A History of Short Words

From the New York Times Crossword Puzzle

OWE

Mon, 1 Jul '24
The "o" of i.o.u.
Tue, 28 May '24
Be indebted to
Mon, 13 May '24
Have debts
Thu, 18 Apr '24
Be beholden to
Tue, 9 Apr '24
Have trouble with one's balance?
Thu, 1 Feb '24
Need to pay
Mon, 11 Dec '23
Have debts
Tue, 7 Nov '23
Have bills due
Fri, 29 Sep '23
Need to pay
Wed, 2 Aug '23
Be beholden to
Fri, 28 Jul '23
Be shy
Wed, 19 Jul '23
Not be square, say
Mon, 24 Apr '23
Be in debt
Thu, 23 Feb '23
Be behind, in a way
Tue, 3 Jan '23
Be in the red
Wed, 10 Aug '22
Carry a balance
Thu, 7 Oct '21
Be shy
Wed, 6 Oct '21
Be in a red state, perhaps
Tue, 5 Oct '21
What the middle of 58-Across stands for
Mon, 23 Aug '21
Have debts
Sun, 22 Aug '21
Word repeated in "I ___, I ___, it's off to work I go"
Wed, 23 Jun '21
Fall short
Mon, 14 Jun '21
Be in debt
Tue, 11 May '21
Have to pay
Sun, 2 May '21
Be short