She was sired by King James, the 1909 retrospective American Champion Older Male Horse|.
My Dear's dam was Bettie Landon making her a full sister to Admiral Cary T. Grayson's very good colt, My Own.
At age two, My Dear raced and won in Maryland for H. Rozier Dulany but was sold to G. W. Forman in November of that year.
Her performances earned her retrospective 1921 American Champion Older Female Horse honors.
In November 1923, My Dear broke a bone in her leg that ended her racing career.