Born into an old New England family, Clegg grew up in Rhode Island, and during his early years developed strong interests in railroads, electronics, and photography.

During the lavender panic, the two moved in 1950 to Virginia City, Nevada, a tiny community that had once been a fabled mining boomtown.

Beebe and Clegg shared a renovated mansion in the town, and also owned a private railroad car, redone in a Victorian Baroque style.

Beebe left the bulk of his $2 million estate to Clegg (with provision for T-Bone Towser II, their Newfoundland).

It is likely that Clegg's contributions were primarily photographic in nature; his images were known for an expressive quality that helped broaden the artistic scope of railroad photography.