Many people have been wondering what happened to Anthony Pappalardo. He seemed to have it all, and then, one day, just disappeared off the face of the earth. Was he on drugs, lazy, unmotivated, have a serious injury? Unfortunately, any of those possibilities would have been a lot better than the situation that Pops found himself in. It’s a dark story. And there are some valuable lessons to be learned from it. Four months ago I contacted Anthony with the hopes of getting him to tell it. The result is the honest and introspective narrative below.

48 Blocks: Let’s start with Converse, what happened with your shoe deal?

Anthony: I’ve always kind of hated bitter-type interviews. The last thing I ever wanted to do after reading / hearing somebody talk shit is go out and skate. Talking shit is easy. It will always be. Go learn how to ride a skateboard. That is hard.

Every time I sat down to answer this question, I found myself  avoiding it, fabricating it, or blatantly lying about it. I would tell myself that I’d try again tomorrow. I realized that if I was going to answer this truthfully, there wasn’t a chance in hell to keep it positive. That sucks. The driving force behind anything that I’ve been asked to be part of, from video parts, to an interview, etc is in the hopes that it inspires people enough to want to go out and skate. That’s it. And if by chance, that scenario was ever the case, nothing makes me more psyched.

For anybody that has ever been into what I do on a skateboard, I feel like I owe them the truth. For the past 15 years, I worked too hard for  people to believe I burnt out in some bullshit flame built out of speculation, lies, assumptions, etc. I’m the first one to realize why these things get created, and even exist in the first place. I have always dealt with it throughout my career on some level. It’s pretty logical, it’s  just the outcome and what gets created if nobody gets the truth, or anything for that matter. As of today, looking back throughout it all, I probably have more fingers on one hand than I can count in my whole career (or life) that I’ve been lucky enough to experience—these things made me proud, honored, and maybe even feel a sense of achievement from skateboarding. Since the last one of these things, and coincidentally the most recent, directly relates to your question; I’ll bore you with the others as I would like to thank each and every person that was ever a part in making these possible.

  • Coming home from school and listening to a message on my answering machine from Rob Dyrdek.
  • When I went “officially” went amateur for Alien Workshop, and Joe Castrucci made this little commercial for it.
  • Walking and skating—I still remember the exact street—and talking on the phone to Rick Howard about riding for Chocolate. And getting a text from Aaron Meza about a month later telling me to look at Crailtap—my Hecox portrait was up.
  • My Lakai video part. 
  • And lastly, being in a  bar / restaurant surrounded by friends, family, pros, and people that I’ve looked up to for my whole life growing up, respected beyond imagination, all gathered there because my name was going to be on the back of a Converse shoe. The craziest part of that,was that they were actually all accepting that fact, not talking shit on the idea of it. It fit, and people were congratulating me. It was really the natural progression of things. People were stoked on it. And just maybe, I deserved it. That will be coming up on three years ago. 

This is what I know about myself and that company. It’s a company that I  risked my whole career on. That I quit another shoe company that I  had a previous good relationship with and was loyal too for over a decade to ride for. I was asked one month after I just put out a video part which just happened to turn out to be in the biggest, most watched, skate video of our decade. And, at that time, to take that risk was nothing more and still was just an idea. There was nothing concrete, no shoe designs, no team. They were having a hard time getting one together for pretty obvious reasons. Most people  don’t  like risking good, stable things in their life that they invested and worked their ass off for to ride a non-existent company with  a history of  failing in the skateboard world at least  two to three times already. It wasn’t like they were offering “free life” contracts. That’s for sure.

After going back and forth, I ended up getting them to at least match what I was getting from Lakai at that time. It was sketchy. And it was a major risk. But I took it. I had to stick to my guns. I had to believe it could work. But I knew it could work if done in a specific way. And they were on the same page as I was about how to make that happen. With the Lakai video being released at that time, I was just what they needed. And they got it. No big deal, that’s business.

The first two years that I rode for them was completely mellow. It felt like any other sponsor that I’ve ever had. This would be around the time there was some talk of releasing my shoe. Things were looking good. This company was actually starting to work. The brand was finally showing some stability. It seemed like everyone, all of sudden, wanted to ride for it. I gave my input, helped, and backed who I thought would help make this thing work. I wanted nothing but the best for this company, like anything I’m a part of. I take a lot of pride in who I ride for. I only ride for companies that I think are the best out there. That’s the only way it’s ever going to be for me. 

