I just attempted a re-count up until the present, but may have fucked up somewhere....
Sir Psycho - 23 pre 2015 + 9 more after = 32 winless drafts
Won the Footballing Duos & Partnerships draft with XabiArt in Feb 2017.
Followed by 9 more busts going solo.
El Lobo - 20 pre 2015 + 19 after = 39* drafts
Won the 2020 Summer Transfer Draft in August 2020.
*However, there was a controversial drawn final with him back sometime in 2016 which may or may not count as a win.
New entrants -
Max is on 17 with no wins (he started sometime in 2015, but has taken multiple breaks)
Tubby got up to an impressive 26 without a football draft win until he won Max's XI Degrees of Separation Draft in July 2020
Tubby did win the Cartoon draft back in 2016 though, thanks to the Thundercats, Inspector Gadget, Samurai Jack, Terrahawks, Ox Tales, and Godzilla.