Galimore possessed incredible speed and lateral movement; many of the opposing players of the time stated that they believed Galimore could run side-to-side down the field just as fast as most men could in a straight line. His running style could be said to most resemble the style of Billy Sims or perhaps Terrell Davis, but faster.
In a documentary short by NFL Films on Galimore, it was said that he was probably the last great find before NFL scouting became sophisticated. Bears assistant coach Phil Handler, while scouting for talent in Florida, received a tip about Galimore's prowess as a halfback, and the Bears subsequently drafted him in the 5th round of the 1956 NFL draft. Galimore's peers (including Chuck Bednarik and Doug Atkins) referred to Galimore as one of the best runners they ever faced.
Galimore was killed in an automobile accident on July 27, 1964 in Rensselaer, Indiana at the age of 29 with teammate Bo Farrington. His number 28 has been retired by the Bears.
His son, Ron Galimore, was the first Black U.S. Olympic gymnast.
Willie Galimore's last visit to his hometown of St. Augustine, Florida came just weeks before his death, and he participated in civil rights demonstrations there, becoming the first Black person who was able to register as a guest at the previously all-white Ponce de Leon Motor Lodge (where the arrest of the 72 year old mother of the governor of Massachusetts for trying to be served in a racially integrated group had made national headlines a few months before). Galimore's civil rights activism is honored with a Freedom Trail marker at his home at 57 Chapin Street in St. Augustine. His widow, Mrs. Audrey Galimore, took part in the dedication of the marker on July 2, 2007. A community center in the historic Lincolnville neighborhood of the city also bears Galimore's name, and he is depicted on a historical mural painted by schoolchildren on Washington Street.