A History of Short Words

From the New York Times Crossword Puzzle

REO

Mon, 5 Dec '22
Onetime manufacturer of the Flying Cloud and Royale
Tue, 20 Sep '22
___ Speedwagon
Sun, 4 Sep '22
Flying Cloud of old autodom
Thu, 5 May '22
___ Speedwagon
Tue, 4 Jan '22
___ Speedwagon
Sun, 29 Aug '21
Old auto with its founder's monogram
Sun, 20 Jun '21
Pierce-Arrow competitor
Tue, 16 Mar '21
Old car that's a homophone of another answer in this puzzle