OK, better bust out a few since I started this thread . . .
many years back, we had a clueless guy draft Klaus Wilmsmeyer in about Round 5 or 6. At the time, Klaus was the PUNTER for the San Francisco 49'ers. Our scoring format at that time was a FG and TD ONLY scoring format, no performance scoring. There was not even a starting spot for Punters in our league starting lineup.
We had a guy draft Deion Sanders when he was playing DB for the Falcons. The league was NOT an IDP league, and only used Team defenses. This was well before any team had ever used Deoin for fill-in duty at the WR spot.