Pied Piper has been synonymous with sailboat racing since late 1971.  It started with Richard Jennings who began sailing as a boy in Chicago’s Jackson Park Harbor.  From humble beginnings Jennings became a world champion helmsmen.  Through the years many great sailors such as Lowell North, John Rumsey, Ted Turner, Buddy Melges, Rod Davis and  Tom Blackhaller have contributed to the story and success of various Pied Piper campaigns.  In 1975 Dick Jennings and Lowell North won the North American and World One Ton Championships. At that time, those were two of the most prestigious awards in sailing.  In 1987 Pied Piper set the course record for the Chicago to Mackinac Island race.  This record had stood for over 76 years.  Pied Piper has been first to finish in that Chicago to Mackinac Island race 6 times, this is more than any other boat in the over 100 year history of the race. 

Richard Jennings sailed in locations all around the world from the famous Sydney to Hobart race where Pied Piper placed 2nd overall to Southern Ocean Racing Circuit with numerous top finishes, to the Caribbean Circuit winning the big boat division in 1998. 

In 1995, at the age of 15, Jack Jennings began sailing with his father in the Chicago to Mackinac Island race.  In 1996 Pied Piper recorded its sixth "first" to finish award beating newer and supposed, faster competitors to the Island.  In 1999 Pied Piper won the Chicago Mac race overall with Richard and Jack Jennings beating the fleet to the Michagan shore and leading the remainder of the race to the Island. In 2005 Richard Jennings retired from sailing to pursue other interests.  The Pied Piper legacy has remained competitive and relevant in Sailing through the efforts of Jack Jennings.

Jack has continued to campaign under the Pied Piper name at various events around the world. Pied Piper Racing LLC will allow the tradition of winning, innovation and sportsmanship established by Richard Jennings to continue for many years to come.