No, you are the one who makes no sense. The Iver Johnson Trailsman 66 came out in 1956. The Depression was pretty much over when WW II broke out in the late 1930s and early 1940s.
I also doubt a cop of any size jurisdiction would carry a .22 as a service pistol, but he might have been in a small town where anything in the holster would do.
Probably worth more than $75, these days. People will buy anything.