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The name "The Skye" was chosen for several reasons.  First and foremost was that the site of the building was the location of the Skye Hotel.  The hotel was built in 1903, during Bennettsville's heyday as a cotton capital.  The building, owned by Marlboro County entrepreneur A.J. Matheson, offered second floor rooms above street level retail businesses.  Matheson, the son of Scottish immigrants, named the hotel for the inner Hebridean island off mainland Scotland.  Among the first floor merchants were Sam Pearson Jeweler and Optician and Marlboro Drug Company.

The beautiful hotel's life was short.  It was destroyed by fire in 1908 after less than half a decade in business.  The fire took out the entire block of Main Street eastward from Marlboro Street.  The hotel was apparently a Bennettsville landmark during its short existence, appearing on numerous postcards from the era. 

The site was quickly rebuilt with the series of buildings that occupy the site today. C.V. Crosland built the three story building on the corner of Marlboro and Main.  Matheson order the construction of the adjacent buildings, including 210 East Main.  The street level was used as series of department stores.  The second floor was used in a variety of ways including extra retain space, apartments and finally as warehouse space for the department store below.

Allied Department store was the final tenant, operating until the 1980s.  The building was unoccupied for well over a decade and received no maintenance.  By 2002, a hole had developed in the roof, accelerating the decay.  Only drastic measures and a new purpose could save the old building.

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