Aaliyah: Married Illegally at 15, Drugs, Corruption, and a Fiery Crash

Summary

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DISGRACELAND – Aaliyah: Married Illegally at 15, Drugs, Corruption, and a Fiery Crash

Air date: November 12, 2024
Host: Jake Brennan
Production: Double Elvis

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Episode Overview

This episode dives into the life, music, and tragic death of R&B icon Aaliyah, exploring not only the surface details everyone knows—from her meteoric rise to stardom and infamous partnership with R. Kelly, to the plane crash that took her life—but also the shadowy network of corruption, criminal negligence, and conspiracy rumors that lurk behind the headlines. Host Jake Brennan brings his signature reverence-meets-recklessness storytelling style to the legacy and loss of a star who was, in many ways, just getting started.

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Key Discussion Points and Insights

1. Early Life, Talent, and Family Influence

• Aaliyah’s Early Brilliance:
  From her first performance on Star Search at age 10, Aaliyah’s rare natural “fire” was recognized by industry veterans like Ed McMahon.

  “The fire burned inside you, independent of outside influence.” – Ed McMahon, as recounted by Jake Brennan (04:57)

• Family Connections:
  Her aunt, Gladys Knight, helped launch her career, showcasing how Aaliyah was “groomed”—a term Brennan acknowledges is weighted, and purposefully ambiguous—for showbiz from an unusually young age.

  “It sounds weird in 2024 to say that Aaliyah was groomed, but that’s exactly what was happening throughout her childhood.” (06:09)

2. Aaliyah and R. Kelly: Manipulation and Illegality

• The Predatory Partnership:
  At just 14, Aaliyah records her debut album with R. Kelly—produced and largely written by him—including its pointedly titled “Age Ain’t Nothing But a Number.”
  • R. Kelly, then 27, not only collaborated musically but secretly married Aaliyah at age 15, using a fake ID acquired through bribery.

  “R. Kelly played the part of the predator… produced Aaliyah’s first record, which, yes, bears the unfortunate title Age Ain’t Nothing But a Number…Just a few months after the album’s release…R. Kelly secretly married Aaliyah, who was then 15. Just 15.” (07:58)

• Family Intervention:
  Her parents annulled the marriage in February 1995, after which Aaliyah made a concerted effort to distance herself from R. Kelly—and the controversy.
• Enduring Trauma and Silence:
  Allegations abound—possible pregnancy and abortion, and ongoing silence.

  “She denied the whole thing had ever happened. Not because it didn’t happen for real, because she was moving on.” (10:36)

3. Reinvention and Creative Independence

• Breaking Away & Musical Evolution:
  Aaliyah sought out creative autonomy through her partnership with Missy Elliott and Timbaland, whose innovative production style on One in a Million helped her “wipe the slate clean” and redefine her sound.

  “Aaliyah took a chance on Virginia natives Missy Elliott and Tim Mosley, aka Timbaland, while many others would not, and the chance paid off.” (19:28)

• Hollywood Ventures:
  She transitioned to acting, performing her own stunts in Romeo Must Die and heading to Australia for Queen of the Damned while continuing to record music.

4. The Final Days: Pressure, Fatigue, and the Fatal Flight

• Reluctance and Exhaustion:
  Aaliyah was uneasy about flying and wanted to return home quickly but felt pressured by work commitments. Phone calls with boyfriend Damon Dash and production team underscored her inner conflict.

  “She hated flying. She hated planes. She was the utmost professional. Despite her personal reservations, she wasn’t going to rock the boat.” (05:55)

• Drug Use for Relief:
  Before boarding, a young baggage handler witnessed someone offering Aaliyah a pill to help her rest, with the implication that she was unconscious when boarded.

  “She just needed to rest. Someone offered her a pill. Yes, please. Anything to take the edge off.” (13:05)

5. The Crash: Chain of Negligence and Corruption

• Timeline of Disaster (Bahamas, August 25, 2001):
  The overloaded plane—carrying Aaliyah, her crew, and heavy luggage—crashed almost immediately after takeoff.

