By many accounts, Pittsburgh-raised gambling entrepreneur Jakie Lerner was a very generous man — when the odds were in his favor. Like many of his peers who relied on betting in one form or another to make a living, Lerner had his ups and his downs.

When he was up, he liked to give friends and relatives gifts. He gave them dogs, cashmere sweaters, and jewelry. Lots of jewelry.

Last month I interviewed the daughter of another Pittsburgh gambling entrepreneur, a smalltime numbers operator who plied his trade in the city’s Strip District. He was friends with Lerner and Lerner’s daughter was friends with the woman, then about 10 years old. Lerner was a frequent visitor to their Millvale home during the summers he spent in Pittsburgh visiting from Tucson. Lerner caught up with friends and relatives, gambled, and checked in on the Hill District numbers rackets he oversaw remotely from Arizona.

In the interview with the Strip District numbers man’s daughter, she told me about one memorable 1950s visit by Lerner to their home. Lerner had bought a gold watch for his own daughter and he showed it to the friend’s daughter, asking if she liked it.

The young girl swooned. Seeing her reaction, Lerner gave her the watch and said he’d buy another for his daughter. Still living in Tucson, Lerner’s daughter told me in interviews in 2019 and 2020 that her father had given her jewelry. After speaking with the woman raised in the Strip District and Millvale, I texted Lerner’s daughter and asked if she recalled getting a watch from him in the 1950s.

“He did buy me several watches through the years but this one might’ve been a Hamilton that had diamonds around it. I still have the watch I don’t wear it,” she replied.