John Ashcroft was the Attorney General under GWB, but his background story is awesome.
https://en.wikipedia.org/wiki/United...Missouri,_2000
In the year 2000, incumbent US Senator Ashcroft considered a bid for the Presidency but decided to rerun for the Senate seat.
His opponent, Democrat Governor Mel Carnahan. During this tight race that included Ashcroft outspending the Governor by a lot of money. Carnahan died in a plane crash three weeks before election day.
Election day results:
Mel Carnahan -- 1,191,812 (50.5%)
John Ashcroft -- 1,142,852 (48.4%)