All that winning... Trump endorsed not one but two Republican
candidates who ultimately lost their races.

Trump’s first loss came with Luther Strange, the former Alabama
attorney general who was appointed to take Jeff Sessions’ Senate
seat when Sessions became the U.S. attorney general. Trump backed
Strange in the Republican primary race for Senate, though he later
expressed some regrets about that decision.

“I’ll be honest, I might have made a mistake,” Trump said at a
September rally in Alabama. “If his opponent wins, I’m going to be
here campaigning like hell for him.”

Trump kept his word and endorsed the eventual Republican Senate
candidate, Roy Moore, even as multiple allegations of sexual
misconduct and child molestation plagued Moore’s campaign.

Trump reiterated his support for Moore as voters took to the polls
Tuesday morning.