Wilfred Drennen Whiteside was born on November 24, 1905 to parents Dr. Thomas Forrest Whiteside and Mattie Elson Oslin in Timpson, Texas.  He had four siblings, Forrest Whiteside (1899-1899), James Whiteside (1901-1902), Thomas Forrest Whiteside (1901-1973) and Sidney Joseph Whiteside (1903-1977).  Wilfred graduated from Timpson High School in 1926.  He played football at Timpson and was team captain in 1924.  His gained the nickname "Hoss" while playing ball in the fall of 1922 at Timpson, a nickname he kept for the rest of his life.

At the age of 20 he married Tommye Eugenia Bell on April 25, 1926 in Nacogdoches, Texas, one month before graduation.  After graduation, the couple moved to Houston where he attended Texas Dental College, graduating valedictorian in 1930.  He was also winner of the faculty diamond medal, awarded to the graduate making a general average of 95 or over in all subjects, including practical work, the third recipient in the history of the school.  In 1932, they returned to Timpson where he opened his dental practice.  Tommye and Wilfred had three children, Forrest James Whiteside (1930-1930), Wilfred (Billy) Drennen Whiteside (1931-2014) and Barbara Sue Whiteside (1933-2015).  Children Billy (Class of 48) and Barbara Sue (Class of 50) both graduated from Timpson High School.

An interesting side note supplied by his granddaughter, Lee Ann Whiteside Krieg:   Hoss enlisted in the U. S. Marine Corp on March 21, 1922 at Parris Island, South Carolina, but was honorably discharged 10 days later for under-age enlistment.  He and his brothers, Sid and Thomas, spent the early part of 1924 mining copper in Arizona.  He came back from these adventures to finish high school so he could continue on to higher education.  

Dr. Whiteside died at a relatively young age of 50 on May 31, 1956 in Timpson and was laid to rest in the Woodlawn Cemetery.