Big Man on Campus: The Hoops Phenom Who Tried High School Twice

Summary

Chameleon: Big Man on Campus — The Hoops Phenom Who Tried High School Twice

Podcast: Chameleon (Audiochuck | Campside Media)
Host: Josh Dean
Guest: Max Marshall
Date: July 30, 2026

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Episode Overview

In this gripping episode of Chameleon Weekly, host Josh Dean explores the astonishing true story of “Rashawn Richardson,” a 17-year-old basketball prodigy at Dallas’s Hillcrest High School who turned out to be Sidney Gilstrap-Portly, a 25-year-old man reliving his hoop dreams. At the intersection of ambition, deception, and the American cult of sports, this episode unpacks why Sidney faked his way back into high school, how he nearly got away with it, what ultimately exposed his scheme, and the moral complexity behind his choices.

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Key Discussion Points and Insights

1. The Arrival of “Rashawn Richardson” at Hillcrest High

• Setting the Scene (01:32):
  Josh Dean introduces “Rashawn,” a new student enrolling at Hillcrest High amidst the aftermath of Hurricane Harvey. He’s described as tattooed, unremarkably tall, reserved, and supposedly homeless—his records lost in the storm.

  “No one knew anything about Rashawn, really, except that he’d just moved from Houston after Hurricane Harvey… He had nothing. No home, no possessions.” — Josh Dean (02:19)

• Immediate Impact on the Team (03:40):
  Coach Harris, modeled after stern but caring mentors like the film “Coach Carter,” notices Rashawn’s exceptional talent almost instantly.

  “He passes him a ball… shoots, and it’s just like such a more pure buttery shot than, you know, you really see in the Hillcrest basketball gym…” — Max Marshall (03:48)

2. Making His Mark on the Court

• Tournament Breakout (08:51–11:12):
  Hillcrest, normally underdogs, enters a tournament in Louisiana. Coach Harris lets Rashawn take over:

  “Coach Harris basically called a timeout and said, you know what new play, get Rashawn the ball.” — Max Marshall (10:20)
  Rashawn stuns top teams, scores 40 points in three quarters, and draws the attention of college scouts.

• Evolving into Big Man on Campus (11:29):
  Rashawn opens up to teammates, shares his rap tracks, and enjoys his new star status—Hillcrest’s rare “sports star.”

• Season Outcome (12:02):
  Despite Rashawn’s prowess, Hillcrest falls short in playoffs, though he earns “district offensive player of the year.”

  “What everyone saw was a guy who had the trajectory and the skills to play college basketball…” — Max Marshall (12:31)

3. “Rashawn” Vanishes — The Unraveling

• Sudden Disappearance (15:14):
  After winter break, Rashawn doesn’t return. Rumors spread among students.

  “All the students kind of were like, what happened to Rashawn?” — Max Marshall (15:28)

• The Red Flags (15:34–16:34):

  • Odd tattooed initials (“S” and “G”)
  • Selfies taken from “old person” angles
  • Fortnite account under the name “Sidney Gilstrap Portly”
  • A woman with a baby at games—the baby called Rashawn “Dad”

4. The Truth: An Imposter Revealed (16:34–18:03)

• Sidney had previously played high school and college ball. His former coach recognized him at a game, leading to his exposure and arrest for falsifying records.

  “His real name was Sidney Gilstrap Portly… and he was not actually 17. He was a 25 year old with a kid who had already played high school basketball once.” — Josh Dean (16:34)
  “On the face of it. The only illegal thing he did was falsifying government records.” — Max Marshall (17:53)

• The More Serious Offense:
  Sidney also dated a 14-year-old student; he ultimately pleaded guilty to indecency with a child and received probation and sex offender registration.

  “Gilstrap Portly was a 25 year old man courting a 14 year old girl. It’s terrible on any level.” — Josh Dean (18:03)

5. The System: How He Got Away With It (18:59–20:59)

• School administrators were ill-equipped or simply not incentivized to catch frauds, especially those claiming homelessness.

  “Why would anyone ever want to go back to high school?... You're not looking for someone to pretend to be homeless.” — Max Marshall (19:02)

• Sidney blended in amid the chaos and low suspicion; despite being noticeably older, the culture normalized mature, tattooed, and physically imposing teenagers.

6. Sidney’s Motivation — The American Dream and Its Shadows

• Not Glory Days, But Another Chance (21:17–23:31):
  Sidney didn’t seek nostalgia; his rough upbringing, pervasive instability, and failed first act at basketball led him to try again.

  "He felt like it had nothing to do with glory days because there were no glory days the first time around." — Max Marshall (21:17)

• Basketball was Sidney's escape plan from poverty and a troubled family life. He idolized LeBron James and saw basketball as the path out.
• Despite thriving in “street ball,” he never made it big, falling into low-wage jobs as an adult and feeling left behind.

