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Vince Carter was Instagram live and that's my hero pretty much. He saw me like in there. He was
like, Chuck, what's up, man? He was like, we'll drink some Dulce and play golf. And I was like,
yeah, I love that. And in my head, I was like, hey, Dulce, hey, golf. But now I'm just waiting
for the day. Guys, I'm Rachel Lomita and welcome to the Courtside Club. Today, I am super excited
to have my good friend, the official NBA dunk contest coach and CEO of Team Flight Brothers.
You guys might know him as a dunk guru, Chuck Milan. Welcome to the Courtside Club.
Thank you so much for having me.
I was like, are you awake yet?
We are. We're awake, but I don't know like where we're at right now.
There might still be some levels going on in the old blood system right now.
So for those listening and watching right now, we are actually in Cleveland,
the day after the 2022 dunk contest. So this is Chuck's like most wild night. So I actually
appreciate him coming in at 10 a.m. to be on the Courtside Club.
You have to understand like how much I like you as a friend for me to be here at 10 o'clock in
the morning for this. But yeah, it is the morning after. It was fun. Like this is the most fun I've
had like during a dunk contest, even though it was probably like the most misses and like the
worst contest that I've been a part of.
Like just realistically.
Obie and Juan did awesome. Like Juan Toscano.
He was a sleeper.
Nobody knew. And honestly, I didn't even know because I practiced with him in San Francisco two
weeks ago and I was really worried. I was like, why is this guy in the dunk contest? And he was
like, I had to take this opportunity. He worked on everything I told him to work on. So we had
the practice on Thursday night. And all of a sudden he's good. And I was like, dang, man,
like this guy can do good. Obie, we were working with him for a while.
So he had been ready. It's just, he missed a little bit. Like he missed more than I thought.
The dunk over me that he missed, he had never missed that yet.
So I was like super surprised, but.
There's always some jitters and all of those guys who were in it last night are young too.
This is a very big stage for them. Also, I'm from Akron and the Cleveland fans are ruthless.
Yeah. But they were so ready for like when Cole Anthony came out and like started, you know,
playing the crowd.
They were ready because the concert before it was awesome.
I've been a part of, I think, nine all-star weekends and that was the best concert ever.
As I said, that's where all the all-star money went this year.
To that, to that performance. But they had, they had Khaled, Mary J. Blige again. So I was at
Superbowl and saw her again.
You guys are like best friends now. You're like, oh yeah.
Basically, she has no clue who I am.
But she's beautiful and a fantastic performer. My parents were there. They were jamming along.
Yeah. Everything.
I was like this energy. We are so ready. I was nervous about Cole and Jalen
because they didn't practice or like really communicate with me until the night before
the dunk contest.
So can we talk about that a little bit?
I was actually there for, so we went to the Rising Stars game. I met up with Chuck there.
He said, I have practice with, with Jalen Green tonight, day before dunk contest.
The night before.
At 1130, 1130, 1145, the very night before. And we head up to the little practice gym.
And I've been around the dunking scene for a while now, and we can get into that backstory.
We did dunk league together. I followed all the professional dunkers. And when he came in,
he had this bag of all these different dunks. I was a little confused of what's the plan?
Because when you go into a contest like this, I feel like you have to be mentally prepared with a
lot of different things. And you're not going to be able to do a lot of different things.
So you're not going to be able to do a lot of different things.
This dunk, I feel really great. So walk us through kind of like how you felt that night also.
Um, I mean, besides like annoyed, uh, I was just like, it's cause Jalen like looks so
dope when he dunks and stuff like he's really.
He's so athletic.
Super athletic, graceful, like he's a dunker. And I'm just like, man, if we would have done this
four weeks ago and done it two or three times, whole different ball game, like Jalen, like he
probably could have won the thing.
But you can't go into a dunk contest without a game plan. And so like, I'm just like, man, if we
can't go into a dunk contest without a game plan and the NBA contest makes it easier because it's
like, it's four dunks. So all you have to do is practice four dunks. And I just don't understand
why you would want to be a part of something and not be prepared for it. Cause as we saw last night,
like you go out there and there's 20 something thousand people, they're either going to love you
or they're going to hate you.