At about that same two-year mark in, Converse starts giving me a little shit about getting some coverage. They had every right to. They just dumped all this money into the release and promotion of my shoe. I had just put out that Epicly Later’d, and it seemed to be getting some  pretty good feedback. Around the same time, Meza flew out here for a weekend and we filmed that Red commercial. I mean things seemed to be pretty much on the same track that I’ve been riding on for the past 12 years, if not better.

I felt like people were starting to get my Lakai part. I remember almost out of nowhere, kids were coming up to me just being so psyched, positive, and supportive. It felt good. It was also contract time again with Converse. All the original guys needed to renegotiate. And they were trying to integrate all the new guys into the program. This is pretty ironic. If I was forced to pick a time that I actually felt semi-confident about how things were working out career-wise, those couple of months would have been it. This company was about to release the first run of my shoe, and threw me this party celebrating it a couple weeks prior. I wasn’t being some asshole on a deserted island somewhere sipping Mai Tais. I stopped drinking over 5 years ago.

Literally, out of nowhere and for absolutely no reason, they started getting real shady with me. I seriously couldn’t understand why. Word was, my shoe was actually doing all right. Actually, I don’t know that for sure. To this day, I have never been told. But it seemed like every single kid in New York was running them. They were everywhere. Since they kept it running the following three years with a total of over twenty different colorways being released, some as recently as four or five months ago, would I be the crazy one to say it was probably a success? Especially considering that after the first run, they totally stopped supporting the shoe and myself. I was essentially being held hostage, just being told, “There wasn’t one person out there who might of actually bought it, or supported it because of the lifetime of work that I put into skateboarding. So I just had to get over the fact that my name was on it. And that there wasn’t a shop out there willing to touch or support a thing with my name on it anymore.” I look back and see how psychologically that did fuck me up. I was believing that.

I would go out skating at that time and get nothing but tons of positive feedback running into kids all day everyday. But I didn’t believe it. It’s almost three years later, and honestly, I think I still get more kids coming up to me now than I ever did during any other time in my career. And I still have a hard time with it. I would literally love to know what I ever did to that company except help it.

Six months ago, I walked into the huge converse store on Broadway in New York. Two skater kids who looked like they were on vacation with their folks were looking at, and eventually ended up buying, the shoe with my name on it. I watched from halfway across the store, and instantly had to break out. I was just so bummed. One of the kids had a Chocolate shirt on. If I had a dime in my pocket that day, I would bet any person at Cons that if I would of went up to those kids; they would of knew who I was. That was two years after I was told that there wasn’t a shop or kid left who would support anything I was a part of. This is how it more or less spiraled out control, or more or less their way of justifying that they just exploited me to a pulp and were about to do things you sometimes hear about, but never really believed unless you’re some hippy living in a shack in Costa Rica.

You didn’t think human beings were really capable of acting out such corrupt shit. To this group of people that I was riding for, and about to renegotiate this new contract with, only what I did during those two years mattered. I was being told it wasn’t up to their standards—which at that time is complete bullshit. I was doing stuff pretty regularly during that time. After is a different story, which I take responsibility for. But everything I was being called out on was  just so damn hypocritical. The only reason I ever got the fucking chance, and ended up riding for them in the first place was literally because of a video part I put out a month before I ever signed their contract. So they get to pick and choose what I’ve done in my career at certain moments. It doesn’t work like that. It has never worked liked that. It’s a pretty easy concept. When you decide to sponsor somebody, you obviously get the person’s baggage and history,

I kind of blacked out the phone call where we had to renegotiate. A lot of things were just so ridiculous. I remember him saying, “You know Anthony, the guys that ride for Cons are all A-list pro status. That’s our brand, you know? And honestly you’re just kind of a C-grade pro.” I’ve never been so insulted in my entire life. I couldn’t fucking believe they had the nerve to say that. I seriously remember it just getting real quiet, so silent, and just having a million thoughts running through my head. I couldn’t even say one of them. These were the same people I looked into the eyes of at this party they threw for me a month prior. It was just so fucking disgusting.

I actually hung up with a goodbye at the end. It was officially left at me not being at the level of being sponsored. Therefore, no contract anymore, no deal. Literally, I wasn’t sponsored anymore by them. The icing on the cake was I found out the day before that the other team I rode for, Elwood, was going to stop paying their skate team. So it was a wrap. Just like that, in a literal snap of their fingers, they decided to take my career into their own hands, and prematurely end it. Everybody on the team got resigned or added, except myself.

