japanese, said she was told to ‘play up’ her heritage by dyeing her naturally brown hair jet black and wearing Asian-inspired clothing.
She also claimed that the management team used the girls’ insecurities to foster competition and rivalry between them.
‘If you weighed a certain amount and if you looked a certain way, we were praised,’ she said. ‘So, it was definitely this type of, you know, teaching us this behavior that we needed to be the skinniest, and we had to have the six-pack [of abdominal muscles].
‘We were 13 and so, you know, to be reliant on the love that they were giving us, and then to feel like we were the ones wronged when we didn’t live up to their expectations. If we weren’t skinny enough, if we were tired, if we were hungry – those were all big no-nos.’
In a January 2022 interview with The Nonstop Pop Show, Schuman described the environment as toxic.
‘We were forced to lose a lot of weight,’ she said. ‘I know for me, it got to be where it was borderline anorexia nervosa. It was bad.’
Chester-Iwata’s mother, Jacquie, said she was concerned for the teens. She made sure that her daughter had food when the managers weren’t monitoring them, and even pushed to make sure they received daily academic tutoring.
When Herbert insisted that the girls all live together, Jacquie said she put her foot down and said no. It was also allegedly suggested by Herbert and Burns that the girls emancipate themselves from their parents, she said.
Jacquie, an attorney, said she was labeled as the ‘problematic parent’.
During this time, Herbert was working with breakthrough acts such as Destiny’s Child and 98 Degrees. Jacquie recalled a conversation with Mathew Knowles, Beyoncé’s manager and father, who gave her some advice.
‘The girls were going to watch Destiny’s Child rehearse and I wanted to make sure they were OK,’ Jacquie said. ‘But [Knowles] told me to stay in the car with him. He told me what I should and shouldn’t be doing, and to just let Alex do what they wanted her to do.’
When she rejected the instruction, Knowles allegedly turned his back on her.
‘He was just another man in the industry telling me what I should do and to let them have control over my daughter,’ Jacquie told the Daily Mail. ‘That was never going to happen.’
After years of training, Dream was flown from Los Angeles to New York in 2000 to perform for Combs and the Bad Boy Records team. It would be the final test before the group was to be officially signed to the label.
Since their management controlled the girls’ every move, Jacquie surreptitiously gave her daughter a burner cell phone in case of an emergency.
Mathew Knowles (center) with Destiny’s Child
Combs’s Bad Boy Records added pop girl group Dream to its primarily hip-hop and R&B roster of artists. It’s known for launching the careers of prominent artists such as The Notorious B.I.G., Mase and Faith Evans
The girls, then aged 14 and 15, sang ‘Daddy’s Little Girl’ to Combs and his staff in the Bad Boy office in Manhattan.
‘Looking back, it sounds kind of creepy now,’ Chester-Iwata said of the song choice.
The group received Combs’s final approval and were promised a contract, becoming the first pop girl group in Bad Boy’s roster.
To celebrate, they were whisked away to the famous Russian Tea Room, where Chester-Iwata said the girls were paraded around the restaurant.
The next day, Dream were flown home to Los Angeles where they were then expected to sign their contracts.
But, on receipt of the documents, Chester-Iwata said they were discouraged from consulting with an outside attorney.
‘I told them we weren’t signing until I get an entertainment attorney,’ Jacquie said. ‘I guess the other parents met with Vincent and that’s when they decided that Alex was going to be out of the group.’
Burns and Herbert released Chester-Iwata from her existing contract and paid her off before she was able to sign with Bad Boy Records.
Chester-Iwata with her mother, Jacquie, and husband Matt Blank. Jacquie told the Daily Mail that she was labeled as the ‘problematic parent’ when pushing back on decisions by Dream managers that gave her cause for concern about the health of her daughter
Dream’s video for the song ‘Crazy’ was an edgier and more sexy presentation of the group. Some of the members said they did not feel comfortable with their provocative look on the video
While disappointed, Chester-Iwata was also relieved.
