Remembering Barry Miles, a $2000 Challenge participant from year one

David S.
By David S. Wallens
Dec 6, 2022 | $2000 Challenge

Barry Miles, right, after claiming some $2000 Challenge hardware in 2005. He’s flanked by teammates Cliff Sebring Sr. (second from right) and Bill Cuttitta (second from left).

When we first announced the $2000 Challenge back in 1999–then capped at $1500–we wondered if anyone would join us for our unorthodox, budget-busting editorial exercise.

Barry Miles heeded that call, joining that inaugural class along with teammates Bill Cuttitta, Cliff Sebring Jr. and Cliff Sebring Sr. They came down to our Florida event from Maryland with a turbocharged, five-speed Plymouth Voyager that turned a 14.3-second time down the drag strip while finishing second overall. People took notice.

Miles and crew would return many times since–perhaps the closest thing to 100-percenters. No matter the year, a few constants: Come with a Dodge, leave with hardware.

Miles passed away December 5, 2022, from Glioblastoma brain cancer. He was 65.

He was creative, competitive and, and perhaps most important, kind.

From his sisters, Heidi and Deena, with the auto CV by Bill Cuttitta:

Eliot “Barry” Miles, 65, of Clinton, MD passed on Monday, December 5, 2022 after a six-month battle with GBM, Glioblastoma brain cancer. Optician; car enthusiast; humorist; audiophile with a proclivity for progressive rock; beer aficionado; loyal Washington football fan.

Barry was predeceased by his beloved wife Shelley Jo Glassburn Miles.  Barry is survived by his daughter and son-in-law Hillary Caye Miles and PJ Murray (Chesterton, IN), parents Carolyn and Forrest Miles (Melbourne, FL), brother Alan Miles (Palm Bay, FL), sister and brother-in-law Heidi Miles Tryon and Michael Tryon (Fairfax Station, VA), sister and brother-in-law Deena Miles and Kevin McHugh (Viera, FL), father-in-law Glenn Glassburn (Fredericksburg, VA), brother-in-law Scott Glassburn (Hampton, VA) as well as many dear relatives and friends.

Born in Orlando, FL, he grew up in Prince Georges County, graduated from Crossland High School and settled in Clinton, MD after his marriage to Shelley.  Barry and Shelley were married in August of 1978 at Beth El Hebrew Congregation in Alexandria, VA.  Barry has lived in his current home for over 30 years and added several garages to hold and maintain his collection of cars.

In 1980 Barry Miles, Optician and Dr. Forrest Z. Miles, Optometrist founded and co-owned Eye Design in Clinton, MD.  Father and son built a successful practice, working together for nearly 25 years. In 2009, the Opticians Association of Maryland (OAM) bestowed Barry with the Distinguished Optician Award. For almost 50 years, Barry enjoyed working with patients and informing them on the latest fashion and technological advancements in eyewear.

In the car community, there is a designation given to a unique, rare, or exceptional vehicle.  They are known as 1-of-1; Barry was truly 1-of-1.

Barry had a variety of unique sports and high-performance vehicles, including a 1970 Plum Crazy Purple Dodge Challenger T/A, 1986 Shelby GLHS, and a 2014 Stryker Green Viper SRT. He attended innumerable car shows and races, winning many awards such as the 2013 Grassroots Motorsports $2000 Challenge with his meticulously prepared cars.

As a car enthusiast, Barry held many volunteer and leadership roles in the following organizations: Sports Car Club of America (SCCA), BMW Car Club of America, Viper Owners Association, Shelby Dodge Automobile Club (SDAC). Barry also loved building and racing fast cars and he was valued as a highly skilled team member and crewed for Wesley Motorsports among other teams, and was instrumental to wins and trophies at races across the country, including the Pikes Peak International Hill Climb and Hot Rod Magazine Drag Week.  He also loved Formula One, and combined his love of adventure with his passion for motorsport by taking trips with family and friends to see races across the US, Canada, Germany, and Hungary.

Barry found beauty in everything around him.  He always dreamed of owning a log cabin and in September 2022, he was able to rent a beautiful log home on Lake Anna; there, loved ones shared a memorable week celebrating Barry’s life with him.  He was re-energized by the relaxing scenery, fun boat and truck rides, and loving family and friends.

Barry was selfless, passionate, and always willing to help family and friends. He was the life of the party!  Barry’s motto was the Monty Python quote “Always Look on the Bright Side of Life”.

Wanting to help others with the same cancer, Barry chose to donate his brain to the Anatomy Gifts Registry.  In lieu of flowers, please support your preferred cancer research organization.

Details to follow for Barry’s memorial celebration, Spring/Summer 2023.



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View comments on the GRM forums
drock25too HalfDork
12/6/22 12:34 a.m.