7. The Logic and Lure of the Scam (24:57–26:08)

• Sidney’s plan was pragmatic: dominate as a high schooler, get new game footage, and use it to play overseas—legitimately win where he’d failed before.

  “I think it was like, get to that place that he really feels he deserves. Talking to him, he was like, I don’t deserve to be working in a warehouse in an Amazon fulfillment center. I deserve to be a star.” — Max Marshall (24:57)

• When exposed, Sidney leaned into the media attention, recognizing a value in becoming infamous as a path to fame.

  “He was looking to profit off the story.” — Josh Dean (26:22)

8. Fame versus Infamy: Who Gets to Profit? (26:32–30:43)

• Sidney understood the American appetite for imposter tales and anticipated possible movie deals or at least a platform.

  “There is a cottage industry of stories… There had already been another guy in Texas …” — Max Marshall (26:32)

• The episode confronts the tension between journalists and their subjects: who owns a story and who benefits?

  “You want to use [a story] to your own means. You know, it’s like it’s a natural resource. These stories. And journalists are these prospectors looking for oil. But like, you’re looking for oil in the heart of someone else.” — Max Marshall (29:41)

9. Moral Complexity and the Story’s Dark Thread (31:49–34:19)

• The criminal element — Sidney’s misconduct with a minor — is what makes this tale unfit for feel-good Hollywood fantasies.

  “The whole thing was a much more dark, complicated story than the sort of Hollywood version.” — Max Marshall (32:02)

• Sidney himself is indifferent to whether notoriety is positive or negative, as long as it gets him and his family out.

  “He doesn’t care if it’s fame or infamy that gets him out. He just wants out.” — Max Marshall (33:27)

10. The American Desire for Reinvention (34:19–34:45)

• Sidney’s journey embodies a universal longing: to become the star of our own life movie, to escape circumstances by willpower and audacity.

  “In a way, the whole imposter was he was playing the person he wanted to be. I want to be a star, and I feel like I’m a star, and I’m going to will that into being.” — Max Marshall (34:26)

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Notable Quotes & Memorable Moments

• On the core of the scam:

  “Why would anyone ever want to go back to high school?... You're not looking for someone to pretend to be homeless." — Max Marshall (19:02)

• On media and profiting from infamy:

  “Where I come from, there’s no difference between famous and infamous. It’s all fame.” — Sidney Gilstrap Portly (reported by Max Marshall) (28:49)

• On the lure of the American dream:

  “There’s a huge temptation to see your life as a movie and to see your story as this star cross thing leading to this incredible place with this three act structure.” — Max Marshall (30:50)

• On the criminal line no Hollywood story can cross:

  “It wasn’t just some pure unadulterated hoop dream. It’s this much more complicated, sort of psychological look at the fame that we all want. But ultimately… the relationship with the teenage girl… makes it not something that Netflix is going to want to make…” — Max Marshall (32:02)

• On the ultimate motivation:

  “He doesn’t care if it’s fame or infamy that gets him out. He just wants out. Whatever the route is, if it’s a paycheck that is supporting him and his family. That’s it.” — Max Marshall (33:27)

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Timestamps for Important Segments

• 01:32–02:19: Setting the scene: the arrival of “Rashawn Richardson”
• 03:40–04:15: Coach Harris notes Rashawn’s basketball talent
• 08:51–11:12: Breakout tournament performance in Louisiana
• 12:02–12:24: The season’s peak and its end
• 15:14–16:34: Rashawn's sudden disappearance and rumors
• 16:34–18:03: The unmasking: Rashawn is actually Sidney, age 25
• 18:59–20:59: How the system failed to catch Sidney
• 21:17–23:31: Sidney’s real motives: not nostalgia, but desperation and ambition
• 24:57–26:08: The American dream, hitting reset, and chasing fame
• 28:49–30:43: Who should profit from infamy and who owns the story?
• 32:02–34:19: The moral complexity and darkness at the story’s heart

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Conclusion — The Tone and Takeaway

Chameleon: Big Man on Campus is a nuanced, often somber exploration of the lines between aspiration and fraud, underdog ambition and manipulative deceit. It’s told with empathy for those lost in the system and wary incredulity at a world so obsessed with fame that it becomes both a lure and a trap.
The episode challenges us to question how we incentivize stories of reinvention, and who really wins—and loses—when the American dream is pursued at all costs.

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Outro Note:
The episode closes with one of Sidney’s rap songs (Sin Boo / Real Life Productions), further illustrating his continuing quest for visibility and redemption—whatever its form.

