Harry L. Crosby
Singer Bing Crosby was part owner and vice president of the Pittsburgh Pirates. He first purchased stock in 1947, and owned it into the 1960's. In 1956, he signed Tom Mulcahy to a professional baseball contract (Bing, like Tom, had gone to Gonzaga University, so there was a connection). In 1957, the Commissioner of Baseball ruled that Bing did not have to sell some shares of Detroit Tigers stock which he owned along with his Pirates stock.
Bing played baseball in various leagues while a youth, according to "Bing Crosby: A Pocketful of Dreams". A friend remembered him as a better baseball than football player.