This story first appeared in the July 25 issue of The Hollywood Reporter magazine.
Bing Crosby ranked among the wealthiest entertainers of his era and was an early, highly successful multihyphenate.
The singer-actor-entrepreneur sold a half-billion records; did a string of hit movies with Bob Hope; won a best actor Oscar for 1944's Going My Way; and in 1948 invested in a "fast freezing" process that paid off handsomely when it became Minute Maid. By the late 1950s, his wealth was estimated at up to $130 million in today's dollars. But the investment that got the most attention was his 1946 purchase of a 25 percent stake in the Pittsburgh Pirates.