Oscar De La Hoya Documentary: The 10 Biggest Bombshells in 'The Golden Boy'

'The Golden Boy' premieres Monday at 9 p.m. ET/PT on HBO.

Spoiler alert! This story contains the biggest bombshells revealed in the two-part HBO documentary, The Golden Boy, set to premiere Monday at 9 p.m. ET/PT, with part two airing the next day. Proceed with caution!

Oscar De La Hoya is laying it all out on the line and opening up about his story, the glories and failures. Directed by Fernando Villena and produced by Mark Wahlberg, The Golden Boy aims to tell the meteoric rise of an East Los Angeles hero who got thrust into the spotlight after bringing home the gold medal at the 1992 Olympic Games in Barcelona.

De La Hoya would go on to struggle with fame and fortune, all of which is magically captured in this two-part documentary. The Golden Boy "peels back the layers of this celebrated yet complicated figure, exploring his triumphs and turmoil to reveal a man struggling to come to terms with lifelong demons and the impossible burden of a nickname he couldn't live up to."

The doc features interviews with De La Hoya's family members, including father Joel De La Hoya Sr., sister Cecilia De La Hoya, brother Joel De La Hoya Jr., and children Atiana, Jacob and Devon. Former fiancee Shanna Moakler, childhood friend/business partner Eric Gomez, ex-trainer Jesus Rivero, boxing promoter Bob Arum, boxing legend Bernard Hopkins and former mistress Milana Dravnel also participate.

Here are the 10 biggest bombshells revealed in the tell-all documentary.

His mother's 'dying wish' was a lie

Oscar said for years and years that it was his mother, Cecilia Gonzalez De La Hoya's, dying wish that he go and win the 1992 Olympic gold medal in Barcelona. He let it slip once during an interview and the quote spread like fire. All these years later, Oscar now admits it was all a fabrication.

He comes clean about it in the documentary, and when asked by ET if he takes ownership of creating that false narrative, De La Hoya says he does.

"I do, because ... when I was getting back from the Olympics, you can imagine. Look, I'm a kid from East L.A., who grew up in humble beginnings," he says. "I was a quiet kid. I was very shy. You [could] barely get a few words out of my mouth. That's how shy I was. So, everything was overwhelming."

"OK, I've accepted that [the narrative], it's now part of me. So, when they're starting to ask questions, 'How does it feel doing it for your mother?' in a way you're now being conditioned. 'OK, let's use that as the narrative. Let's run with that,'" he continues. "And not even thinking [to] myself, 'OK, that sounds great. This is going to be great for my career.' No, it was like, 'OK, that sounds good, actually.' I never thought, 'You know, I can use this to get popular. People will love me.'"

Oscar's brother's first 'I love you' to his mom

The Pride of East Los Angeles says in the documentary he never had the courage to tell his mom he loved her. When he raced to the hospital to be by her bedside before she died from stage 4 cancer in October 1990, Oscar says he got there too late. She had already died.

But Oscar's older brother, Joel Jr., was by her bedside. Joel recalls in the documentary that he told her for the first time that he loved her just before she struggled for her last breath.

Speaking to ET, Oscar explained why the family struggled to express their emotions.

"It’s the culture. My father’s generation, my grandfather’s generation grew up so tough with no emotion," he said. "The typical macho mentality. With my mother, all I wanted was love from her, to hear the words that I love you. Because I wasn’t a bad kid. Maybe if I were to get home late five minutes, s**t, I would get the belt for like five minutes."

"So, I wasn’t a bad kid. That’s what I don’t really understand," he continues. "But now that I’m older maybe it’s frustrations out of her, how she grew up. How her parents treated her. How her grandmother treated her. It all comes down on us. Our generation."

Oscar also told ET that he told his 84-year-old father, Joel Sr. he loved him for the first time just a few years ago. 

Stripper specifically shopped women's clothing for Oscar

Russian exotic dancer Milana Dravnel claimed in the documentary that Oscar once told her during their many drug- and booze-fueled encounters that his mother always wanted a little girl -- before he was born -- and that she would dress him up in girls' clothing and they would sing and play.