Yeah. And Cleveland is tough. I didn't realize how tough our fans are.
didn't realize how tough our fans are.
I didn't realize how tough our fans are.
I didn't realize how tough our fans are.
I didn't realize how tough our fans are.
I didn't realize how tough our fans are.
They'll turn quickly. They'll be super amped.
By like the third try for Cole, I was like, are we in Philly right now? Like what is going on?
But I knew it was going to happen. So it was like, it's just like something you have to prepare for.
So the night before, when you were in there, it's like, you were even texting me. You're like,
what the hell's going on right now?
Yeah. But then I was watching him and his forehead is above the rim
in every dunk, whether he's making it or missing it. And so in my mind, this kid is so out there,
like he's already tired. He just played in the rising stars games and he's still dunking with
this much force. All he needs is just to fine tune what these dunks are. And, but I was like, well,
the contest is tomorrow though. So how much time?
It's the NBA dunk contest. Like it is a fun event. So when people watch it, they're like, oh yeah,
this is fun. But as a professional, you have to be like, I got to take this seriously.
Otherwise you'll go out there and you're going to look dumb.
There's a lot of things that go into it. I'm not going to say like, yeah, you,
you need to come to me, but I'm there for a reason. Yeah. And so when you have 15 people
telling you a different dunk to do, and then you have two guys with Chase and I on the side
that we have helped now seven dunk champions in a row, like.
So when were you hired by the NBA to be the official dunk coach?
Uh, I wasn't officially hired until 2018, but I started working dunk contest in 2013
with Terrence Ross. So I was way back.
Terrence Ross, then John Wall. And then it was like Victor Oladipo, Zach Levine, Aaron Gordon.
Uh, and then Glenn Robinson was the one that kind of like the NBA was like,
cause they weren't expecting him to win. It was like if Toscano won last night,
then the Carlton Myers from the NBA, he was like, Hey, like, can we just make you available to the
league? We'd love to bring you on. And realistically, like that's the job I wanted the
whole time, even though it wasn't like an existing job. And so he was like, yeah, like, can you just
be available to everybody? And some people will get ahold of you. Some people won't said, yeah,
absolutely. So now I'm available to everyone. Yeah. And like, my objective is to make sure
everybody's prepared and I want everybody to go in there with the possibility that they can win.
Like, Hey, if you make your dunks, they're going to be fifties. Unless you have the judges from
last night. Uh, they were also really tough judges, Cleveland man, Hall of Famer, Isaiah Thomas. Don't
like you anymore. It's just, oh, that eight that he threw out, Obi Toppin went behind the back over
me and he got an eight and that nobody's ever done that before. But he also, I think another part of
that dunk that makes it even tougher is he didn't push off of you at all. It was a clear jump. Yeah.
Isaiah should know that. Come on. I mean, but I think that's also an issue is that with judges,
like they're so uninformed and they're like old school, like, you know, respect to the legends
and stuff like that. And, and the, the, the, the, the, the, the, the, the, the, the, the, the, I think
they're like, I think they're like, I think they're like, you know, I'm, I'm on the team,
but I don't want to pay tribute anymore. I want to evolve. Like I it's like, yeah, we're here doing
this because of what dr. J did and what Mike did and Dominique and Vince Carter and stuff like that.
