I've mentioned that Holperin is the first state legislator to face two recall elections while serving in the state legislature. There have been others that have faced two recalls in their career. But I only know of one person who has actually lost two recalls.
Portsmouth, Virginia Mayor James Holley III served two separate terms as mayor. He was recalled and removed in both of them. Holley was first elected in 1984 and was removed in 1987. (According to the Wikipedia link, he was the first official to be removed by recall in Virginia. I don't know when Virginia adopted the recall for local officials). He staged a comeback in 2008, only to be kick out in 2010.
Thanks to the Dave Foster at the Virginian-Pilot for this tip.