Since resigning as its chief executive officer in 2001, Otten has been involved in numerous other businesses and industries, including the Major League Baseball's Boston Red Sox.
In 1980, he purchased Sunday River, and his company, LBO Resort Enterprises, grew by acquiring Sugarbush, Attitash Bear Peak, and Cranmore in the Vermont-New Hampshire skiing areas.
In 1995 he formed American Skiing Company by acquiring S-K-I, and this expanded his resorts to include Killington, Mount Snow, Haystack, Waterville Valley, and Sugarloaf/USA.
[citation needed] On February 28, 2016, The Boston Globe reported that Otten had purchased part of the now-closed Balsams Resort in Dixville Notch, New Hampshire.
[citation needed] From 2002 through 2007, Otten was vice chairman and minority partner of the Boston Red Sox American Major League Baseball franchise.
[8][9] The campaign was criticized by the Maine Democratic Party for allegedly copying President Barack Obama's famous "O" insignia and website layout from the 2008 presidential election cycle.
[12] Otten would be defeated the Republican primary by Waterville mayor Paul LePage, who would go on to win the general election and serve two terms as Governor of Maine.