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For listeners:
This summary is designed for those intrigued by con artists, the blurred edges of ambition, and the messy truth behind headlines. Whether you’re hooked on true crime, sports dramas, or tales of American reinvention, this episode delivers a stranger-than-fiction account that raises potent, timely questions.

Transcript

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Campsite Media

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hello. What is.

[Josh Dean]

What do you want me to say?

[Racha Pecorero]

It's just chameleon.

[Max Marshall]

Chameleon Chameleon Weekly.

[Josh Dean]

It's a new term in a new school year at Hillcrest High in North Dallas, and a new kid by the name of Rashawn Richardson has shown up for an early season basketball workout. He's covered in tattoos, wearing a Puma jersey, tall but not that tall, with an average build, and he's unassuming, as you'd expect from a kid in a new place meeting a new group of people for the first time. North Texas is a sports crazy land, and Dallas, its north suburbs in particular, is especially crazy. But Hillcrest, located in a wealthy area where many of the best players go to private schools, isn't exactly a powerhouse program. According to Max Marshall, a journalist who grew up right down the street, the

[Max Marshall]

season hadn't started, and this is a team that took walk ons.

[Josh Dean]

No one knew anything about Rashawn, really, except that he'd just moved from Houston after Hurricane Harvey, one of the worst storms ever to hit Texas, leveled his house and left him homeless. When it landed in the summer of 2017, he'd come to Dallas, where he had family to start over, but he had nothing. No home, no possessions. And because he had no school records to hand over, Rashawn was enrolled as a freshman despite being 17. And this workout with the Panthers, as the team was known, was during one of Rashaun's first lunch breaks at the new school.

[Max Marshall]

He went into the basketball gym and they were sort of having an informal shoot around. The coach was there, Coach Harris, who a lot of people compared to Coach

[Josh Dean]

Carter, as in from the 2005 movie in which Samuel L. Jackson plays Ken Carter, an actual coach who took over his alma mater in Richmond, California, and remade a bunch of tough, undisciplined kids into responsible student athletes. If you listen and learn, you will win basketball games. And gentlemen, winning in here is the key to winning out there. If you believe the movie, he was a good, well meaning man, you know,

[Max Marshall]

very sort of stern but warm. A mentor who doesn't smile much but like, you know, really cares a lot about his players.

[Josh Dean]

Coach Harris watched this new kid, Rashaun, pick up the ball and could just tell by the way he was handling it that he had something special.

[Max Marshall]

He passes him a ball, Rashaun takes it. He's at the sort of corner of the three point arc, shoots, and it's just like such a more pure buttery shot than, you know, you really see in the Hillcrest basketball gym. Passes him another ball, does the same thing. I think he did it three times. And by then a little crowd had

[Josh Dean]

formed watching this kid, this homeless freshman, was clearly talented.

[Max Marshall]

I don't even think then they knew how good he really was.

[Josh Dean]

This is Chameleon, the Weekly, and I'm Josh Dean. This week, the story of a high school hoops phenom who fooled everyone.

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[Max Marshall]

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[Josh Dean]

This is Chameleon Weekly.

[Max Marshall]

Let's get straight to the breaking news. Harvey. Provoking an unfolding flooding disaster in America's fourth largest city, Houston, Texas.

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This is all happening right now as we come on the air, and the situation is unfortunately dire. People trapped.

[Max Marshall]

You know, I think it's still to this day the record rainfall on an American city in American history. And a lot of schools in Houston were closed. A lot of houses in Houston were ruined. And so you basically have a mini refugee crisis in Texas. And right sort of in the eye of all of this, a student shows up to Hillcrest High School and everything he owns from his backpack, school books, but also any form of identification, they've all been destroyed. And basically he is homeless and looking for a place to go to school.

[Josh Dean]

Hillcrest is happy to welcome Rashaun. Schools are, by definition, places to support and nurture children. They exist to be forces for good.

[Max Marshall]

It's not like they immediately sent them to a counselor and said, tell me your whole story. Let's, you know, have a therapy session. I think it was pretty much like, I'm a homeless student. I'm a refugee from a hurricane. I need a place to go to school. And they have protocol for that sort of thing. Part of the story is just how many homeless students pass through the Dallas Independent School District every year. And they often show up with very similar stories and similar lack of paperwork.

[Josh Dean]

So Rashaun is registered as a freshman, and Coach Harris is delighted to have him on the basketball team. The kid just had something.

[Max Marshall]

Rashad had a very specific style of play, which is what a lot of coaches in Dallas told me. They called him a, like a street ball, rec ball type slasher. He's not that tall. He's maybe a little under six feet or maybe around six feet, but he's really strong. He's very low to the ground. Incredible balance. And what he's usually looking to do is to drive to the hoop. He's not necessarily looking to pass the ball and have a lot of sort of ticky, tacky, you know, ball movement. He's looking to run downhill, find a player who's weaker than him, shoulder down, and basically bully ball his way to the basket. For this style of play, he was, especially in a high school context, pretty spectacular. Like you could basically get to the basket at will.

