The first shot shows Wayne Woodward with a pretty good looking sprinter. Wayne used the name Billy Hughes both on and off the track for a period in an effort to cloud his past. Wayne went on to own a couple of Indy cars although he never managed to get one qualified at Indianapolis. Rootie, I could be wrong about the next photo but I think this may be Joe James 1950 entry which was a DNQ. That's some pretty unique artwork on the side of the car. I wonder where that came from? Wild for 1950. BTW, that looks like a pneumatic starter for one of the Novis on the cart in front of the #63 car.
The #63 has some interesting history. Originally it was Leo Dobry's City of Tacoma Spl. driven by Hal Cole in 48 and Jack McGrath in 49. In 1950 it was sponsored (in part at least) by Bob Hope and Bing Crosby. It seems they were partners in building a new golf course in Spokane Wa. called the Esmaralda Country club and the logo of the club was the horse head, thus the artwork.
FOUND the correct photo for this caption Bob Welborn with the Plymouth he drove on the NASCAR Cup circuit for car owner J. O. Goode Loudbang thanks for going to trouble of finding correct pic. 1 more car I promise, Rex Winter Dry n windy Lubbock TX
Chicago’s I-290 expressway, also known as the Eisenhower. The photo shows the eastern terminus of the road with the area known as the Loop, Chicago’s downtown area and Lake Michigan beyond. Somehow, when the old Main Post Office was designed in 1921 the architects had vision and designed it so a roadway would pass through. The photo by @HEMIDAV shows an entrance ramp at the upper right, with an exit ramp next to it. Only some of the entrance and exit ramps are on the left side of the flow of traffic, a design brought about by the tight right of way for the road. Those entrance ramps can make for some exciting merging, visibility is limited.