Hugh was born in Montana in 1897 to parents William Henry Winslow and Josephine Whitaker Winslow. He had a sister, Irene, who was born in 1892. I don't know what became of her, but here's what she looked like when the family lived in Fort Collins, Colorado, circa 1920.
Hugh married Elizabeth Brady Ferguson (1904-1987) in 1939. Here's a strange photo of the newlyweds.
They had two children, Elizabeth Brady Cabot Winslow (1941) and Hugh Whitaker Winslow Jr. (1942). Again, I may have photos of Hugh Jr., but I can't say for sure. I do have photos of Elizabeth though. Here she is as an infant with her father.
And here she is later in life. The first three photos were taken at a Chanticlair photomat in Paris. The folder promises 6 photos in 6 minutes. There are only three left.
What I do know is that something went tragically wrong in Elizabeth's life. If you read the résumé that she posted in 2002, you'll see what I mean. I fear that she is no longer alive. It would be easy to read the résumé and laugh at her craziness, but if you view it in the perspective of the family history and the youthful pictures full of hope and promise, it's clear what a terrible tragedy this is. Elizabeth needed help, not ridicule.You can see more photos of the youthful Elizabeth here.
All of the West Point pictures as well as these and many others once belonged to Elizabeth. Some were in a manila envelope sent to her by her mother. We had others, including a box of her entire modeling portfolio, that were sent off to a paper auction in 2009 following my father-in-law's death. It's likely that he bought a lot of her belongings at a sale years earlier. I think we still have some modeling film footage though (updated - see below). In any case, somewhere along the line Elizabeth lost possession of all of these photographs, whether by choice or by accident I don't know.
Here's a short snippet of some sort of a modeling test film.
Here are some additional photos that are probably Elizabeth's ancestors.