[Josh Dean]

Rashawn wasn't transformative exactly. He didn't turn a Hillcrest team that went 4 and 10 in the 20162017 season into a different team overnight. But he was by a large margin the most talented player on the team.

[Max Marshall]

He had actually gone to another school for a while and then realized the basketball opportunities there weren't going to be what he wanted. So then he transferred to Hillcrest, where,

[Josh Dean]

remember, he didn't know anyone. So for the first few weeks of school, Rashaun rarely took off his Beats headphones. He didn't really talk to anyone and would mostly hang around the periphery at practice, unwilling, it seemed, to assert himself. Coach Harris knew Rashawn could ball, but for whatever reason, he wasn't ready to fully show.

[Max Marshall]

Wasn't actually until the team took a trip to Louisiana for what was called, I think, the Fall Basketball Classic that he decided to sort of fully show what he could do on a basketball court.

[Josh Dean]

These tournaments often pitted the haves against the have nots. Hillcrest was not a have. This was a school that gets invited to tournaments like this so that the big schools with the star laden rosters have some patsies to beat up on.

[Max Marshall]

One of the teams they played was the number one Christian school in the country. Another had a bunch of D1 prospects. These were confidence building games for the other team, I think often. And basically Hillcrest ran what was called the Princeton offense.

[Josh Dean]

This is a tactic used by lesser teams to nullify the strengths of more talented teams. It was popularized decades ago by the Ivy League school of the same name, whose teams were made up of athletic nerds to deploy against major college programs. Basically, in the time before the shot clock, Princeton would pass the ball around well for as long as they could, swallowing up minutes of game time until the defending team just got tired or bored and someone from Princeton would then be open and score. It's a strategy that drives good teams nuts and these days it's played in a modified form. There's still a lot of passing and cutting and screening, but you do have to shoot the ball eventually because of the 45 second shot clock. Hillcrest, Max says, was known to play a version of this and it was not working. At the tournament in Louisiana, the Panthers

[Max Marshall]

were getting smoked and so Coach Harris basically called a timeout and said, you know what new play, get Rashaun the ball. And they would pass in the ball at the top of the key and basically just let him freelance. And sometimes that meant he would do the, you know, the classic LeBron Luka move of getting into the paint and then kicking it out. But often it just meant he was going to play Isolation ball with whoever would take him on, maybe even two on one and just get to the basket and score. And I think in the first game they won. It was a huge upset. And then in the second game, he scored 40 points in three quarters and got written up on some basketball recruitment, Twitter. And the head of the number one Christian school in the country that recruits players basically went up to Rashawn after the game, said, you know, damn, young man, were you trying to go for 70 on me? And gave him a brochure for his school.

[Josh Dean]

Rashawn, having starred on this big stage, blossomed. The shy kid was suddenly the beating heart of the team, and not just on the court. He opened up, started to join late night video game sessions with his teammates, and proved during hip hop sing alongs on the bus that he had some other skills.

[Max Marshall]

Rashawn started showing some guys on the team rap tracks that he had made. And by the time he came back to school in the sort of new year, yeah, he was that classic sort of big man on campus, you know, the sports star that Hillcrest seldom had.

[Josh Dean]

I'd like to tell you that Rashawn turned Hillcrest into a formidable team which suddenly dominated Dallas area hoops, but that's not true. One player can only do so much. Although the Panthers did go 4:1 in the district and beat their arch rival Kimball in dramatic fashion.

[Max Marshall]

Basically, Rashaun's whole career, coaches would always say, you gotta be able to drive both left and right to the basket. And Rashaun would always say, you can't stop me going left. But in this play, he faked left and went right and scored and they won by two. And everyone was like, this is a movie. And I would say that's probably the peak of the season.

[Josh Dean]

But Hillcrest lost in the first round of the playoffs.

[Max Marshall]

Rashaun had fewer than 20 points. So, yeah, I think it was a pretty quiet exit.

[Josh Dean]

Still, he'd made his mark.

[Max Marshall]

Basically, the season ended with him being the district offensive player of the year. And so in the region, he was the guy, at least for scoring. What everyone saw was a guy who had the trajectory and the skills to play college basketball, but also probably needed to hone those skills in terms of passing, in terms of understanding how like a more coached system works, maybe a bit in terms of defense and even in terms of consistency of effort, but definitely a guy who seemed to have the ceiling to play college basketball.

[Josh Dean]

And remember, Rashaun is only a freshman.

