The Pickett Trophy was proposed to Usenet on July 5, 1999, in the following Usenet post:

To complement the Col. Custer "Kicked Ass" Award, I propose creation of a new Kook award, the General George Pickett Trophy for Valiant, Stupid Futility. This award is named for General George Pickett, Confederate general who led the infamous "Pickett's Charge" and accomplished absolutely nothing except the transformation of live soldiers into dead soldiers. The General Pickett Trophy would be awarded to the Kook who launches a crusade so obviously in the wrong, so doomed to failure, so likely to result in abject misery, and clings to it until the Grim Reaper was to tap on his shoulder and ask him to slow down. Voting would be by acclamation, awarded the same as the Custer "Kicked Ass" award.
Examples of worthy recipients:
- US Sen. Murkowski's "Spam Is Good" crusade
- Bill Palmer's drive to amass the largest personal archive on Deja News
- Steve Case's desire to make AOL respectable

The creation of the Pickett Trophy was approved and it was placed on the ballot for the July 1999 voting. The first winner was Brad Jesness, who ran unopposed for the honor and received it on August 17, 1999.

Gen. Pickett