There have been more painful losses. There have been more important losses. Pretty sure this is the dumbest, though.
Even after the three World Series championships, I still think about the bad losses. Scott Spiezio. J.T. Snow getting thrown out at the plate. Salomon Torres and Dave Burba. Ryan Spilborghs. A.J. Pierzynski hitting a ... hey, come back here, I'm sorry, hold on, wait.
The only way to get worse than April 25, 1986, though is to adjust for importance. Spiezio is worse because it was the World Series. Spilborghs is worse because it hurt postseason hopes.