  “After just 60 seconds, some 100ft in the air, the plane suddenly veered to the left, way off course…and the Cessna was in a free fall, straight down…the wreckage was in flames.” (31:20)

• Investigation Exposes:
  • The pilot, Luis Morales III, was fresh off a felony plea, found with alcohol and cocaine in his system after the crash, and wasn’t certified for the flight.
  • The airline, Blackhawk International Airways, had a rap sheet for cutting corners, failed safety protocols, and its owner Gilbert Chacon had a separate $400M fraud conviction.
  • A last-minute switch from a safer air charter provider (Skylimo) to Blackhawk is surrounded by unanswered questions.

  “Overloading and engine failure quickly took a back seat when new revelations came to light... illegal drugs, and massive fraud. The kinds of things that make a plane go into a nose dive after takeoff.” (32:44)

6. Conspiracies, Lawsuits, and the Aftermath

• Rumors and Suspicions:
  The circumstances fed a range of public theories:
  • Mary J. Blige called it “spiritual murder.”
  • Jaguar Wright has publicly blamed Jay-Z, while others speculate about Lenny Kravitz’s offer of a private jet being usurped by director Hype Williams.
  • Damon Dash (Aaliyah’s boyfriend) claims he knows the truth, but won’t reveal it.

  “I know what happened, but I’m not going to tell you what the truth is. At this moment, we’re in public.” – Damon Dash (40:04)

• Legal Fallout:
  Aaliyah’s family sued numerous parties for wrongful death and settled quietly out of court.

  “One year after the lawsuit was filed, the family settled with Black Hawk Sky Streaming in Chacon for an undisclosed sum. The details of that settlement are confidential.” (41:55)

• Community Impact:
  Singer Maxwell paid for Aaliyah’s funeral when the label failed to honor a promise. The industry ripple effect, and especially the tragedy of wasted potential, is a recurring theme.
• Legacy:

  “The incredible talent, the fire that burned deep in the heart and soul of Aaliyah, that’s in the public record. The fact that that public record only lasted until 2001, now more than 20 years in the past, when Aaliyah Haughton was just getting started, that’s a disgrace.” – Jake Brennan (42:23)

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Notable Quotes & Memorable Moments

• On Early Talent:
  “You weren’t taught it. You didn’t get it from your parents… the fire burned inside you, independent of outside influence.” – Recalling Ed McMahon’s words (04:57)
• On R. Kelly:
  “If the lyrical content R. Kelly was getting Aaliyah to sing wasn’t troublesome enough, the fact that the teenager and the grown man were much more than a musical partnership absolutely was.” (08:33)
• On Reinvention:
  “This new record was Aaliyah’s chance to wipe the slate clean, to reintroduce herself to the public, and the first step in this new creative direction was to hire a new production duo out of the dirty cell.” (19:20)
• On the Fatal Crash:
  “The plane dropped like a stone within seconds, crashing into the marsh… It exploded upon impact and the wreckage was in flames.” (31:36)
• On Industry Responsibility:
  “Virgin also failed to honor a verbal promise to pay a Nassau mortuary to prepare the bodies of Aaliyah and other passengers. Ultimately, the RB singer Maxwell stepped up to foot the bill for Aaliyah’s funeral.” (41:39)
• On Lasting Legacy:
  “The fact that that public record only lasted until 2001…when Aaliyah Haughton was just getting started, that’s a disgrace.” (42:22)

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Timestamps for Key Segments

| Time | Segment / Topic | |-----------|------------------------------------------------------------------------| | 03:53 | Episode setup: Aaliyah, her drive, illegal marriage, drugs, crash | | 04:51 | Aaliyah’s early TV appearances and natural talent | | 06:05 | Family background; mentorship by Gladys Knight | | 07:58 | Meeting R. Kelly; underage marriage scandal | | 10:36 | Aftermath of annulment and her silence | | 13:05 | Final day in Bahamas; exhaustion and the pill | | 18:25 | High school balancing act; reinvention with Timbaland & Missy | | 19:20 | One in a Million and unique sonic direction | | 21:41 | Creation of “Are You That Somebody” | | 25:55 | Third album and creative peak | | 29:07 | Lead-up to crash: weight/disagreements, fatigue, reluctance | | 31:20 | Crash details and immediate causes | | 32:44 | Corruption: pilot and airline criminal records | | 35:02 | Alternate theories & conspiracies: Mary J. Blige, Jaguar Wright, Dame Dash | | 40:04 | Lawsuit & settlement, Maxwell pays for funeral | | 42:22 | Jake Brennan's closing remarks on legacy and loss |

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Overall Tone and Style

• Language: A mix of hard-hitting and reverential, with flashes of dark humor (e.g., “Sorry. Had to do it.” when referencing “rocking the boat”).
• Delivery: Fast-paced, investigative, dramatic, and speculative—staying true to the Disgraceland brand of true crime-infused music history storytelling.
• Point of View: A deep empathy for Aaliyah, harsh scrutiny for those who enabled harm and profited from her, and skepticism toward unsolved mysteries and “hidden truths.”

