Very interesting question.

I know, when I first got Hollingsworth's Truman, that was in July of 1990.

I bought Patrick's Rio I think in November of 1990, and Patrick had La Bamba (Rolo x Red Baby) on his yard at the time (I took the photo on his pedigree in 1990).

La Bamba would be a sister to the dam of your posted dog, Fifty Three's Sugar Baby ... and La Bamba was a full-grown dog in 1990 (and a retired 2xW, 1xD), so he had to be at least 4-5 years old in 1990, minimum.

Sugar Baby, La Bamba's sister, supposedly gave birth to Little Trouble in 2002, which would make her at least 16-17 years old at the time, minimum.

Doesn't sound very likely does it ...

Good catch!

Jack