"He did mention to me -- I don’t know how much of it is true, maybe it’s all a part of his imagination -- but he told me his mother always wanted a little girl," says Dravnel in the documentary. "So, she would dress him up in little girls' clothes and they would sing around and play. We often dressed up. I would shop specifically for him thinking like, 'This tutu would look great on him. Oh, this fishnet.'"

Dravnel, who was tracked down in Guatemala, explained why Oscar felt safe during their many encounters.

"I understood exactly what he needed. The feminine expression. Being able to be joyful, and playful and childlike," she says in the doc. "All those qualities are suppressed. And he was like, really connected to the feminine [side], especially with me. Some people get drunk and they just want to roll on the floor and do nothing. He wanted to sing, and put on clothes, and pretend and play. And sometimes he would cry. He would break down crying, which most men can’t do."

Oscar says he thought wearing women's clothing would be funny.

"I didn’t feel judged. It was playful. I’m a fighter. I’m a manly guy," he says in the doc. "And it’s like, 'Okay, oh, let me throw this on. Oh, look it’s funny. Oh, yeah, whatever.' It’s like, no big deal."

Shanna Moakler and Oscar De La Hoya: Who broke up with whom?

Oscar recalls seeing Shanna for the first time, describing her as a "beautiful, blonde-haired girl. Tall. Slender." He added that it was like seeing a "silhouette" and "almost like a ghost."

The former boxer recalled Shanna was the "first American that I dated." They would eventually become engaged and welcome a baby girl, Atiana. Shanna recalls in the documentary tagging along to Miami, where Oscar was recording his Latin pop album.

She said they spent time in Miami for three weeks while he recorded his album. But she sensed she was losing him. She claims to have approached Oscar's then-business manager, Richard Schaefer, who allegedly delivered a hint that a breakup was looming.

"I went to set that day. I remember being with Richard Schaefer in the golf cart. I was saying, 'Oscar and I are having some problems.' And he goes, 'You know what, Shanna, I can’t control the heart,'" Shanna claims in the documentary. "And I was like, 'Oh, you son of a bitch. You did it.' That night, Oscar was like, 'Look, I'm gonna go to New York and do [Jay] Leno. I want you to go buy new art for the house, go buy new stuff for the house. And when I come back you and I are gonna start fresh.' So he flew to New York and then he was supposed to come back and I didn’t hear from him."

And that's when she spotted them at the Latin GRAMMYs in the early 2000s-- Oscar and Milagros "Millie" Corretjer, the Puerto Rican singer who -- after being shown a clip of her singing -- inspired Oscar to sing with passion. Oscar says the record label arranged for them to meet, and Millie eventually landed a role in one of his music videos as his love interest.

Oscar offers this explanation.

"When I did take [Millie] to the GRAMMYs, for some apparent reason, Shanna thought I was still with her," he says in the documentary. When asked about the conflicting stories, Oscar admits the timeline of the relationships was pretty close, telling ET, "Yeah, I stick with that. I mean, was it close? It was. But yeah, we were broken up."

But Shanna's not buying it.

"We were together, 1000 percent," she says in the documentary. "The next day, he got in the car with me. I just said, 'Why did you do that?’' He looked me dead in the face and goes, 'I don’t love you anymore.' He goes, 'Shanna, I have more money than God.' And he got out of the car and he came over to the window where I was sitting there balling, and he knocked on the window and he goes, 'Don’t be too hard on me.' Nothing that he said to me was the truth."

Why they really broke up

According to Shanna, Oscar broke up with her because he needed to endear himself to the Hispanic audience in order to promote his self-titled album, Oscar, which was eventually nominated for a GRAMMY for Best Latin Pop Album. He lost to Shakira's MTV Unplugged in 2001.

"Richard told Oscar I wasn't Latina enough and that he needed, in the public eye, to be respected by the Mexican community, to be with a Mexican or Latina woman," Shanna claims in the doc.

It should be noted that Shanna and Oscar are now on good terms. She says as much near the end of the documentary.

