Casady's fourth headmaster (1963-1980), Robert Bedford Woolsey , was born in Beloit, Wisconsin, on December 19, 1917 the second son of Theodore Dwight Woolsey and Mary Phoebe Bedford. His father was a country lawyer who instilled in his boys the value of education. In short, he required them both to go to Yale. Bob (to those who knew him as anything but "Dr. Woolsey ") graduated from Lake Forest Academy in 1934, and arrived at Yale three months shy of his 17th birthday. He earned his B.A. in Classics in 1938, and became an instructor at the Phillips Academy in Andover, Massachusetts.

Following the bombing of Pearl Harbor, he volunteered for military service, but was rejected. He returned to Andover to resume teaching, only to be drafted in the middle of the following school year. In what must have been his first glimpse at the perks of higher academic office, his headmaster phoned Secretary of War, Henry L. Stimpson, and won his deferment until the end of the term! He served in the Army Air Forces in WWII, where he was commissioned, sent to the Harvard Graduate School of Business, and became -- in his words -- a "90-day wonder." Bob taught at Yale after the war, and earned his Ph.D. there in 1950.

Sadly, his first marriage in 1941 to Helen Gilbert, of Beloit, ended with her death. He met and married Jo Anne Selleck in 1954, and adopted her 2-year-old daughter, Kathryn Taylor. By this time, Bob was the chairman of the Classics department at the Taft School in Watertown, Connecticut. He and Jo Anne had three other children in Watertown: Midge, Michael, and Robert. In 1963, Bob accepted the post of headmaster at Casady School -- which at the time was still a work-in-progress of the Episcopal Diocese, a re-purposed red-dirt prairie farm on the outskirts of town. With the support of a committed board of trustees, he supplemented his faculty with new recruits from top tier schools (several of them former students); standardized admissions; started capital and endowment campaigns; launched a construction effort that unified the campus (Lower Division up until that time was located at All Souls Episcopal Church); established primary and special education programs; and quietly integrated the student body in an era in which some state governors were openly defying Civil Rights legislation. He even mowed the lawns.

Over the next 17 years, Bob and Jo Anne worked together to mold Casady into one of the most highly-regarded college preparatory schools in the country. In the 30 years since his retirement, Bob enjoyed the role of elder statesmen, counseling subsequent headmasters on (but never interfering in) the myriad challenges of contemporary college prep education. The short drive up to 118th Street was a pilgrimage of sorts for the Casady faithful in the post-Dr. Woolsey years; the poolside martini was their solace.

In 2007 Bob, Jo Anne, and Michael moved to Morningside Ministries in Boerne, Texas (near San Antonio).

Bob died peacefully there on March 19, 2010, at age 92, survived by Jo Anne and their four children, four grandchildren (Allison Branch, David Martin, Caitlin and Sam Woolsey ) and one great-grandson (John David Martin III). From 1963 until his death, there was never a day that Casady was not near the fore of Bob Woolsey 's thoughts and heart. His ashes will be interred on the campus. The green fields and shady glades -- and the intellectual vibrancy they foster -- will be his monument. Donations can be made in his honor to: The Dr. Robert B. Woolsey Headmaster's Chair Endowment at Casady School, 9500 N. Pennsylvania Ave., Oklahoma City, OK 73120.