Caldwell rose to prominence when he announced that he would install a chairlift on his property. Currently under construction, the lift could be used to connect both Squaw and Alpine, although at this time the use of the triple chair is expected to be restricted to Caldwell's immediate friends and family and is not expected to operate until the 2009 - 2010 season. Under current regulations, a maximum of 25 people per day would be allowed to use the facility.
Caldwell also owns the land underneath two of Squaw's runs - Olympic Lady and KT-22. Caldwell purchased the property in 1990 from the Southern Pacific Land Company.
Caldwell has publicly stated that while he hopes that his property will become a ski area and that connections between his resort, Alpine and Squaw would be ideal, that regardless of what the future brings, he hopes to work closely with both Alpine and Squaw despite the litigation with that resort.
Squaw Valley's Vice President Tom Murphy has told the Sierra Sun newspaper that while linking Alpine and Squaw via Caldwell's land is "an exciting concept" that expansion is not "on the immediate radar."
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