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Conclusion

Jake Brennan’s episode on Aaliyah presents a compelling, tragic portrait of an extraordinarily gifted artist ensnared by predators, betrayed by negligence and systemic failure, and lost long before her legend could fully flourish. The narrative captures the collision of innocence, ambition, and the dark side of stardom, urging listeners to remember not simply the drama, but the loss of an authentic talent—one whose creative fire still resonates more than two decades after her untimely death.

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To hear more, visit: disgracelandpod.com

Transcript

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[Jake Brennan]

Change hey guys, Our Aaliyah episode this week is a story of the tragic R B singer's death and the tragedy that has been recorded to history. That is. This isn't a story that dives deep into the recent wild allegations involving Sean Diddy Combs and Jay Z relative to Aaliyah's death. Those rumors have not been proven out by anything factual yet. If you want more on the validity of these allegations, I'm going to get into it a little bit in this upcoming after party. That'll be the next bonus episode that drops right after this one in your feed. In the meantime, here's our story on Aaliyah and her relationship with R. Kelly and her demise. Hope you dig it.

[Ryan Seacrest]

This episode contains content that may be

[Jake Brennan]

disturbing to some listeners.

[Ryan Seacrest]

Please check the show notes for more information.

[Jake Brennan]

Disgraceland is a production of Double Elvis. This is the story of a pop star, an incredible talent, Aaliyah, a talent whose creative fire burned from deep within. But it's also the story of R. Kelly and an illegal marriage. It's about drugs, corruption, it's about wild a list accusatory conspiracy theories. And it's a story about a fiery crash and about great music. Unlike that music I played for you at the top of the show, that wasn't great music. That was a preset loop for my melotron called Instant Theme Song MK1. I played you that loop because I can't afford the rights to Fallen by Alicia Keys. And why would I play you that specific slice of Empire State of Mind cheese? Could I afford it? Because that was the number one song in America on August 25, 2001. And that was the day that a plane carrying Aaliyah and eight others crashed shortly after takeoff in the Bahamas, killing all on board. On this episode, an illegal marriage, drugs, corruption, conspiracy theories, a fiery crash and Aaliyah, I'm Jake Brennan and this is Disgrace. August 25, 2001 if only the mind of 22 year old Aaliyah Haughton was as clear as the blue skies here in the Bahamas. The sun, the sand, the weather was all perfect. Everything else was. Well, it was complicated. Aliyah didn't want to be here in the first place. Which sounds crazy because here, specifically in the Abaco Islands, was more than one person's idea of paradise. For Aaliyah, it was work. Leading a team of dancers on a catamaran out in the ocean, wrapping the video shoot for Rock the Boat, the second single from her recently released self titled album, her third album overall. But though it was work, it wasn't Aaliyah's vision. The vision belonged to Hype Williams, arguably the most in demand director when it came to music videos for the hottest hip hop and R and B artists. When Hype insisted they leave Miami for the Bahamas, Aaliyah expressed her displeasure. She hated flying. She hated planes. She was the utmost professional. Despite her personal reservations, she wasn't going to rock the boat. Sorry. How to do it. There were fights to fight and hills to die on, and Aaliyah knew that this wasn't one of them. So she got her nerves under control, got on the plane and went to the Bahamas, all the while maintaining that quiet, reserved demeanor she was known for, the same demeanor that simmered on low behind a pair of dark shades or her trademark peekaboo hairstyle, those long strands covering one of her eyes like Veronica Lake, her mother's favorite actress. Under that quiet reserve, however, was the fire. Or so said Ed McMahon, one time host of Star Search, a hugely popular TV talent show in the 1980s and 90s. When Aaliyah appeared on the show in 1990 to perform Rogers and Hart's My Funny Valentine at just 10 years old, Ed McMahon, the longtime Tonight show sidekick to Johnny Carson, saw the fire in Aaliyah before she even sang a note. You weren't taught it. You didn't get it from your parents, McMahon said. The fire burned inside you, independent of outside influence. For Aaliyah Haughton, that fire burned bright and hot. Her parents knew this. They worked tirelessly to secure opportunities for their daughter to perform. Her Auntie Gladys knew this too. That's Gladys, as in Gladys Knight and the Pips, by the way, Aaliyah's aunt by marriage to her mom's brother. And it was that famous aunt who brought her 11 year old niece up on stage to sing with her for all five of her sold out shows at Bally's in Las Vegas. It Sounds weird in 2024 to say that Aaliyah was groomed, but that's exactly what was happening throughout her childhood. She was a megawatt talent from a very young age who was groomed by everyone around her in order to make her a star. Of course, there are gross connotations with the word groomed, and for good reason, because the next person to groom Aaliyah after Star Search and her parents and her