People don’t realize this—and I don’t really know how not—if you’re not 15 living in your parents house anymore, when people stop paying you to ride a skateboard, that’s it. You can’t put the time and effort in to worry about trying to film some trick. All of that goes out the window. Within 24 hours of that call, I was literally stressing about how I was gonna eat that night. I was living on nothing but purely survival instincts. And the most frustrating part of it is nobody knew that. I was living this double life. It was a lie in the sense that I’m out there still trying to live up to those expectations of being a pro skater. But it wasn’t  possible. Believe me, I tried. I really fucking tried. And that was just basically the hell of what has been the past two-and-a-half years of my life. And this is the sketchy way they were able to get away with doing that to me—a couple hours later that night, I get a text:  ”Anthony, I really feel bad for how this worked out. So I’m able to offer you this as a contract for the next two years.” It was fucking embarrassing. I was making more being an amateur for Lakai. But backed up against the wall, I had to sign this thing. I had no fucking choice.

I remember telling myself that all I wanted to do was be able to go out and  have the chance to  film for the Chocolate video. I remember getting bummed. It still wouldn’t of allowed me that. It would of been hardly enough to even cover rent. Well, if they would have even honored that goddamn contract. That was going to be the hell that I would of had to look forward to. But they didn’t. I was still loyal to them throughout this whole time. To this day, I run into kids that get psyched and think I’m some pro they like. Meanwhile, I’m out collecting scrap metal to sell so I can eat that night. It got that bad. The contract I signed was all just a ploy. They realized my shoe was doing well. It was the best selling in the line. They needed me looking like I rode for the company while they released another three colorways of shoes with my name on it every six months for who knows how long.

I remember going out to Vegas to help film that Kenny Anderson commercial. I was on the phone being like, ”Dude, I literally don’t have a penny in my pocket. I’m kind of sketched on traveling. I couldn’t even get to the airport if I wanted to.” But I still made that trip. But that bullshit fake contract ended up being just that. They wouldn’t live up to it. I got more excuses and stories month after month like, “The guy that needs to verify a check is on vacation. We don’t know when he’s getting back.” And me just like being so worked, telling them, “I’m literally hungry man. I need to eat.”

There I was “riding” for them, not getting paid, going through absolute hell, and then digging this hole of them coming down on me for not skating or getting shit done. It looked like exactly that from the outside as well. From that text, it took them over a year for me to ever get any type of help from them—which, by then, didn’t matter anymore. The first month, I couldn’t pay rent. By the third month, I was getting evicted. By the fourth month, I was stressing about how I was going to be able to afford storage. I was basically on the street. And in six months, it didn’t fucking matter anymore. I ended up selling and pawning every single thing I owned. I was fighting for my life, literally. To really put it in perspective, in those three years that I had that shoe out, there were two-and-a-half years that there was no way in hell that I would ever be able to get enough money together that would allow me to walk into a store and just buy a pair on my own if I wanted to. You can’t pay rent with street cred, and shockingly you can’t pay rent with a company pumping out over twenty different colorways of a shoe with your name on it either. The only thing I’ve ever wanted from them at the end of the day was just to have that chance. They never gave it to me. 

48 Blocks: So you lost everything? You had that woodworking studio in Brooklyn at one point.

Anthony: I lost my little clubhouse almost three years back. For two winters in New York, I was fortunate enough to have a place to hang out, make stuff, and just keep busy. It was definitely a cool experience, and taught me a lot of shit for as short-lived as it was. It’s been a while  since I’ve put time into anything creative besides skateboarding. It’s always enough to fill that creative outlet. But it never allows you to reach a point of feeling completely content, totally satisfied, or gets easy enough that you can wake up one day and it just bores you. I guess it could if you stop thinking. 

48 Blocks: Bill Strobeck has been putting out some clips featuring you. Are you still out filming with him?

Anthony: Yeah, he’s a friend. And that can go a long way, means a lot to me for some reason. He called me out of the blue one night when I was fifteen years old to see if I wanted to go hook up and go skate with him. The next day by 10:00 AM we were filming lines down by the Seaport. The rest is history, or on YouTube perhaps. Over the years, I’ve had the chance to film with some other people like Ty Evans and Aaron Meza. Honestly, it’s always felt like the same good vibe. I think if it hits the point where I’m actually filming with anyone, that kind of relationship / respect that I need has already been established. Bill also films really well, and has a style that has always been his own. That is a bonus. 