[Max Marshall]

I can't remember exactly how eligibility works for a 17 year old. Freshman. But, yeah, definitely, they're planning him for the long haul, no doubt about it.

[Josh Dean]

In other words, there was plenty for Coach Harris and for Rashawn's teammates to look forward to. Then the semester ended, and that was the last time anyone at Hillcrest ever saw Rashawn Richardson Never showed up to school again. What happened? That's after the break.

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[Yvette Gentile]

Sometimes in the quiet corners of our world, or even in the glaring light of day, events unfold that defy the very fabric of reason.

[Racha Pecorero]

There is no scientific, logical, or readily apparent explanation for what we witness. It challenges our understanding, our beliefs, and even our sanity. Why do these things happen? What forces are. Are at play?

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[Racha Pecorero]

And I'm her sister, Racha Pecorero.

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Every week on our podcast, so Supernatural, we dive deep into some of the earth's most bizarre and inexplicable occurrences. We don't just observe them. We actively try to explain the unexplainable.

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[Josh Dean]

Welcome back to Chameleon. When Hillcrest High started up again after the holidays, the basketball team's newest and brightest star, Rashaun Richardson, was nowhere to be found. He simply didn't come back after the break.

[Max Marshall]

All the students kind of were like, what happened to Rashawn?

[Josh Dean]

His absence was obvious, and the rumor mill caught fire.

[Max Marshall]

And I think at this point, there were some. Some rumors about, okay, well, what's this guy's actual backstory? You know, his name was Rashawn Richardson, but his calves, he had a tattoo on one that was S and one was. That was G. And people assumed it was for shooting guard, but at the same time, that didn't really line up with people. I think for a lot of kids, the red flag was the way he took selfies. You know, you're supposed to take them obviously above your head, looking up, because that's the most flattering angle. But he would take them below his nose, looking down like he was reading a book.

[Josh Dean]

In other words, Rashawn took selfies like an old person, or at least not like a Gen Z person.

[Max Marshall]

And then also when they would play Fortnite, his name was Sidney Gilstrap Portly on Fortnite. And then he would say, oh, you know, it's a family member I'm playing on their computer. And then I think the last piece of it is at games. A woman in her 20s showed up carrying a baby a few times and the baby called Rashawn Dad.

[Josh Dean]

So, yeah, I think I could safely reveal now that Rashawn Richardson was not in fact Rashawn Richardson. His real name was Sidney Gilstrap Portly. The name from the Fortnite account was his, as was the laptop. And he was not actually 17. He was a 25 year old with a kid who had already played high school basketball once at North Mesquite High. He graduated in 2011 and even played some college ball at Dallas Christian College. But that's where his hoop career ended the first time. I guess Sidney assumed that no one would notice if he gave himself a do over. But his former high school coach apparently saw one of Sydney's Hillcrest games and contacted the school. That, it seems, is how the story came out. And then one day in early 2018, police showed up at the home that Sidney Gilstrap Portly shared with his girlfriend and their child and arrested him.

[Max Marshall]

He was tucking into some, I think it was Wendy's, he had just showered. Here's a knock on the door, goes to get his gun, thinking, you know, it could be some sort of intruder. His girlfriend alerts him. There's police outside. So he hides the gun under a pillow. And then half a dozen police come in and arrest him, take him to jail.

[Josh Dean]

Which seems a little dramatic, right?

[Max Marshall]

On the face of it. The only illegal thing he did was falsifying government records. And in his mind, he's thinking all this for falsification of government records.

[Josh Dean]

It was actually tampering with public records. But the far bigger problem, Gilstrap Portly, it turned out, had also dated a 14 year old student during that fall semester. The girl told cops that the two did kiss but never had sex. Still, Gilstrap Portly was a 25 year old man courting a 14 year old girl. It's terrible on any level. He was charged with indecency with a child and ultimately pleaded guilty in exchange for five years probation. But that plea came with additional weight. Once his probation ended, Sidney would have to register as a sex offender for 10 years. One of the biggest questions I had for Max was how. How did this grown man just pass for a new teen in school? For starters, he said, put yourself in the shoes of a high school administrator. They are not looking to catch frauds.

[Max Marshall]

A student shows up saying they're homeless. They aren't really looking for liars, especially because, as many people said when I interviewed them for this story, why would anyone ever want to go back to high school? Why would you ever lie so that you could be a high school student? Of course, the imagination can start running pretty quickly for reasons. But I think, yeah, on a common sense level, you're not looking for someone to pretend to be homeless.

[Josh Dean]

So with that in mind, this particular fraud, 21 Jump street by another name, wasn't hard for Sydney to pull off.