But yeah, the game's different now. Like the stuff that guys were doing last night,
if they would have done it in the contest and like 88 or 90, like, there's no way that like
Jordan or Dominique were like dealing with that. I actually, last they were doing more kind of
powerful or or lengthy dogs but it's not as much creativity or art in the air it was literally
windmills pumper versus 360s right and like a free throw line dunk occasionally which is like
wonderful great they didn't have like social media and people just weren't doing stuff like that right
now it is much different yeah and also you know like pro dunking has kind of ruined that a little
bit too because it's ruined it for me a bit well you i mean you saw dunk league like you know it
takes it takes pro dunkers a long time to like make these dumps as well it's just like there's
a lot of editing that goes in so when somebody posts a dunk sometimes yeah there are some guys
that you know that they're ready and stuff but still it's a different thing too because you have
all the downtime right with the nba stuff getting you know the introductions the concerts like all
that stuff no success
stretching and then the crowd yeah you know and you have three attempts so it's like it's i think
some pro dunkers would have i think a lot of pro dunkers would have trouble in that situation as
well i want to get back to judging and and just contests in general because i feel like we could
go deep into that conversation but before i want to let people get to know you a little bit better
you started we met what 2013 yeah something possibly yeah
so if you guys don't know before i was on 2k before i was doing a lot of the hosting stuff that i'm doing
now i was on youtube just collaborating with any different channels and people that i could
and something that was big around that time was the professional dunk scene was really coming up
yeah so i would hang out with you guys uh jordan kilgannon who's like one of the the biggest
dunkers in the world right now i'm possibly the number one dunker i mean the most popular dunker
in the world for sure most popular for sure and i kind of early saw this scene of these
guys and i was like oh my god i'm gonna dunk them i'm gonna dunk them i'm gonna dunk them i'm gonna dunk them
guys who were super athletic they didn't hoop they didn't play five on five but they were
professional dunkers and it was before it was even really popular you had already been in the game
well before we even met so how did that start for you uh so i played in high school and then i played
i played a little bit in college i was in a dunk contest one summer and it was a miami a hoop it up
dunk contest yeah and i went to miami people didn't know me there like in my hometown everybody
could jump whatever so i went to miami and i'm the only white guy there whatever uh and so they
called my name during the dunk contest and everybody was like ah yeah like what's this
little white guy doing yeah let's see and so i ended up winning the dunk contest and the place
like was going crazy and a representative from nike came up to me and he was like hey there's
a brand activation we're having in asia for jermaine o'neill's like new shoe they're like
we want to bring an american and at that point there was no like professional dunkers like that
wasn't a thing in america like i didn't even know that there was a brand activation in america
was like guys dunking into france uh-huh they were like when you come here we'll give you
thirty thousand dollars for the you know for like a month and a half over here and i'm 18
you're like what so i was like i was like yo i'm out of here and so i i left and i started doing
that and then when i came back i would do like in one stuff like i would play on the opposite team
i was like man i have guys in my neighborhood that can dunk better than i can and it was true
it was a dunk contest for like twenty five thousand dollars and like two or three days
before it happened i broke my ankle oh geez so i was like man this sucks you know what i'm gonna
have one of my i'm gonna be like yo i have a replacement though it's one of my friends i sent
my friend and he ended up winning the thing oh so so i was like man like i have another friend
they had like another event i was like i have two other friends said those and they started like
doing stuff and these are just kids and they're like oh my god i'm gonna be like oh my god i'm
gonna be like oh my god i'm gonna be like oh my god i'm gonna be like oh my god i'm gonna be like
it's and that you got that yeah that i grew up with oh crazy and so then it was like man like
we just started this whole flight brothers thing and it was like oh team flight brothers and so
i started uploading videos onto like streaming services that you know it was like dial up at
the time right this is before youtube people were like downloading our videos on like kaza
and limewire and stuff like oh my gosh do you remember yeah so like they were downloading
like dunk videos on there and then youtube
came out and i was like hold on i can put stuff up here for free yeah awesome so i started doing
that and we put a video up of a of a five nine dude t-dub ended up on the front page and this
is like 2006. and if you're on the front page of youtube in 2006 it's like 2 million views over now
oh absolutely we're not getting paid at that time but it's whatever youtube wasn't as saturated so
any video that had that was dramatic
in any sense whether it was like somebody falling down the stairs if it was cats doing weird things
a squirrel looking at you you know like anything funny if it was charlie the unicorn do you remember
that one oh of course yeah it was like og youtube days oh my gosh charlie the unicorn um but yeah so
we put that video up and then a couple days later a representative from youtube hit me up and was
like hey we're doing this event in new york city it's called adsense it's kind of like on the low
end of the road you know like you're going to go into a club so we put on a dunk show while a
soldier boy played oh my gosh yeah he was playing crank that i because he it had just come out so we
dunked during that and it was like us like esme denters like it was like the weirdest so i was
probably junior senior year of high school yeah that's what's happening for sure and so that
happened and then they were like hey we're starting this partner program where you can get paid so
we're doing this awesome thing and then in a month or two months later it comes and i'm not even
thinking about it and i'm coming home from work i this was at a hotel i was like just working front
desk at a hotel and i like go and see my bank statement and it was like 18 000 in there and i
was like immediately called one of my dunkers i said hey um like pack your stuff move into florida
yeah moving back home and i literally like moved back home and that was the last time i had like a
regular job and that was like that's awesome
That was like 23 or something like that.