Auntie Gladys was R and B superstar R. Kelly, who, when Aaliyah was just 14 years old, a freshman at Detroit High School for the Fine and Performing Arts, majoring in dance, played the part of the predator Svent Gali. As Aaliyah's professional career was just taking off, R. Kelly wrote and produced Aaliyah's first record, which, yes, bears the unfortunate title Age Ain't Nothing But a Number. Unfortunate because, again, Aaliyah was 14 and R. Kelly was 27. If the lyrical content R. Kelly was getting Aaliyah to sing wasn't troublesome enough, the fact that the teenager and the grown man were much more than a musical partnership absolutely was. Just a few months after the album's release in the summer of 1994, R. Kelly secretly married Aaliyah, who was then 15. Just 15. And he did so by paying off a state employee to create a fake ID that showed that she was 18. But as our guy Kurt Loder pointed out when he broke the news on mtv, R. Kennedy Kelly wasn't fooling anyone, because earlier that year, Aaliyah was dropped from the Budweiser Superfest tour precisely because she was a minor. Based on what we now know about R. Kelly and his decades of sexual abuse and child pornography, one can only imagine that what went on between him and his child bride behind closed doors was. I don't even want to go there. If you're looking for a deeper dive into that whole saga, check out our episode on R. Kelly and the Disgrace in Archive. But I'm getting away from the story here. At least one of R. Kelly's victims has claimed that he got Aaliyah pregnant and made her get an abortion during their time as husband and wife. But Aaliyah wasn't talking about it. Not then and not ever. Once her parents stepped in to annul the marriage in February of 1995. Whatever spell R. Kelly had cast over an innocent and impressionable Aaliyah was broken. She didn't just walk away. She denied the whole the whole thing had ever happened. Not because it didn't happen for real, because she was moving on. She didn't wish death upon anyone but still keep that man away from her. Which was easier said than done. R. Kelly's crimes were practically being perpetrated out in the open, but no one was calling him on it. Aaliyah's own uncle, Barry Hankerson, the one who was married to Gladys Knight, was a music business insider who continued to work with R. Kelly for years after his death niece's illegal marriage. And then there was Hype Williams, the director of Aaliyah's Rock the Boat music video here in the Bahamas. Hype worked with everyone in hip hop and R and B, including R. Kelly, with whom Hype had made and was continuing to make a ton of content. Aaliyah was a force of nature, street but sweet as she called herself. But her power wasn't to wipe R. Kelly from the face of the earth, it was to lift herself up. And she did this by following her own gut and by doing things her way, taking a chance on an unknown and unorthodox music production duo. More on that in a bit. Performing all her own stunts in her movie debut, Romeo Must Die, a month of training to learn one scene, she went the distance, literally all the way to Australia to film her next movie, Queen of the Damned, while simultaneously recording tracks for her new album. At night she was creatively reborn as an inspired multi hyphenate and she worked her ass off for it. But right now Aaliyah was done with work and she wanted to go home. She stood anxiously at the Marsh harbor airport there in the Bahamas, the island breeze blowing through her hair and she stared down the Cessna twin engine plane that was currently being loaded up with luggage. It would soon bring her back to the mainland, back to normaly, back to her boyfriend Damon Dash, co founder with Jeff Jay Z of Rockefeller Records. This plane, though it wasn't big like the one that had brought her out here. It was a puddle jumping little piece of it was supposed to carry her and her bodyguard and her makeup artist, two hairstylists, a Virgin Records executive, two employees of Blackground, her uncle's record label and the pilot, plus all their stuff. She worried it was just too much, too heavy. She called Dame. He told her to wait, he'd send a private, private jet tomorrow to bring her home. She wasn't sure. She just wanted to see him and both of their schedules were crazy. Over the next few weeks, if she wanted some quality time with him, she had to go. Now she was conflicted, exhausted. The baggage handlers packed in. The plane, heard her concerns over the wait. They said they'd remove some of the stuff and lighten it up. That was helpful. But now she had a headache. She just needed to rest. Someone offered her a pill. Yes, please. Anything to take the edge off. One of the baggage handlers, just a kid really, helping out with the family business, handed her a glass of water to wash the pill down. He was like 13, 14 years old. Something like that reminded her of when she was that age. Figuring it all out, making mistakes, finding her way. Street but sweet. And within minutes, she was out. The dream she had was the same one she'd been having all week. It was dark, pitch black. She couldn't see anything. She was scared. She was running. Something was after her, chasing her. Her heart was pounding, her legs ached. And then suddenly she took off. She was flying. She felt free, as weightless as that Cessna was loaded. She didn't want it to end here. Asleep, dreaming, escaping, going to a place where no one could reach her. Alia was untouchable.

