You don't actually want to "win" the Pickett Trophy. But if you know of someone on Usenet deserving of the honor, here is how to nominate a potential recipient of this award, and how the recipient(s) are chosen.
Nominations are made publicly in the Usenet newsgroup alt.usenet.kooks. A typical nomination post should include the word "nomination" and the name of the award ("Pickett Trophy") in the subject line. The post can contain quotes demonstrating the nominee's worthiness of the award, such as refusal to quit or accept defeat, acknowledgement that he/she has zero chance of winning the argument, or other defiance in the face of reality. Nomination cycles for awards begin on the first day of each month, and are closed by the Vote Wrangler when voting begins. To appear on the ballot, the nomination must be seconded by an eligible member of the Usenet community within the voting cycle time frame. You may not nominate yourself for this award. Nominations are also subject to all other rules, regulations, and whims as set forth by the duly commissioned Vote Wrangler at the time of nomination.
Voting procedure changes from month to month on the whim of the Vote Wrangler. Keep an eye out for the official ballot as posted to alt.usenet.kooks newsgroup and follow the rules presented therein to vote. Votes are usually cast publicly by Usenet post and the polling period typically lasts from the first of the following month until the Vote Wrangler closes the ballot.
The joke is on the recipient. There is no physical "Pickett Trophy." You get your name posted in Usenet in the monthly award winner announcement, your name gets added to a couple Web sites including this one, and you earn the right to call yourself a Pickett Trophy honoree. But no actual trophy for the mantel.