Cobert recently made good on his bet, live streaming his tattoo session on Facebook and inviting cameras from WQAD-TV to document the fallout from his painful election loss.
"I'm thinking about my life and how it went wrong, and now I'm getting a Trump stamp," Cobert said while getting inked.
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The tattoo design -- a caricature of Donald Trump -- was picked by Cobert's Facebook followers, as was the location: his lower back.
Perhaps you could call it a Trump stamp?
"This is definitely the stupidest thing I've ever done for views," he said of the experience.
Even after hours of work, the tattoo still isn't complete. Cobert has to return at a later date to have color added.