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[Jake Brennan]

Life never plays out the way any of us want or expect it to. There's an old Yiddish saying that basically says, man plans, God laughs. Or as John Lennon put it in one of the last great songs that he ever wrote, life's what happens when you're busy making other plans. For Aaliyah Haughton, life happened all the but never in order. Chronological order, that is. Her education at Detroit High School for the Fine and Performing Arts, where she trained as a dancer, was interrupted by her quick fame as a teenager. That meant juggling studies with stardom for four straight years, and that meant working just as hard at maintaining a grounded, normal teenage life as she did working to put out huge records atop the RB and pop charts. By the time her senior year rolled around in 1997, the desire for normalcy was so strong that she made the effort to show up in person to school events as much as she could. She even attended her senior prom wearing a powder blue pantsuit and crop top, a fashion statement that didn't just buck the expectations of what a prom outfit should look like, but one that played a riff on the kind of fashion that she was now modeling for Tommy Hilfiger. Her appearance in the industry giant's wildly successful, successful campaign that year revitalized the hilt figured name by aligning it with RB and hip hop culture while simultaneously elevating Aaliyah in status at age 18. To repeat, when Aaliyah attended her high school prom, she did so while she was already a famous singer and a model on the come up. She was everywhere mtv, bet, the Tonight Show, Showtime at the Apollo, and now in Detroit at school, just trying to be be normal. But there was nothing normal about any of it, just like there was nothing normal about the music she was making. Her second album, One in a Million, released the year prior in 1996, was unlike anything in the R and B world at that time. It wasn't diva music like Mariah, it wasn't baby making music like Boyz II Men, and it was purposefully divorced from the jailbait fantasy once propagated by her infamous example. One in a Million was funky, trippy, a stew of R and B, hip hop and electronica that for some was actually a little too weird. Like, what were those sounds on that track? Were those crickets? A lot of radio stations hesitated to put the title track on air at first because it didn't fit in. Which was exactly the point. This new record was Aaliyah's chance to wipe the slate clean, to reintroduce herself to the public, and the first step in this new creative direction was to hire a new production duo out of the dirty cell. Aaliyah took a chance on Virginia natives Missy Elliott and Tim Mosley, AKA Timbaland, while many others would not, and the chance paid off. The title track from One in a Million went to number one on the R B chart and to number five on the pop chart. More success followed, including Golden Globe and Oscar award nominations in 1998 for her contribution to the Anastasia soundtrack. She couldn't beat Celine Dion in My Heart Will Go on from Titanic. Nobody could. But Aaliyah still made history at age 19 by becoming the youngest artist ever to perform at the Academy Awards. And soon she wasn't just making history. She was making some of the most defining music of the era. Against all odds, Timbaland got the call at 1 in the morning. It was Barry Hankerson, Aaliyah's uncle, Auntie Gladys's ex, owner of Black Ground Records, the label that had partnered with Atlantic Records to release Aaliyah's music. Tim was in la, but Barry was back east in New York, where it was three hours later in the morning, but still way too fucking early. Tim wanted to know what was so important that couldn't wait until tomorrow. Barry told Tim that a huge opportunity just presented itself, that Aaliyah had been offered the lead single on the soundtrack to Dr. Deuce Little, the highly anticipated summer comedy starring Eddie Murphy. But there was a catch. The movie was weeks away from release. They had to produce the track