But yeah, that's like how everything started rolling.
And then people started booking us for shows just from seeing us on YouTube and stuff like
Well, I think a lot of people don't know the grind that goes into it before you're in this
And I talked about it on a previous episode.
People sometimes know of you or you're famous before you're actually making real money.
Because it takes a while for that to build up.
And even when I first moved to LA, I was working in a restaurant and doing these commercial
and modeling jobs on the side, just trying to make ends meet because as a full-time creator
host, that wasn't in the cards.
It's like real stuff.
There was literally a time when I moved to Massachusetts, my ex lived with her parents
and I couldn't live with her parents.
So I legit lived in my car for like four weeks and all I was doing is working and putting
half of my money towards flying dunkers in and filming them.
I'd put them in a hotel and I'd be like, yeah, I'll come get you in the morning.
And I was sleeping in my car.
So it's like, people don't understand like what happens before.
Well, that's also a testament of how much you loved the dunk game and how dedicated
you were to growing it.
And then to see where you're at now, I feel like that's, that's pretty cool.
You should definitely be proud of that.
I mean, it's super dope.
Like even last night, the dunk contest was, you know, whatever, but I never appreciate
the moment like with the NBA dunk contest while it's happening because I'm so worried
about what everybody's going to think.
It's so interesting on social media because we're so, it's so easy to communicate with
us on social media.
Because we see it.
We don't pay attention to it, but we see it.
And last night was the first time I was like, man, you know, when you think about, man,
those were good times before.
I was like, you know what?
This is good times right now.
So now I'm just trying to enjoy everything as it happens.
And you were on the court for Obie's first dunk.
If you guys watched it on TV or you were at the dunk contest, that's who Obie jumped over.
Can you say, can you.
Can you tell everybody your height too?
Because you look short up against NBA guys, but you're not.
Take, don't take this the wrong way.
My agent was, I was like, oh, that's my friend Chuck.
He was like, oh, well that's good.
He's dunking over him.
Cause, cause he's like five, six.
I'm like, he's not five, six.
It's just in literally, I think I told you that like one of my friends, she was like,
Hey, she was like, my friend thought you were cute, but it was like, man, he's like five,
And she's like, he's like, he's, she was like.
He's like six, one, like six foot.
I was like, yeah, I just stand next to seven footers all the time.
So that's like, that's what happens to me.
So I have to like crop people out of my Bumble pictures and stuff.
Or you need to just put a little like ruler or whatever it's called next to you just to
show how tall you actually are.
So before we go more into the dunk game, I want to take a halftime break.
If you're down with that.
Yeah, we can do this.
Since you, to me are like a dunk encyclopedia, your knowledge of.
I have some dunk trivia for you.
I don't want to see how well you do.
We'll start off with a couple of softballs in 2008, Dwight Howard pulled out a heroic
dunk for a second attempt of the night.
What superhero did he emulate?
I mean, even I knew that one.
Did you, have you worked with Dwight?
I worked with him in 2020.
I started to, we actually had a dunk planned out that Kobe was going to help with.
So we had a dunk where you throw like a lob to him from like underneath them.
Kobe would be sitting in a chair, whatever.
But we were like, we don't know if he's going to do this.
He was like, what do you want me to do?
It was like, yeah, just a pass to Dwight.
Like you sit in a chair.
He was like, early January then?
Uh, this is literally four days before it happened.
So I was supposed to fly to LA and work with Dwight and Kobe.
And then that happened.
So that was like the wild thing, but I like talked to him on the phone,
like four days before it happened.
Never had any interaction.
He was like, and also heartbreaking though.
And that kind of like Dwight didn't really practice after that.
He was crushed when that happened.