‘It was a big moment for us all but my mom saw I was deeply unhappy,’ she said. ‘The relationships between the four of us girls were really strained because you’re being pitted against each other.
‘Who’s the prettiest? Who’s the skinniest? Who’s the most vocally talented? You definitely had the girls just fighting against each other.
‘If this happened today, I’d like to think that us girls would all band together and be like: “F–k you and f–k the system. We’re not doing this. You can’t treat us this way!” But, back then, there were no vocabulary words for this that we knew of.’
Chester-Iwata was replaced by 13-year-old Diana Ortiz, and Dream signed with Bad Boy.
Schuman said in The Nonstop Pop Show interview: ‘We were essentially forced to sign the contract under duress. They said if you don’t sign this contract, we will replace your daughter. And that’s actually how Alex got cut.’
Dream’s He Loves U Not became a hit single in the summer of 2000, peaking at No 2 on the Billboard Hot 100 chart. They opened for artists such as 98 Degrees and Britney Spears, and released their debut album It Was All a Dream, which went platinum.
Despite the success, Schuman said she was unhappy and wanted to leave but claimed that the only way to break her Bad Boy contract was by agreeing not to release her own music.
‘I wasn’t happy in the group for a very long time,’ Schuman said. ‘It wasn’t a hard thing for me to decide because I knew what was best for me. I felt it wasn’t healthy and, as much as I loved it, at the same time there was a lot of unhealthy dynamics that was just not OK.’
Combs announced her departure from in April 2002 on MTV’s Total Request Live show, saying that Schuman was pursuing acting instead and there were no hard feelings.
Dream lasted three years under Bad Boy Records
After leaving Dream, Chester-Iwata (center) went on to pursue a successful acting career on Broadway and TV. She is also an activist and the creator and editor-in-chief of the online media platform Mixed Asian Media
‘That was not true,’ Schuman said in an interview. ‘I was leaving the group because I was unhappy, and an acting career was the only other medium at the time that I could think of to springboard off of because I wasn’t allowed to pursue music.’
Schuman was replaced by 15-year-old Kasey Sheridan, and the group began working on the follow-up album, Reality, under Combs’s direction.
He pushed them to record a new song called ‘Crazy’ and a music video, neither of which the girls liked.
‘I was told by Puffy that I needed to lose eight pounds for the video, and I was being worked really hard by trainers,’ Sheridan said in an interview featured in the April 2024 YouTube documentary, The Dark Side of Dream.
‘I was being overworked; I was undereating. It felt like all eyes were on me all the time, I was binge eating when I was alone.’
In interviews over the years, Dream members said the video was over-sexualized, showing them dancing seductively in skimpy outfits.
‘I wasn’t comfortable with it,’ Ortiz said. ‘I felt like I was asked to do something I did not want to do.’
Dream would last only three years under Bad Boy after Combs’s label shelved the second album, disbanding in 2003 due to rising tensions and creative conflicts.
Herbert, Burns and Knowles have not responded to the Daily Mail’s requests for comment.
A spokesperson from Combs’s camp denied the former Dream members’ allegations against the Bad Boy mogul and the label.
Combs, who is in the middle of a federal criminal trial in Manhattan for unrelated charges of racketeering conspiracy, sex trafficking and transportation to engage in prostitution, could face decades in prison if convicted.
His spokesperson told the Daily Mail: ‘This is nothing more than a made-up story, timed to coincide with Mr Combs’ legal proceedings and to generate headlines.’
Chester-Iwata said she felt fortunate that her mother constantly fought for her. She reconnected with her former bandmates, who told her they still had not received any royalties from the work they did under Bad Boy.
‘I definitely had a better deal, leaving and being bought out of my contract versus them,’ Chester-Iwata said. ‘They’ve all said that I had a better deal.
‘I’m not surprised because it’s the music industry. The way high-powered men treat women is appalling or treat people in general who they think they control.’
For young artists who want to break into the music industry, Chester-Iwata had this advice: ‘Advocate for yourself. Trust your gut and, if something doesn’t feel right, speak up.’
