Sort of the counter to the most wins ever, no championships.  These guys make the game look easy.
I know of 2 in the recent past.   Any more?

Phelan Season 64 -   UNA HOOPS at E. Texas Baptist

Wooden Season 68 -  BFIFE at Chicago

In Bfife's instance, he came, he saw, he conquered, he left.  Not sure what he did with the points because he is no longer active and even if he took Amazon money, there'd still be some left.

Wooden Season 38 - toysboys at George Fox

I only lost one game that season, and then I ended up beating him the second time around for the championship.  I remember recruiting two drop down transfers before the season to fill my 2 empty spots.  I was one and done too as I went to D2 the following season and ended up winning a championship there after a few seasons.  I'm now at Duke where I hope to win a D3, D2 & D1 champtionship all in the same world, under the same username.  Don't know if anyone has done that before.....

was that your first season anywhere or just in wooden

Caveat to all of this is that the 2 above and any other's contributed could be an alias for an established coach but no indication they were at this point

First in wooden. I already had a team in another world. I don't know how long ago season 38 was, but I joined the site in January 2009.