People that have a lot of things to say about Dwight and Kobe, but they actually
were pretty close, like after all that stuff, right.
And that would have been iconic too, to kind of solidify that.
But I can't even imagine if you have that planned as one of your dunks.
And then pretty, yeah, pretty, the whole world cried.
I mean, it's still, it's that moment in here.
It's that moment in our generation's history.
It's our, like, you know, our JFK like type deal.
Well, moving on to, um, something actually, actually about Kobe Bryant.
We'll honor him for a second.
Vince Carter and Kobe won every competition that occurred in the
four years between 1997 and 2000.
But how many contests did each of them win during that time?
There was no contest lockout and no contest because they brought
two ball in and broke my heart.
I was like, that was a trick question.
But that was so easy for you also.
And Vince won in 2000.
And God rest his soul, but Darvin Ham should have won.
In the 2005 competition, Steve Nash showed off his soccer skills, passed an alley-oop
to which, Amari, where's Stoudemire.
So is this like the easiest dunk trivia you've ever had?
Um, I mean, yeah.
That's a tougher one to have.
Who won the 1985 dunk contest?
Uh, Dominique Wilkins.
Ask me the lineup if you want.
I mean, I'm, I'm just, I mean, so the other morning, Chase, my assistant, we're
like just walking into the tunnel and he was like, tell me you ever got those in
the 84 contest and I like spit it out immediately, immediately, like the first
name I said, he was like, yeah, this guy knows.
So that's something.
That you, do you study these to prepare the guys as well?
Like I, I study, like I watched dunk contest all the time.
Like real life, we all deal with like, you know, like some sort of like mental health
things and stuff like that.
And I dealt with like depression growing up and a dunk contest with like, it was
just made me feel like, okay.
So that was always my safe Haven.
So I had like tapes and like all these contests recorded.
So I, it's like my safe place.
So by doing that, I'm like, oh man, I know every dunk that's ever happened.
And cause I've watched it, you know, like the 10,000 hours, things like definitely
How many players have won more than one NBA dunk contest?
So we got extra credit if you can name them.
Uh, Dominique, Michael Jordan.
Jason Richardson.
Oh, you said two.
Oh, more than one.
No, you're right.
Uh, and then who was in Zach Levine?
Did this is Obie's first.
He was in it last year.
He was in it last year, but he didn't win.
Maybe he'll add, maybe if he.
I, last night, his agent, who's one of my best friends.
It was like, he's done.
He's not doing it.
And I said, listen, he's like, it makes no sense.
We'll probably be in the league next year.
So we lobbied and I'm like brother versus brother in a dunk contest would be so dope.
And he's like, okay, you're making sense.
We'll get back to it.
We'll check back in with them in January.
And Obie wants to do it.
Obie's like, yeah, man, let's go.
In 2007, the five judges who are all past champions of the NBA slam dunk contest.
So we have multiple choice.
What past dunk contest winner was not one of these judges in 2007?
We have Michael Jordan, Vince Carter, Jason Richardson, or Kobe Bryant.
I think it was Vegas.
Michael Jordan, Vince Carter, Jason Richardson, or Kobe Bryant.
Jason Richardson.
Wait, one more question.
Who did the 2022 dunk contest champion, Obie Toppin, jump over for his first dunk in the
That would be me.
The Chuck Millock.
Time for the second half.
Where's my trophy?
You didn't bring it.
Dude, that thing is heavy.
So we talked about it last night.
He said, listen, if I can get the dunk contest trophy, I'm going to bring it to the dunk
Obie was having a lot of fun with that thing.
But I have a whole Snapchat with it.
And I'm just like, I think it might be on my story.
And it's just like, I ain't worried about nothing.
I'm like carrying the thing.
It's kind of like a glass container this time.
Or crystal, something.
I like the old school stuff.
But it's super heavy.
It's probably like 25 pounds.
He handed it to me with one hand.
I mean, it's nice.
But you don't even know what it is.
You really have to look into it.
Because it's like slam dunk champion and like a weird thing.
But bring back the old one.
Notes to the NBA.
We need a different trophy next year.
Speaking of contests, I noticed that the scoring and dunking, it's never consistent.
