Rick Shefchik provides a fun backstory on the photo above from his book From Fields to Fairways:

In the chapter on Midland Hills Country Club, I wrote about head pro Wally Mund’s efforts to keep the club afloat during the difficult war years. Because Mund was well-connected with the PGA of America, he was able to convince Bob Hope and Bing Crosby to stop at Midland Hills for an exhibition match while they were in town with the Caravan. Here’s the relevant passage from my book:

“On Saturday, May 9, 1942, the PGA sponsored a War Relief match at Midland Hills featuring Bing Crosby, Bob Hope, ‘Lighthorse’ Harry Cooper of Golden Valley, and Wally Mund. Hope and Crosby were part of the Hollywood Victory Caravan that was touring the country that spring to raise money for Army and Navy relief funds. Included in the caravan were Olivia de Havilland, Joan Bennett, Joan Blondell, Claudette Colbert, Charles Boyer, Cary Grant, Pat O’Brien, Merle Oberon, Eleanor Powell, Bert Lahr, Grouch Marx, Desi Arnaz, Stan Laurel and Oliver Hardy.

“Hope and Crosby tried to get in a round of golf at each stop. Despite appearing somewhat worse for the previous evening’s wear in the two most familiar photographs of this event, Hope beat Crosby one-up at Midland. the match was restricted to twelve holes because the entertainers were doing a matinee show at the St. Paul Auditorium, followed by an evening performance in Minneapolis.”

Rick also provided the photo above.  Thanks, Rick!