Owners of the 16-story Jack Tar Hotel (formerly Washington Duke Hotel, later Durham Hotel) decided in the early 1960s that their 1926 facility was due for modernizing, and built a motel-style addition opposite the Jack Tar's main entrance on Corcoran Street.

Opened in 1963, the addition included a parking garage and a rooftop courtyard with a swimming pool. A glass-walled pedestrian bridge connected the addition to the older building.

The hotel, growing increasingly obsolescent and prohibitively expensive to upgrade, was demolished in 1975. The addition's sidewalk storefronts remain occupied and the parking garage has operated continuously since its opening. The upper floors are vacant and the swimming pool is in a prolonged state of disrepair.

The addition is popularly known as the "Oprah Building" because of a banner its owner, the late Ronnie Sturdivant, hung on its Corcoran Street side for years. The banner read "We want Oprah," referring to Sturdivant's wish that television personality Oprah Winfrey would pay Durham a visit.