And personally, I think it needs some work.
There needs to be some sort of revamp.
Because I see these guys.
And especially when I see these guys, I'm like, oh.
what is what is your take what do you think needs to happen for for scoring yeah so with the nba
dunk contest what happens with the nba even though like they changed so many rules this year with
like rookie game and all that stuff which was like fun or whatever thanks for the seat uh you got it
but they don't want to over complicate things right you know because that's not what they like
work for that's it's more of a show it's a show yeah so the dunk contest will not do anything
besides like next year we're gonna add decimals so there's no like ties and stuff oh cool yeah so
that's like and then maybe have the judges a little more informed we may be taking the dunk
school with me for like 30 minutes now for pro dunking there needs to be a system uh i know
there's like a couple like different people that are trying to make systems and stuff like i'm
obviously trying to do that as well but it's one of these things that's going to have to break down
like a category of like figure skating type of thing yeah where it's like originality
and like are you nailing it on the first attempt right how clean is the dunk type of deal and it's
going to have to be like a culmination score the ultimate objective objective with pro dunking
is to get into the olympics like that's my that's my like last thing like you know like
when dr dre was like you know f rap after this you can have it back yeah like that's how i feel
about dunking have you watched gymnastics of course at all yeah do you know how they score
uh yeah so they had to change it because it used to just be just up to 10. perfect 10 whatever
but now in the olympics that when you when you see people start excelling now you have a routine you
have a certain number of skills that you're doing in that routine and they give you a difficulty
score so put a difficulty on these different levels of dunks right yeah if it's something
we've never seen before that's a whole another level of difficulty or that adds up another
decimal another this another that yeah if it's my clean dunk you know you get
one or two decimals off there that's how i've envisioned it because even on dunk league the
show that we were on i've i saw the guys some of their disappointment and some of their even
somebody who won being like i i shouldn't have won this challenge it should have been isaiah yeah
you know it should have been i think it should have been it should have been somebody else and
like you said the nba guys are doing it for entertainment they're making hundreds of millions
of dollars in a year that's a lot of money and they're doing it for entertainment that's not
the same thing that you have for a lot of people so if you've got a lot of people doing it for
entertainment you're doing it for entertainment but you're not doing it for anything you're doing
it for a lot of people it's just it's a it's a different kind of thing and i i think this is
the one thing that is really important and it's a really important thing to keep in mind is that
when you're doing a dunk contest you're not just doing it for a show of dunk it's a great show for
the crowd it's not life-changing for them to win twenty thousand dollars then to win ten thousand
like the scoring needs to needs to be fixed and gotta start taking stuff seriously because i've
been doing so many things that right i took myself away from pro dunking like putting myself 100
into pro dunking uh and now it feels like if i'm not like pushing the needle like nothing's
happening like it's the realization that like i need to do it that's what's going on next
is that i'm just gonna throw myself back in a hundred percent and just but i think at the same
time what you're doing with the nba is really important because this as it stands right now
this is still the biggest stage yeah so we need the big and i i just threw myself in we because
but we need that that big stage to keep people interested in it and if there's a way to even
get some of the pro guys i know i keep talking about this for those of you who are watching or
live watching this and you're watching this and you're watching this and you're watching this and
you're watching this and you're watching this and you're watching this and you're watching this and
listening who haven't checked out some of the professional dunkers i mean if you want to
rattle off some of your guys so they can check them out on social media they've done dunks that
if you were impressed by any of the nba dunk contests your mind will be blown once you see
these guys dunk because it's that next level shout out to the nba guys who are great but
but these guys are even on it it's just like they they devote their lives to dunking as
an nba player devotes their lives to basketball yeah um like like jonathan clark and
jordan kilgannon and dan gross jordan sutherland even chris staples like those kind of guys like
devoted their their selves to it uh can we talk about uh jonathan clark one of our good friends
we've all collaborated multiple times most wonderful human on the planet he's just wonderful