now, tonight, and deliver it by 11am Again, it was 1am out in Los Angeles, 4am in New York. The track was due at 11am Was that East coast or west coast time? Does it fucking matter? My point is that Timbaland and Aaliyah had hours to conceive and record this song that Atlantic Records and 20th Century Fox, the studio putting out the movie, were betting on to be a huge hit and thus sell BOKU soundtrack CDs. Timbaland's first reaction was to push back. He'd just come off stage in Los Angeles and he was exhausted. And now he was expected to turn out a hit song in, what, 10 hours? Barney was out of his mind. They needed more time. But there was no more time. In fact, Barry had bluffed and told Atlantic that they already had a track in the can. There was, however, good money in it. $400,000, which Timbaland and Aaliyah were welcome to split down the middle. And to sweeten the pot, the song was already written and ready to go. It was called Are youe that Somebody? And it was the brainchild of Stephen Ellis Garrett, AKA Static Major, a songwriter and producer who, unbeknownst to most, was currently in a secret relationship with Aaliyah. The promise of a pretty Sweet Payday lit a fire under Timbaland. He put up the bat signal and assembled Aaliyah, static major and Tim's right hand man and engineer Jimmy Douglas at Village Studios over on the west side of la. There they get to work again, flexing the weirdo muscle, the one that drew raised eyebrows and then earned them a coveted number one slot with one in a Million. Timbaland's stuttering beat, the clicks and the clacks and the off kilter inverted funk of it all inspired, and I'm not kidding here, by the Oompa Loompa song in the Willy Wonka and the Chocolate Factory film. That odd sonic place setting was then balanced out so delicately by Aaliyah's compelling vocal, so confident, so cool and collected. The genius of this track, and I remind you that it was created at the last minute in the wee hours of an early summer night turned morning, is how skillfully it balances avant garde and mainstream sensibilities. Perhaps it was difficult to see at the time when it came out on the soundtrack for a second silly Eddie Murphy comedy, but there is something so radical about this track that it's subversive. And I haven't even mentioned one of the song's most indelible elements, which is the sampled sound of that baby cooing during the hook, a sound that Timbaland, in his delightfully strange and subversive way, added at the last minute right before they mixed the master and shipped. Are you that somebody to the label? That baby sound, by the way, comes from a 19644 album called Authentic Sound Effects, Volume 8. And if you think it sounds familiar, his Royal badass Prince had used the same exact sample some 16 years prior at the very end of his song Delirious. But back to the story, the creative partnership between Aaliyah and Timbaland was a crystal ball of sorts, gazing into the future of R B and hip hop. It was coming down the pike at them, and that fact is a bit easier to see now in hindsight, but at the time it was just life happening calls in the middle of the night. Songs whipped together under great pressure, necessity being the mother of invention, all of that. Three years later in 2001, life was still happening, though still not in the way it's expected to happen. God laughing while we're busy making other plans. And so on. Aaliyah and Blackground Records were now partnered with Virgin Records to release her third eponymous album. Timbaland, who was busy with other high profile projects, barely had time to contribute, though Aaliyah was able to corner him to work on three of the album's tracks. The album was poised to level her up once again. The biggest tour of her career was on the horizon, with the goal being to make Aaliyah as much of a household name as Madonna. That was the dream. But first Aaliyah had to wake up from another dream, one she was having at an airport airport in the Bahamas, while she was waiting to fly back home and back to that long lost sense of normalcy.

