Often, when we think of different pro athletes that we are used to seeing with a stogie in hand, we think of basketball players or football players; golfers for sure, but do you ever think about a skateboarder? Probably not! Well, we have a pro skateboarder with us today who not only is a cigar enthusiast but had a skateboard deck created with a cigar band graphic on it. (We might actually have one to give away… wink wink)

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Jean: Timothy! Thanks for taking the time to chat today!

Timothy: My pleasure, thanks for having me


Jean: I came across your profile on Instagram. What got me excited, outside of a pro skateboarder being into cigars, was that you actually had a deck made with cigar graphics. Can you tell us about that?

Timothy: So I’m sponsored by a skateboard company called Strangelove. The graphic artist and co-owner of Strangelove sent me a text message one day asking me to send him a photo of myself holding a cigar. He said he had an idea for my next Board release and wanted to do something cigar-related because I’m heavy into cigars.

I didn’t know what to expect, but I was excited. When Sean showed me the finished graphic, I was stoked, so much so that I asked him if we could mock up some actual cigar bands with a box to use for a video I wanted to make to promote the board. Sean said his wife used to make fake cigars for movies all the time so it wouldn’t be a problem. Shout out to Sean’s wife, Donna, for hooking up the cigars and the box. It came out perfect.

 

Jean: So who are your sponsors?

Timothy: Uprise skateshop, Strangelove Skateboards, and DVS shoes. Hopefully, I can add a cigar company to that list soon, wink-wink.


Jean: And you live in Chicago, right? I love Chicago. Have you always lived there or off and on?

Timothy: Yes, I live in Chicago, and I’m born and raised here. I lived in Los Angeles in 2011, and I also lived in Los Angeles from 2014 to 2017. 

Timmy ollie over fence

Jean: What got you into skateboarding?

Timothy: What got me into Skateboarding was Tony Hawk’s first video game (Tony Hawk’s pro skater one) on PlayStation. That game came out in 1999; at that time, I was nine. I used to play that game every day after school with my brothers, and I was fascinated by how these characters were flying around on skateboards in all kinds of compromising ways. I had a little plastic fish skateboard from Toys' R ' Us, and after we would play the game, my brothers and I would go outside and try to do Ollies on that thing. 

I also remember watching X Games live where Tony Hawk did the 900 for the first time. Tony Hawk did the 900 before the video game came out, so maybe somehow Tony Hawk landing the 900 planted itself in my subconscious mind and when the video game launched, skateboarding manifested itself into my conscious reality, and now I’m a professional skateboarder. Thanks, Tony.

 

Jean: How did this turn into something professional for you?

Timothy: After the plastic fish board ran its course, my father got me a more sophisticated plastic skateboard from Toys “R” Us with a nose and a tail. It helped that somehow, a lot of kids in the neighborhood were into skateboarding, so my brothers and I would go to the local school parking lot and Skate with all the neighborhood kids. I remember the first time I saw somebody do a kick flip in real life. It was executed by a young man at the time whose name was Anthony Anelli. Some of the neighborhood kids also gave us VHS tapes of skateboard videos, and my brothers and I started watching those every morning before school. 

Two videos in particular we would watch religiously were “The Storm” and “Fulfilled The Dream” by Shorty skateboards. It was upon watching those videos every day that I decided to myself that I would become a professional skateboarder. I was 10 at that time. Since then, I’ve just dedicated myself to being the best skateboarder that I can be. I mostly focused on Street skateboarding and filming video parts. I started riding for Strangelove skateboards in 2018, and my first signature board came out in 2022. I also got my first shoe contract in 2022. That’s 22 years in the making. The moral of the story is follow your dreams.

 

Jean: Can you tell us about a moment that you are most proud of in your career as a skateboarder?

Timothy: There is no one moment that I’m most proud of; I’m proud of every moment I decided to step on a skateboard and put in work. It’s a combination of everything that makes me who I am today, and I’m grateful to have achieved one of my life’s goals. I’m proud to have the time and freedom to put forth my efforts in an activity I love so much, and I will continue to do so until the end of time.

 

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Jean: And what got you interested in cigars?

Timothy: My wife and I were introduced to cigars in 2023. We went to a farm that produces coffee, rum, honey, and tobacco. On a tour of the farm, we were shown how a cigar is rolled, and each person in our group was given a Cigar. I smoked that cigar, and from that point on, I have been fascinated and on the quest to learn about and smoke the best cigars the world has to offer.

 

Jean: What would you say is your favorite cigar of the moment, and when do you like to smoke a cigar?

Timothy: That’s a tough question because there are so many brands out there that make so many great cigars….. I have two answers for that question. My first answer is any Cigar that has a good draw, burns evenly, and has a flavor profile that puts a smile on my face. The second answer is the SP 1014 by Sanj Patel because I just finished smoking one, and that thing was nice. I like to smoke cigars in the morning with coffee, in the evening when I’m out skateboarding, at night when I’m sitting on my back porch, at the Cigar lounge with my Cuzin Ron, when there’s nothing to do, and when there’s everything to do. I like to smoke cigars anytime and at all times of the day for every reason. 

 

Jean: What inspired you to combine your skateboarding and cigar enthusiasm into the artwork on your deck with Strange Love?

Timothy: Just the fact that it relates to my actual personality and interests. And it helps that the skateboard is somewhat shaped like a cigar, hahaha. 

 

Jean: Well, we definitely think it is original and very cool. We actually bought one so that we could give it out to our audience. Do you think we could get it signed by you?

Timothy: Of course, it would be my pleasure.

Jean: You heard it here, folks! You can enter to win an authentic, signed Strange Love skateboard deck from Timothy Johnson here at Cigar World on our socials. Speaking of, Timothy, what are your socials so that the audience can follow you?

Timothy: My Instagram is @timothyjohnsonskate, and my YouTube channel is also @timothyjohnsonskate

 

Jean: Thank you so much for taking the time to chat with me today. Is there anything else you wanted to add

Timothy: Thank you, Jean, for having me here at Cigar World. It’s a beautiful place, and thank you to everyone who took the time to read this interview. Peace and blessings 

 


How cool what that?! Now you just need to head to Cigar World’s socials and enter into the contest to win that signed skateboard deck, and follow Timothy so you can keep up with what cigars he is smoking and what he is working on in his skating career. 

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