[Max Marshall]

A school district is much more concerned about truancy than they are about extra students wanting to take more school.

[Josh Dean]

The most obvious question to me though, is, did Sydney actually look like a 17 year old? Max would know. He met Sydney a few months after the truth came out.

[Max Marshall]

No, he didn't look 17 at all. What everyone said at Hillcrest High School was, including some parents, they said, you would be shocked how grown up a 17 year old can look these days. And some of them attribute it to what's in milk. You see a lot of 17 year olds in the Dallas Independent School District who have tattoos, who lift a lot of weights and so look bigger. Some have beards. A lot are taller than Sydney. And you know, frankly, some of them at other schools are just as good, if not even better at basketball. And so all of that put together, combined with this chaotic sort of underfunded mess of our public school system, I really think it was actually quite easy to slip through.

[Josh Dean]

That's what Hillcrest principal Chris Beyer said. The kid claimed to be homeless. We wanted to help him. Our guards were certainly not up. Also, he said in an interview with a local NBC affiliate, Sidney just seemed to intentionally fade into the wallpaper.

[Max Marshall]

A very quiet, reserved young man, polite. Now, looking back on that now, maybe it makes sense to me that he may was trying to not be noticed or bring attention to himself.

[Josh Dean]

Max Marshall doesn't think Sidney Gilstrap portly created this fake story to go back to high school and date teenagers. That happened undeniably, but that particular transgression was more likely just a crime of opportunity. Max Also doesn't think he did it to be a star, at least not in the way you might think.

[Max Marshall]

When the Dallas Morning News article came out, I think the headline said it was a student looking to relive his glory days. And more than anything, that is what really set Sidney off and made him want to talk to me and tell his story. He felt like it had nothing to do with glory days because there were no glory days the first time around.

[Josh Dean]

This is an important distinction in Max's mind and in Sydney's. He wasn't missing the halcyon days of high school the first time. Those were not great memories.

[Max Marshall]

When I got to Dallas, he was like, okay, well, if you want to understand why I did this, you need to understand where I came from. And so we immediately went to 64 Ferguson, which is an incredibly rough part of Dallas when you Google it. The suggested search result is 64 Ferguson Cripps. And basically, you know, told me his story from childhood, which did involve homelessness, being born to a teenage mother, spending one Christmas living in an unheated garage during a Snowstorm, moving to 64 Ferguson, his dad being in and out of prison for everything from sort of violent crimes, drug crimes. When I finally met big Sidney, Sidney's dad, you know, he told me very openly about the word he used was he was working as a pimp as well. And Sidney, when he was little, his dad would basically have him Transport weed across 64 Ferguson and also other drugs, because who would ever arrest a kid?

[Josh Dean]

In short, Sidney's childhood was rough, as was his adolescence. He was poor, he lived in a very bad neighborhood, and his family situation was unstable at times.

[Max Marshall]

Through all of that, Sidney's sort of idea for how he was going to escape was basketball. He was a really excellent athlete from a young age. And he had the More than a game LeBron James documentary DVD and would basically watch it religiously. He would carry around in his backpack.

[Josh Dean]

More Than a Game is the first of many docs to feature the greatest basketball player since Michael Jordan. It came out in 2008 and follows James and four of his teenage teammates as they show off their incredible skills on the basketball court in hopes of getting recruited to top colleges as a step toward the NBA. James, of course, ultimately skipped the college part entirely.

[Max Marshall]

It was basically the roadmap for him. He saw in LeBron James another kid with an absent father, single mother, food stamp diet, and a real gift for basketball, kind of becoming the chosen one. And his problem was he would go on these teams and he was Very difficult to coach. He would fight with coaches. He would kind of refuse to pass the ball. Kids he considered inferior athletes would play, and he would be benched. And because of his family situation, he was also just moving around a lot. And so he would sort of do well on a team, then start over. But all that's to say is, ultimately, you have a very talented basketball player who played a lot of street basketball, who was kicked off his high school team, who then played, you know, small Division 3 college, couldn't afford that, played semi professional ball, got kicked off that team and was working in a Walmart, working in all sorts of stocking centers, basically thinking, why am I not a famous athlete? And if not that, why am I not a famous rapper? And why do I feel more like my dad than LeBron James?

[Josh Dean]

So that all of that was baked into Sidney's motivation for perpetrating this bizarre fraud. And so what he did was almost pragmatic.

[Max Marshall]

I think it was like, get to that place that he really feels he deserves. Talking to him, he was like, I don't deserve to be working in a warehouse in an Amazon fulfillment center. I deserve to be a star. And one way or another, I was going to get there. I think a lot of us know that feeling. Getting into your 20s, certainly later, you start to feel the distance between that dream and wherever you are in that moment. And I can, in a sense, see the appeal of, like, okay, what if I just turn back and then, like, start that rocket ship off?