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Aaliyah may have never woken up from that dream. That dream, by the way. The one I described earlier, in which she is running from something in the darkness. Only the lift off, take flight and escape. She described it as a dream that she kept having when she gave what would turn out to be one of her final interviews to a German reporter in Paris. This was just weeks before she traveled to the Bahamas to shoot the video for Rock the Boat with Hype Williams. Once again, According to the 13 year old luggage carrier who was helping out with his family's business at the Marsh Harbor Airport, the one who saw someone give a pill to Aaliyah before she passed out once it was time to board the Cessna 402B twin engine plane traveling from the Bahamas back to Miami on August 25, 2001. Aaliyah was still asleep and had to be carried onto the plane. Which leads to the obvious, what was that pill? And who gave it to her? But I'm getting ahead of myself. Getting on the plane unconscious may have been the only way Aaliyah would have agreed to do it, seeing as how she had a lot of anxiety about boarding the aircraft in the first place. It was small and she worried it was over the weight limit directly preceding her being carried onto the plane. An argument took place among airport personnel about the total weight of the passengers and their luggage. The pilot was complaining to anyone that would listen, and the back baggage handlers too. There was too much luggage on board one minute and there wasn't too much luggage on board the next. It kept going back and forth. Malia's team, that's her bodyguard, her makeup artist, two hairstylists and three record label employees, were all getting restless. The plane was scheduled to take off at 4:30 in the afternoon. But now it was almost 6 and they were still at a standstill. Tempers flared. The pilot threw up his hands and he conceded he didn't even know what he was arguing about anymore. He just wanted to get his bird up in the air and get these irritated flatlanders back home. It was 6:45 that evening when the Cessna finally boarded, over two hours past its original departure time. The skies were blue. The weather was calm. The plane's twin propellers began to squeak and twirl as the engine fired and then kicked into full speed, the sound like dual supersized lawnmowers burning hot and loud. The passengers settled in as the pilot taxied the aircraft to the top of the Runway and the call came in over the radio that they'd been cleared for takeoff. The pilot increased the throttle and the plane rumbled and sped forward, gaining speed as it traveled down the Runway. More throttle, more rumbling, more speed, and they were airborne. The Cessna grabbed gradually, making the climb from the ground to the clouds. Steady up a little higher, steady and higher, still steady. And then, after just 60 seconds, some 100ft in the air, the plane suddenly veered to the left, way off course. And as it did, the nose began to turn from ascent to descent, from skyward to earthbound, and the Cessna was in a free fall, straight down the plane. Plane dropped like a stone within seconds, crashing into the marsh lined with bushes. It exploded upon impact and the wreckage was in flames. First responders found an aircraft ripped to pieces, the bodies of all seven passengers, as well as the pilot were strewn throughout the crash site. Someone was screaming. Three of the people on board, Aaliyah's bodyguard, her hair stylist, and one other unidentified person Were found alive, Though all three soon died, either at the hospital or on the way. Everyone else was pronounced dead at the scene, Including Aaliyah, who was discovered approximately 20ft from the mangled, smoking twist of steel, Strapped into her seat, curled up, head between her legs, covered in burns with signs of massive head trauma. An investigation into the crash blamed it on engine failure, Adding that as Aaliyah herself suspected, the overloaded cargo and passengers on board could have contributed to that failure. But overloading and engine failure quickly took a back seat when new revelations came to light. Revelations about the pilot, the charter company, illegal drugs, and massive fraud. The kinds of things that make a plane go into a nose dive after takeoff. The kinds of things that ensure that life never plays out the way it's supposed to. Two weeks before he flew, the Cessna that crashed killed Aaliyah, her team, and himself. The pilot, Louis Morales iii, was in a Florida courtroom. He was facing four felonies, including one for possession of crack cocaine. He pleaded no contest. In exchange for that plea, Louis Morales was sentenced to three years probation. Since he was technically not convicted of a crime, his pilot's license was not revoked. All the same, he wasn't supposed to be in the cockpit of that Cessna on August 25, 2001. We know this now because Luis Morales was not listed on the charter plane company's official certificate for the flight. This information was revealed days after the initial crash. It wasn't until close to a year later that an even bigger bombshell was revealed. That being an autopsy report which proved that there was cocaine in and alcohol in Louis Morales body at the time of the accident. Now, Louis Morales wasn't the only one involved in this tragedy who had a record. Blackhawk international Airways, the charter company in charge of the flight, had been fined by the FAA four times in the last three years for violating safety standards, for failing to comply with maintenance standards, and for failing to