48 Blocks: I know it’s been talked about a million times before, but I have to ask you about  Brian Wenning.

Anthony: It has to be at least ten years since I’ve seen Brian. And I could no way in hell recall when or where that was. I really have no idea what he’s up to. I mean you hear little things every once in a while through the grapevine—an interview here and there. It seems like he went through a tough couple years of battling some personal stuff. He’s human. I would just want and hope nothing but the best for him—that he’s in a healthy and happy place. And I mean that.

48 Blocks: I saw you post a photo of your Chocolate portrait with different hairstyles on your Instagram account, and you made a comment about image.Do you feel like skateboarding is overly image-driven these days?

Anthony: Yes, it always will be that way. There hasn’t ever really been a time where it wasn’t. Sheep don’t ever try to mock or imitate humans. They can’t say the same about humans behaving like them unfortunately.

48 Blocks: What is your current status with Chocolate, are you still sponsored by them?

Anthony: Unfortunately, this little soap opera doesn’t have a happy ending. I wanted to thank anybody that has helped me in any way, shape, or form over the past 15 years with an extra special thank you to a few select people that have been there for the last two or three years. Unfortunately, the way life is, and people are; the difference is quite dramatic. These are the people that made sure I had a roof over my head at times. People that fed me when I was hungry. The last thing I have to do is list these people because they will know exactly who they are.   

The relationship that I have with Girl and Chocolate is the same one I’ve always had with them. It’s never been anymore or any less today than during any other time. It’s a group of people that I have an incredible amount of respect for. From the OG skaters that made something together better than anybody else that I grew up watching, to everybody currently on the team, to everybody behind the scenes.It has a very special history with how it started. All these things contribute in some way, all come together and produce something that, to me, has always been the best in skating. 

About 10 years ago, I made a decision that it was the only board company I would ever support, or want to be a part of in any way. So I quit the Workshop during a time you didn’t do shit like that. And contrary to belief, I never quit Alien to ride for Girl. It wasn’t anything like that. I just quit and went through a period of buying boards from the shop. I remember telling myself if they happen to give me this opportunity and reach out to me, I would be so grateful and psyched. Meanwhile, I had everybody I know calling me up telling me I’m crazy, don’t do it, try to get back on Alien. Nobody thought I would get on, and I didn’t give a shit. It was coming out of one ear faster than it was coming in. It had nothing to do with worrying about where my next check was going to come from. If they never would of reached out to me, that would of been it. Another company wasn’t an option. So I would of fully sabotaged my own career at the time. But I was lucky. A couple weeks later, I did get that call. This proves why it will always be different with them. I remember talking to them, and they felt super bad cause it happened to be real bad timing. It was early in the year, right after they did their budget. They said they would put me on, and give me a pro board, but not until the following year. They weren’t going to be able to pay me a definite salary. They would give me royalties. For close to a year it was like that. Them giving me that chance was all I ever wanted in the first place. I knew things would eventually fall into place. Right now, I still get boards from Chocolate. I don’t have any of my own boards out currently, and I shouldn’t until I put out of some type of video part and start getting more coverage. Nothing is more logical than those consequences. There isn’t an ounce of bad blood between us. Those guys are the last people I would ever point a finger at. Honestly, I don’t think they knew the severity of my situation over the past couple years. It’s exactly how I would be handling the situation if I were them.

I’m a person that’s pretty fucking hard on myself in a lot of ways. I’m a skater. That’s what I’m made of. I don’t run around pointing fingers and blaming others for my mistakes and fuck ups. Believe me, I have no problem taking the credit. It doesn’t change anything at the end of the day. It comes down to if the situation were different, would I have had a video part? It can’t be answered definitely, because I’m human. Who knows? Life is so random. Maybe I would have blew it somehow. But honestly, I would of placed my bet on yeah, of course I would have been able to film a video part. It’s the only thing I know how to do. I feel confident saying that I actually know how to do that. Would it have been a bunch of bullshit ollies and 50-50s, probably not. When have I ever done that? My last part was in the Lakai video, the first two tricks are back-to-back ollies, and there’s not another ollie in the whole part. I wouldn’t of placed my bet on that. But it’s pointless to speculate on something that can’t be changed.