A History of Short Words

From the New York Times Crossword Puzzle

ANGLE

Tue, 8 Aug '23
Point of view
Tue, 22 Nov '22
Right ___
Mon, 10 Oct '22
What a protractor measures
Sat, 4 Jun '22
It's a matter of degree
Tue, 28 Sep '21
Relationship of the circled letters to the apt words they connect to in this puzzle