It was a little more than two years ago when Stanley Samuel Penn, the last man standing in what was once San Diego’s widespread card room industry, stood quietly in the spacious courtroom of U.S. District Court Judge Roger Benitez.

Penn was there to enter a conditional guilty plea for his role in a sports gambling ring that operated out of the Lucky Lady Card Room and Casino, a small 11-table operation on El Cajon Boulevard near 54th Street that Penn had owned for more than four decades.