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The North Carolina Country Club was Siffords first job. Sifford was born in Charlotte, North Carolina in 1922. He began work as a caddy at the age of thirteen. He would earn roughly 35 cent per day and start learning the in's and out's of golf. This made Sifford who he is today because as he got older the Country Club kicked him out because he was to intimidating for the white golfers.

Alexander, the owner of the golf club told Sifford that the best choice for him is to leave the club. At first Sifford was mad and discouraged because the same person who taught him the game was kicking him out. Then later in life he noticed Mt. Alexander was doing what was best for him so he didn't get hurt or targeted moved to Philadelphia when he was 17 years old, where he played against local Black golfers.

Sifford began golfing professionally in 1948. He competed in the golf tournaments that Black golfers organized for themselves as they were excluded from the Professional Golfers' Association of America.