James LeRoy Cupp (1978 – 2015)

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I met Cuppy early in my political career as I was rising through the ranks of the First District.  UVA graduate, University of Richmond Law, a love for seersuckers.

My kind of Virginian.

There’s a duo of pictures of us at the 2013 Republican Convention where he had switched his vote from Pete Snyder to E.W. Jackson, just a few hours before he was a dyed-in-the-wool booster of some other campaign.  I saw him sporting the Jackson hat and picked on him a lot for it.  “What are you doing. man?!?”

Apparently he had been convinced to support Jackson over Snyder… so I took a picture of him in his moment of weakness.

His response?  Take a picture back.

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For the next few months, this became a running joke on social media, as Cupp would post this picture whenever we had a friendly disagreement.  I suspect he was just gloating (worthily so) over picking the right horse in his moment of decision.

It was one of those convention stories that you would never get out of a primary — part of what makes conventions so awesome at the end of the day.  It builds a certain camaraderie that you simply cannot get otherwise, unless you have been in the trenches with a handful of folks.

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Cupp was one of the good guys; always chipping in, always the voice of reason, always the guy who knew where to cultivate friendships and discard with those who wasted one’s time.

In an era where true friendship and gentlemen are in rare form these days, James Cupp was a man who held on to the finer traditions of a Virginia gentleman.  A conservative par excellence, one who understood political combat, but a gentleman first.  We both had a great love for Virginia history — our last conversation being over Port Royal, Virginia and Belle Grove Plantation.  Missed seeing him for their 4th of July festivities by a whisker, too.

I really thought we had another 40 years of bourbon and gossip ahead of us.  Cuppy and Terrance will have to get a head start for the rest of us, I suppose.

Still floored…

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