is also a high school high school teacher teacher yeah and he does a standing backflip into a
vertical dunk yeah and has done what is he working on now double between the legs he's he's
the only person that hit a double between the legs so far and then he like he was dunking for a
full year with a torn mcl and we didn't know and then he went and got it fixed and so now he's like
making his he's getting older you know like he's 34 years old and he's like putting his everything
into he's like man something's gonna happen and i'm making one last push because i know
my legs aren't gonna keep going right which like breaks my heart because i want guys like that
to reap the benefits of like what they built like i have
guys that i would you know had with me in 2005 that they see everything going on and people are
making pretty good money now and it's like it breaks my heart because i remember us like
jamming into hotel rooms and you know doing dunk shows for 200 and stuff like that right so yeah
i remember telling guys like like chris staples and jordan kilgannon and you know shoot i mean
whoever there was like porter mayberry back then and stuff i was like hey like you i'm i'm gonna
help you no matter what like
i'm gonna get you events and i'm gonna do this stuff but you need to start building your own
brand because there's gonna be it's that thing there's life after this you know what i mean and
that's you know jordan i see him doing a little more like like some ad work and some like some
brand stuff which is like great because even though he seems like superman and i mean the
dude's in incredible shape same thing like yeah those legs don't last forever definitely
courtside club is presented for the people by caesar sportsbook the greatest sports betting
app of all time download it must be 21 or older has there been one nba player or nba legend who's
talked to you or kind of give you praise that really i don't know if that sticks out for you
um when we uh well the last time when we were in atlanta for the kellogg's game uh dominique
wilkins like he was like he was like he was like he was like he was like he was like he was like
i was in a elevator with with shaq and dominique and then shaq like said something he was like you
know who that is and he was like i know who that is man he was like that's the dunk he was like
that's the dunk god right there i was like dominique wilkins called me the dunk god and then uh i was
during covid i was uh i did like vince carter was instagram living all the time and that's my hero
pretty much and he was like oh he saw me like in there he was like chuck what's up man he was like
he like jumped on the live and he was like telling people he's like you know this is the goat right
here people call me the goat but this is the goat and i was like vince carter's calling me the goat
right now that's so cool and i'm like trying to screen record him yeah didn't get it but i was
like man did you even know that he knew who you were no that's cool i had no idea that's so cool
yeah i was like the i was just like man and i remember i like called my brother i was like
vince carter just called me the dunk goat or whatever and that's so cool now i'm supposed
to play golf with him and i lied to him and told him i was good at it i'm in trouble oh my god
how long do you have before you're gonna play golf with him no actually no actually i'm getting
kind of good now because this was during covid he was like yeah man i gotta make it down to naples
there's a course down there i'm trying to play man if he sees this my bad man it was just he was
like well he's like we'll have some dulce and play some golf i was like what are you supposed
to say if vince carter asked you to play golf you're like obviously immediately i was like yeah
i'll you know i'll kill you i've been practicing like six hours a day before the game i literally
it was just so funny because he's it was the same live and he was like yeah he was like
we'll drink some dulce and do the and play golf and i was like yeah i love that and in my head
i was like hey don't say hey but now i'm like now i'm playing and stuff i'm just waiting for the day
that's so cool for me it was a similar thing when kobe when i was interviewing him and then
after he was like i've seen your shot on social media like you have a great shot keep going how
have you seen me you know for kobe bryant to compliment my three-pointer which just
insane so you have little moments like that that kind of take you back like wow the life that we're
living is really cool and the fact that we're able to be in this circle is yeah it's an experience
that the people would only dream of and the word you use is like desensitized and it like sucks to
like once you say it you're like man what are you saying right now but it really it's become a thing
but everybody's so cool people make this uh assumption that athletes or celebrities are you
know rude or whatever
yeah and it's like you rarely run into somebody that's like true that's like that so it's like
they're they're the same as we are except for you know in my case they're usually kids they're
younger i feel like especially in the basketball space too like the athlete community is a lot