[Josh Dean]

Sidney was looking to hit reset on his game box to try to win the game of life High School Edition, on his second attempt.

[Max Marshall]

The reason he gave was, I'm gonna go to play high school basketball. I'm gonna get some tape, show just how good I am, and then I'm gonna use that tape to play overseas and make money. Because basically, he was starting to deal drugs, and he didn't want to make money that way. That's the plan he said he had.

[Josh Dean]

And that plan, well, it failed. One way or another. Sidney recognized that the high school reboot was going sideways. He quit school, and then when the story broke, he didn't shy from it. He leaned into it.

[Max Marshall]

I actually think once I started interviewing him, he was playing maybe even a bit more chess and had to know what a media circus this might ultimately cause, and that's ultimately what he was looking to profit off of.

[Josh Dean]

Max's point, Sidney is savvy. Maybe the basketball experiment failed, but it did get him a spotlight, one that he was very willing to step into.

[Max Marshall]

Sydney understands the media environment like really well. And there is a cottage industry of stories by people like us about imposters. This podcast is part of that beautiful tradition. And even more so, there's even a cottage industry of it's articles about basketball imposters. There had already been another guy in Texas who had two separate ESPN magazine stories written about him.

[Josh Dean]

This would be Jerry Joseph, a 6 foot 5 beast of a forward who led Permian High. Yes, that one. The one from Friday Night Lights into the state playoffs, only to be revealed as a 22 year old naturalized Haitian from Florida.

[Max Marshall]

And then there's that track runner at Princeton who had a big New Yorker piece about them.

[Josh Dean]

As in Alexi Santana, a rangy Montana kid who overcame major personal hardships to win admission to Princeton, land on the Dean's list and become a track star. Until a Yale kid recognized him as a 31 year old named James Hoag, who'd already served nearly a year in prison in Utah for stealing bicycles and who'd previously been caught at age 26 for pretending to be a high school student in Palo Alto. So this is a rich tradition of frauds pretending to be young in order to re enroll in schools. For various reasons, all of them became famous to some degree, which big Sidney. Sidney's dad recognized.

[Max Marshall]

His dad kind of showed up back in the picture and said, Sidney, like, you need to look at what you have in your hands. The world is looking at you right now and you have a story that's valuable. At first I kind of pushed basking and said, I was like, this isn't positive news, Sidney. You know, people are really upset at you. Think of all the sort of hate you're getting. And he basically said, where I come from, there's no difference between famous and infamous. It's all fame. You're here because you think you could make money off my story, and you're here because Sports Illustrated thinks they can make money off my story. And so if y' all can make money off my story, like, who are you to tell me that my story is invaluable? And yeah, I mean, that shut me up really quick. He wasn't wrong. I think Sidney very understandingly started to wonder, why is everyone making money off this story except for me?

[Josh Dean]

When I first reached out to Max about this episode to ask if he'd talk to me about his time covering the story of Sidney Gilstrap Portly, he was a little hesitant. He felt, he told me a little Sydneyed out because he hadn't just written a profile for Sports Illustrated, which came out in 2018. A few years ago, when Campside was asked to co produce a series of short audio documentaries with Meadowlark, our version of 30 for 30, I guess Max was asked to write and host two episodes about Sidney. And when he revisited the story in 2022, this is what Sidney wanted to talk about. The idea of who should profit from his story.

[Max Marshall]

Sidney told me it was like, oh, when ESPN flew down here, what the guy told me is, we're not going to pay you for this, but your story could get turned into a feature film one day and then you will get paid.

[Josh Dean]

This conversation at first knocked Max a little off balance.

[Max Marshall]

And I thought to myself, I've said that to sources before and yeah, it is technically true that someone could get paid for their life rights. But also, you know, journalism is a seduction game. You're coming in and you're acting all friendly and you say you want to hear someone's story, and you do want to hear their story, but you also want to profit off their story. You want to use it to your own means. You know, it's like it's a natural resource. These stories. And journalists are these prospectors looking for oil. But like, you're looking for oil in the heart of someone else. And there is sort of an imposter act. When you come down, you're just like, oh, I'm just like an empathetic listener. I'm just a fly on the wall. I just want to get the story right. Once again, that's all true. But I think Sidney, he saw things in a much clearer, more material light. And I kind of had a fork in the road decision where I was like, do I try to keep up this imposter act of being like, no, no, no, you can make money off this, but I'm just a humble truth telling servant. Or do I say, okay, well, let's talk about it? Because you're right, you're not getting paid for this.

[Josh Dean]

In other words, in the process of telling an imposter story, Max started to feel like an imposter himself.