test its employees for illegal drug use. Even more black holes. Owner Gilbert Chacon had his own criminal record for fraud and not some rinky dink con job either. The guy was part of a huge $400 million insurance scam. His home address was listed as the address of another company called sky street, which was the owner of the Cessna 402B. As all of these facts were revealed to the public in the weeks following the crash, The FAA employee who had cleared the flight took his own life. It gets even more complicated from here. It turns out that Blackhawk wasn't originally hired to charter the flight. That was supposed to have been the responsibility of another company called Skylimo, partnering with a shipment company called Pro Freight Cargo Service. Pro Freight had actually determined that the luggage was heavy enough to require multiple planes to get everyone and everything back to the mainland safely. But when the original flight time had to be rescheduled, someone used that blip in the plan to hastily replace Skylimo with Blackhawk. Someone who? We still don't know. And why? Most likely because Blackhawk was cheaper and cut more corners. Of course, there are other narratives out there about why Blackhawk, a cheapo company with a bad rep, was chosen last minute to bring Aaliyah home. The R and B singer Mary J. Blige, for one, not a close friend of Aaliyah's, but a known acquaintance Speaking on the BET Show 106 and park claimed that Aaliyah's death was not a simple accident, but rather a murder, a spiritual murder. She went on to say, quote, I could go a lot deeper for a lot of people. I would have to bring proof. More recently, there's Jaguar Wright, a singer songwriter who is working with the Roots and Jay Z around the same same time that Aaliyah's star was on the rise in the wake of the recent allegations against Sean Diddy Combs, Jaguar Wright has gone on the offensive publicly. In a series of impassioned interviews that have been circulating on social media, she lays out a conspiracy surrounding Aalyah's death that lays the blame not on Diddy, but instead on Jay Z, the one time business partner of Damon Dash the Roc, a fella executive whom Aaliyah was dating at the time. And look, I'm not even going to touch that one right now. You can go look it up for yourself and see what she has to say. It's wild. And then there's Damon dash, who in 2001 was the love of Aalyah's life and the major motivation for her to return back home on the day that she did. In an interview on Entertainment Tonight, Dame alleged that Lenny Kravitz offered to send a private jet to the Bahamas to pick up Aaliyah. But instead, Hype Williams took that jet, leaving Aaliyah stuck with the whole Blackhawk debacle. When asked if he'd ever confronted Hype Williams about this, Dame replied, fuck yeah. But when pressed to divulge the details of that confrontation, Dame only said, ask him. And just earlier this year, 2024, Dame Dash was talking again about his relationship with Aaliyah and how that immeasurable loss affected both his life and the music world. This time, he was speaking on the PBD podcast. This time, Dame said, quote, I know what happened, but I'm not going to tell you what the truth is. At this moment, we're in public. Maybe that truth will come out in time if there really is a hidden truth behind this great tragedy. Until then, we do know this. In 2002, one year after the accident, Halia's family filed a lawsuit for wrongful death and negligence that named, among others, Blackhawk, its owner Gilbert Chacon, skystream, Hype Williams and Virgin Records. In addition to being accused by one attorney of putting profits over people, Virgin also failed to honor a verbal promise to pay a Nassau mortuary to prepare the bodies of Aaliyah and other passengers. Ultimately, the RB singer Maxwell stepped up to foot the bill for Aaliyah's funeral. But that's another story itself. One year after the lawsuit was filed, the family settled with Black Hawk Sky Streaming in Chacon for an undisclosed sum. The details of that settlement are confidential. But the incredible talent, the fire that burned deep in the heart and soul of Aaliyah, that's in the public record. The fact that that public record only lasted until 2001, now more than 20 years in the past, when Aaliyah Haughton was just getting started, that's a disgrace. I'm Jake Brennan and this is Disgrace Land. All right, guys, thanks for listening to this episode on a list. Leah this week's Question of the week is which child star? This can be a musician like Leah, or it can be an actor, an actress. Which child star has made the Most impact on you? 617-90-66638 Leave me a voicemail. Send me a text with your answer his gracelandpod on the socials. All right, here comes some credits. Disgraceland was created by yours truly and is produced in partnership with Double Elvis. Credits for this episode can be found on the show notes [e-mail] if you're listening as a Disgraceland All Access member, thank you for supporting the show. We really appreciate it. And if not, you can become a member right now by going to Disgracelandpod.com Membership members can listen to every episode of Disgraceland ad free. Plus you'll get one brand new exclusive episode every month. Weekly unscripted material, bonus episodes, special audio collections and early access to merchandise and events. Visit disgracelandpod.com membership for details. Rate and review the show and follow us on Instagram, TikTok, Twitter and Facebook Disgracelandpod and on [e-mail] Disgracelandpod Rocka Rolla. He's a bad, bad man.

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