While we're on the subject of fool of the year, I challenge your nomination, and nominate myself. It didn't end up with a rebuy thank goodness, but it's monumentally stupid - like the Frank Spencer of space.
So I'm bounty hunting in a Nav beacon, grinding rep for Sirius Corp, and I'm doing well, lots of ship kills. However a few ships made me use my SCB, and my Python massively overheats when I'm all guns blazing and firing off a shield cell... So I inevitably run out of cells, and here is where the fun starts.
A rookie power management error, and my shields go down. The massive overheating from all the shield cells has left my canopy with so little integrity that it blows out immediately. Undeterred, I finish off the Fed Dropship, and head out to the only station in the system - 2000LS away, and an Outpost.
With 2 minutes of oxygen remaining, I dock and... THERE'S NO REPAIR FACILITIES AT THIS OUTPOST.
Panicking, I quickly went into the hangar to restore my atmosphere and checked outfitting for a higher rated life support... Only C... Still, it's better than the D I've got, so I buy it and start frantically searching the galaxy map for systems with nearby stations to the entry point.
Thankfully I find one, jump to it, dock and repair with another 2 minutes remaining - what a ride! What a moron.