Never met him, but sounds like a cool guy. God Speed. 

David S. Wallens
David S. Wallens Editorial Director
12/6/22 12:37 a.m.

In reply to drock25too :

He was way cool. 

May his memory be a blessing. 

SV reX
SV reX MegaDork
12/6/22 1:13 a.m.

No!! cryingcrying

Barry was one of my favorite Challenge people. That makes me really sad!

Rest in peace friend. 

John Welsh
John Welsh Mod Squad
12/6/22 5:28 a.m.

A great guy and definitely "Challenge Royalty"

To his Challenge teammate and equal Challenge Royalty,  Bill Cuttitta, I'm sorry for your loss of such a great friend!

Stampie GRM+ Memberand MegaDork
12/6/22 6:37 a.m.

Damn I knew it wasn't going well when they told us at the Challenge but I was hoping for the best. Thoughts for his friends and family. 

DeadSkunk  (Warren)
DeadSkunk (Warren) UltimaDork
12/6/22 6:39 a.m.

Damned cancer......we lost one of the good guys today. Condolences to his family and to you, Bill .

Floating Doc (Forum Supporter)
Floating Doc (Forum Supporter) GRM+ Memberand UltimaDork
12/6/22 7:08 a.m.

Being a latecomer to the Challenge, I wasn't fortunate enough to have known Barry. He certainly had a great run, and would make a role model for any of us. 

My condolences to all those who knew and loved him. 



QuasiMofo (John Brown)
QuasiMofo (John Brown) GRM+ Memberand MegaDork
12/6/22 8:34 a.m.

Thank you for being you Barry. You have left an indelible mark on the souls of many. 

David S. Wallens
David S. Wallens Editorial Director
12/6/22 9:13 a.m.

And a few pics of Barry from over the years:

David S. Wallens
David S. Wallens Editorial Director
12/6/22 9:14 a.m.

Danny Shields (Forum Supporter)
Danny Shields (Forum Supporter) GRM+ Memberand HalfDork
12/6/22 9:28 a.m.

Barry was one of the people who made the Challenge special, right from the start.  

Thanks, David, for a nice writeup on a very interesting guy. 

alfadriver GRM+ Memberand MegaDork
12/6/22 9:47 a.m.

Cancer sucks. 
That is some bad news, and we will remember him well. He was part of a great team, and it was a pleasure to compete with them. 

AngryCorvair (Forum Supporter)
AngryCorvair (Forum Supporter) GRM+ Memberand MegaDork
12/6/22 10:14 a.m.

RIP to a great dude. 

Patrick GRM+ Memberand MegaDork
12/6/22 10:45 a.m.

Rest in Power brother 


never had anything but completely smile fueled positive interactions with Barry. 

Tom Suddard
Tom Suddard GRM+ Memberand Director of Marketing & Digital Assets
12/6/22 11:32 a.m.

Rest in Peace, Barry.

He is a big reason that the culture and community around the $2000 Challenge is as strong as it is today, and he was a heck of a person and a heck of a racer. 

Billy_Bottle_Caps GRM+ Memberand SuperDork
12/6/22 12:03 p.m.

So sorry to hear this, RIP sir.



Byrneon27 GRM+ Memberand Reader
12/6/22 7:28 p.m.

This one hurts there's been a lot lost from our world these last few years but this one... 

Barry and Cliff came to a neon/turbo dodge meet I help to organize a million years ago some of the best people I've met doing car stuff. 


JG said at the challenge being privileged to know so many wonderful people means eventually having to say goodbye to them something about it really resonated with me. 

Tony Sestito
Tony Sestito UltimaDork
12/6/22 7:49 p.m.

I met Barry at the $2009 Challenge. My friend Greg and I were there with a turbo Miata he had scraped together, and we had no idea what we were getting into. Once I saw the Shelby Dodge guys (I think that year, it consisted of Barry, Bill, and Pat Culkin) scoot a turbo Dodge down the track at absurd speeds for next to nothing invested, I had lots of questions. After the banquet, I cornered them outside in the hotel hallway and asked away. All three of them spent as much time as I needed answering all my questions, and eventually influenced me to buy my own Shelby CSX when I got home! 

In $2010, we returned, and I again cornered the Shelby Dodge guys and told them what they influenced me to do. After some laughs, we spent some time hanging out, and I got to know them a bit. At each Challenge I returned to, we made a point to hang with them. We even traded parts and tools a few times to keep each other going when stuff broke. Their friendship mirrored the friendship I have with a few of my Challenge teammates, so we clicked instantly. 

Barry was such a nice guy and a true GRM'er in the best ways. He was always gracious, knowledgeable, and just plain fun to be around. He will be missed greatly. 

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