[Max Marshall]

Sidney and me, we have the same dream for this story, which is what if it gets turned into a movie? And obviously the movie in his mind and the movie in my mind are very different. But we're both sort of doing this Han act on each other where he's selling me on his version of the story. I'm like trying to get my version of the story out of him. And both of us are hoping that we can then turn around and sell that to Hollywood. And that's like, that's what this game is, you know, the through line of all of this is, I think Sidney the whole time is like a lot of Americans, you know, me included. There's a huge temptation to see your life as a movie and to see your story as this star cross thing leading to this incredible place with this three act structure. And the movie wasn't hitting it for him when he was working at Walmart. And I think he was just like, I. Whether this helps me promote my rap mixtape or makes me a famous basketball player, or makes me a famous imposter who gets a movie made out of him, I don't care. I want one of those.

[Josh Dean]

It makes a lot of sense. The problem for Sydney is the criminal part, not the tampering with public records, the relationship with the teenage girl. If it wasn't for that. We're talking about Sidney Gilstrap, portly, very

[Max Marshall]

differently snout to tail as, as they say in Texas. The whole thing was a much more dark, complicated story than the sort of Hollywood version. You know, it wasn't just some pure unadulterated hoop dream. It's this much more complicated, sort of psychological look at the fame that we all want. But ultimately the thing that always keeps it from the green light is the fact that while he was there, he was dating a student. You just think of the psychological damage that it would do on the 14 year old girl to find out that her boyfriend or that the guy she was sort of had a crush on is talking to, you know, late night phone calls, leaving school in the middle of the day to go drive and get chick Fil A or whatever it was, was a 25 year old man with a son. You know, I don't think anyone is insinuating that's why he went to school, but even so, yeah, it casts sort of a thread through the story that makes it not something that Netflix is going to want to make their sort of, you know, know, Thanksgiving movie of the week. And when I said that to Sidney the second time around, he basically was like, well, I don't think that's true. You know, Netflix just made a show about Jeffrey Dahmer.

[Josh Dean]

Sidney's not comparing himself to a serial killer. His point is that all publicity can be good publicity, or at least it can serve a purpose when you are

[Max Marshall]

coming from where Sidney's coming from. He doesn't care if it's fame or infamy that gets him out. He just wants out. Whatever the route is, if it's a paycheck that is supporting him and his family. That's it. If the show turned out to make him into a monster, I think he would still be okay with it as long as it gets made. He wanted to live the dream, I think the Grand Canyon between who Sidney wanted to be and where he was. It was such a vast gulf that the idea of, okay, well, if I'm playing high school basketball, like, I'm the man, I'm the guy. And once that high was over, it's like, okay, well, now I'm the guy who is the high school basketball imposter. What can I do with that? I can go on these YouTube interview shows. I can promote my mixtape. And then when that high dies, it's like, okay, well, what about a movie about this?

[Josh Dean]

As Max pointed out to me, it's a very human story and it's a very American story.

[Max Marshall]

At first he was debasing himself. He was like, oh, I'm homeless. I'm younger than I used to be. I'm a high school student. But in a way, the whole imposter was he was playing the person he wanted to be. I want to be a star, and I feel like I'm a star, and I'm going to will that into being.

[Josh Dean]

And with that, I'll play you out with one of Sidney's songs. He raps under the name Sin Boo, and you can hear more on his YouTube channel, Real Life Productions. That's life with a Y. But you can just type his real name and you'll end up in the right place. Chameleon is a production of Campside Media and Audio Chuck. It's written and hosted by me, Josh Dean, and produced by Joe Barrett. Our associate producer is Emma Simonoff. Sound design and mix by Tiffany Dimac. Theme music by Ewin Leitrimuin and Mark McAdam. Our production manager is Ashley Warren. Campside's executive producers are Vanessa Gregoriadis, Matt Sher, and me, Josh Dean. And finally, if I can ask a few favors before sending you on your way today, please rate, follow and review Chameleon on your favorite podcast platforms to help spread the word. I know everyone says this, but it's true. Ratings and reviews really do help, and if you have any feedback, tips or story ideas, you can email [e-mail] or leave us a message at a special number we've set up. 201-74383, dial +1 from outside North America. Thanks for listening. We'll see you next week.

[Max Marshall]

I think Chuck would approve.

[Casual Conversationalist]

Every case file, interview and archive tells a piece of the truth. I'm Kylie Lowe, and on my podcast Dark down east, original reporting is at the heart of every case I cover. I don't just retell crime stories, I investigate them. I'm speaking with families, searching court records, and piecing together the facts that have been overlooked and forgotten with time. The result? True crime storytelling that digs as deeply into a case as you do. You can listen to Dark down east wherever you get your podcasts.