"He and I actually went to dinner not that long ago. He said, 'You know, you didn't deserve that,'" she says. "'I'm truly, truly sorry for humiliating you and hurting you.' And it was sincere. It was like I had that glimmer of my friend back. And I hadn’t seen that since he had left me in that car. But I still think he’s a work in progress."

Oscar didn't meet his second son until he was 16

As ET exclusively reported earlier this month, Oscar's owned up to the fact he was an absentee father. In one of the most heartbreaking scenes in the documentary, Oscar's second son -- Devon, 24, from a "one-night stand" with Angelicque McQueen -- reveals how he felt about being the only one who never got to be around his father, even if those hangouts were far and few in between.

"He was like the guy on TV. The guy on my YouTube," Devon says. "He raised me through a screen, almost. It's just hard. You're hanging out with your other children, why not me? Kids would say I’m just some rotten spoiled kid whose father is Oscar De La Hoya and you have everything you want in this world. I had nothing."

Devon ultimately reached out to Oscar on Instagram when he was 16, and they planned a dinner meeting at the MGM Grand in Las Vegas in 2013. Devon said when he saw Oscar, he started balling. He was happy and angry at the same time, adding that he wanted to punch Oscar in the face but also hug him tight and never let him go.

Oscar calls not meeting Devon earlier one of his biggest regrets. Oscar told ET why he was scared about meeting Devon that day.

"It was scary. It was scary. I mean, look, fear takes a hold of us and just changes our life for the good or for the bad. I’ve always been living with fear all my life," he tells ET. "When I met Devon, yeah it was scary. And I wouldn’t have been mad at him if he did punch me. I think I was expecting it. That’s why it was so scary. I didn’t know how his reaction was gonna be. When we did meet it was, we were both nervous, it was odd and awkward, but literally we embraced and started crying."

Oscar didn't tell Millie about Devon 

The boxing camp had to have a very difficult conversation with Millie because he was hiding the fact he had a second son, Devon. The couple was pretty far into their relationship when Milile found out through a gossip magazine.

"She was pissed," he said. "It wasn’t a pleasant conversation, to say the least."

How he orchestrated Atiana and Devon meeting

Atiana and Devon were both headed to watch Oscar fight in Texas. As they boarded the plane, Atiana realized Devon was sitting right next to her. Atiana, in the documentary, expressed confusion as to why Oscar would have them meet this way for the first time.

But their encounter was sweet, and they realized they had tons in common. Once at their hotel, Devon says in the doc that his older brother, Jacob, knocked the door of his hotel room. They were meeting for the first time and they embraced each other.

Oscar tells ET that having Atiana and Devon meet on the plane with seats next to each other was by design.

"I think it was by design. I didn’t know how to be a father. I just didn’t. I didn’t know what that meant," Oscar said. "So, I thought that having them meet and sit by each other they can get to know each other. Luckily they’re very mature and good kids. They’re best of friends. It’s amazing how over the years they’ve been able to forgive. Never forget but to forgive."

His first taste of beer at seven or eight years old

Oscar recalls drinking his first beer at a family party. He said it started with uncles telling you to have a sip. That first sip eventually turned into 30 sips, and that little boy passed out drunk.

He recalls waking up and seeing his late mother's face, "and she slaps the s**t out of me."

Oscar's dad's true feelings about the Chavez-De La Hoya fight

In the documentary, Joel Sr. shockingly concludes that had Mexican icon Julio Cesar Chavez, 33 at the time, been the same age as De La Hoya, 23, when they fought the first time in 1996 for the WBC super lightweight championship, Chavez would have beaten his son. It wasn't until he watched the documentary that De La Hoya says he found out his father felt this way.

"It's disappointing but it's expected," Oscar tells ET. "I didn't know that was his stance. I didn't know that he was convinced that Chavez can beat me if he was younger. That's who he is. I've accepted the fact that he's a tough man. But he’s still my father."

The Golden Boy premieres Monday, July 24, with part two airing Tuesday, July 25 at 9 p.m. ET/PT on HBO. Both episodes will be available to stream on Max beginning Monday, July 24 at 9 p.m. ET/PT.