I believe that it's just a straight nautical tie between Skipper's -- the chief of boats -- and the fact the manager is chief of the team.
The Team itself can be considered his boat.... I don't know if there was a specific incident that led to the popularizeing of Skipepr being used to term a manager, but the comparison between Captains of boats and Managers of teams shoudl be pretty clear.
The Baseball Hall of Fame has inducted 66 representatives of the New York/San Francisco Giants (55 players and 11 managers) into Cooperstown, more than any other team in the history of baseball. The Brooklyn/Los Angeles Dodgers are second with 45 players, 9 managers, and the Yankees are third with 41 players, 11 managers.
The cast of Racing Around the World Alone - 2010 includes: Boissieres Arnaud as Team Akena Unai Basurko as Skipper Bizkaia Yannick Bestaven as Skipper Aquarelle Jeremie Beyou as Skipper Deltadore Michel Desjoyeaux as Skipper Foncia Yann Elies as Skipper Generali Mike Golding as Skipper Ecover Marc Guillemot as Skipper Safran Derek Hatfield as Skipper Spirit of Canada Sabastian Josse as Skipper BT Roland Jourdain as Veolia Environment David Kinsman as Narrator Jean Le Cam as Skipper VM Armel Le Cleach as Skipper Brit Air Jonny Malbon as Skipper Artemis Kito Pavant as Skipper Groupe Bel Loick Peyron as Skipper Gitana Dinelli Raphael as Skipper Ocean Vital Vincent Riou as Skipper Prb Norbert Sedlacek as Skipper Nauitcasport Bernard Stamm as Skipper Poujoulat Dominique Wavre as Skipper Temenos 2
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