warmer and at the elite basketball level it's kind of a small circle you kind of see the same
people we all know of each other there's a level of influencers and social media people and then
the television folks and then the actual athletes yeah the pro dunkers and kind of everybody in the
between yeah but we're all connected in some way it's like it's like a weird like brother sisterhood
thing definitely but it's dope there's a level of respect to it yeah all right so we are nearing the
end of the game and i have some buzzer beaters for you before we go what is the best game that you've
ever been courtside for i guess you could also say con dunk contest because you've been courtside for
a lot of years it doesn't have to be an actual game i'm just gonna go dunk contest um you would
think i would say like the ones i would say i would say like them but like actually they're just for the
I was a part. Derek Jones jumped over me when he won and then Obi last night. But in 2017 in New
Orleans, Glenn Robinson was not supposed to win the dunk contest. I remember that. And he was a
15, 14 to one to win in Vegas. So obviously I threw money on because I was like, we're going
to win. Yeah. And nobody knew that I was working with him. Everything played out the way we thought
it would. We had him do like his best dunk first. So everybody else would try crazy stuff. It's
exactly what happened. That's smart. And it was the coolest moment. It was my first like assuring
moment that I was like, okay, I'm supposed to be here. Yeah. So I would say that because I wasn't
on the court, but I was like right with all the players and I just like watched it unfold and it
was just so cool. And then he gave me his trophy. So, oh, so cool. You said you did the toughest
dunk first. Is that, that's not normally the strategy though, right? No. Okay. No, because I
thought everybody like usually does something safe,
but tries to get like a, you know, 45 to like 48 out of 50. Right. And I just told him, I said,
Hey man, I said, this is your best dunk and you can make it every time. Let's do it first. And
because nobody expects it from you. Right. And literally nobody expected it. And everybody's
like, what just happened? He got a 50 and then everybody changed their dunks. Like Derek was in
the contest. Uh, and he even told me, he was like, when he did that, I changed my dunk.
I was like, so it got in his head a little bit. Yeah.
Same thing. Aaron, Aaron brought his drone out and he wasn't supposed to do that until like the
finals. So he like did the same thing. And he was like really trying to avenge like the previous
years. So I'm two and all against him. Sorry, Aaron. Also a nice guy, but all right. If you
could say courtside with one person dead or alive, who would it be? Yeah. Kobe. Kobe. A hundred
percent Kobe. Just, just to hear like him talk about the game, like him dissect it and stuff.
Right. That would be, yeah. Who is one guy that you would love to see poster somebody
while sitting courtside? Like right now or just any, anyone in history?
Nate Robinson on Shaq. Oh my gosh. That would be so good. Actually, that would be good for today.
I don't know if like either of them would ever be on the court together ever again. Totally. What is
your ideal food and drink combination while sitting courtside? What? Okay. Wait, what drink did you have?
Last night that you would have right now? If you were courtside, what drink didn't I have last night?
No, I like a tequila water person. Tequila water. Yeah. What? It's light on the calories. I'm trying
to get a scholarship. That sounds gross. Sorry. I need tequila with all of the mixing things to
make it taste delicious. Just some wine? No. Expand your horizons, kid. Gross. So basically
just melt the ice cubes in the tequila. I'll have it sent to you.
Okay. And last question. What is one event in history that you would have loved to have been
courtside for? It could be sporting event or other. 2000 NBA slam dunk contest, Vince Carter's.
That was my 16th birthday. Greatest moment of my life. I literally do not celebrate my birthday
anymore. I'm just like, oh, Vince Carter won the dunk contest on this day. All right. Well,
when you guys go to play golf, you got to let me know when that date is. We'll hire a camera crew
for you so you can document every single part of it. A hundred percent. I will. And then you should
go on your birthday. That would be awesome. All right, Chuck. Thank you so much for joining us on
the courtside club. Before I let you go, let everybody know where they can find you and
anything that you have coming up that we should look out for. Well, you can find me later at Top
Golf. On Instagram, my business account is Team Flight Brothers. And then my personal account is
TFB Chuck the Boss. And then on Twitter, it's TFB Chuck the Boss. If you want to know how I'm really
feeling, just go ahead and follow me on there. Oh, yeah. He lets us know.
All the smoke. Yeah. Well, yeah, that's where you can find me. Dude, thank you so much. Thanks for
waking up and joining me. It's been a really fun weekend in my hometown. I appreciate you.
Appreciate you. Thank you. Thank you. All right, you guys, make sure that you subscribe
and like, and there's more courtside club coming very soon. Bye.