Richard Daniel O’Connor III died peacefully, surrounded by his children, on March 14, 2022, bringing to an end an unconventional, wholehearted, and loving life. He was 76 years old.

 

Richard was a deeply spiritual man with a playful sense of humor and a drive to serve others through his work. In a final gift to his family, he maintained a positive, cheerful attitude to the end, joking with his hospice nurses and praising his children for their love.

 

Richard was born to Mary Aurelia and Richard D. O’Connor Jr. of Highwood, Illinois, on December 27, 1945, the fourth of ten children.  A talented athlete and eighth-grade class president, Richard followed the path of many promising teenagers in that era -- toward the priesthood. He left the seminary after 2-1/2 years, but the experience instilled a lifelong love of music and reading, and an appreciation for the power of prayer – a capacity he would extend later in life to practicing meditation.

 

Richard finished high school at Loyola Academy in Wilmette, Illinois, where he excelled in football, averaging 8.5 yards a carry as a halfback. Asked why he ran like a man possessed, Richard cited the “sheer terror” of facing 230-pound defensemen when you’re only 5-feet-9 and 145 pounds. He turned his size to his advantage in baseball, his first love. After he stole six bases during a Catholic League All-Star game at Comiskey Park, the Chicago Tribune called him “the Mercury of the Catholic League … as fearless a base thief as the great Maury Wills.” 

 

Richard graduated from the University of Notre Dame in 1967 and earned a Ph.D. in education from Northwestern University. As Richard’s advisors at Northwestern noted, he was driven to love others through his work. He hoped to make a difference in education. During a stint as a teacher, assistant principal and coach at Loyola Academy, he took satisfaction in being known as a very good teacher. Decades later, former students who spotted him on the street in Chicago were still greeting him with delight, yelling, “Hey, Mr. O’Connor!” 

 

A dismal job market in education led him to shift to working in business, where his charm and persuasive skills served him well. As an account executive for a major insurance brokerage company, Richard earned a reputation for saving big, troubled accounts. He accomplished this by facing angry gatherings of fast-food franchisees, physicians, and other clients and persuading them not to take their business elsewhere. He also won awards for direct-marketing campaigns and helped develop new insurance products.

 

But his proudest achievement, Richard often said, was his kids. He liked to say that his five children, born between 1969 and 1990, earned him a distinction as “the Minnie Minoso of fathers” – likening his four-decade fatherhood record to the star third baseman’s five-decade baseball career. Richard was playful with his children, taking them on bike rides when they were small and asking them to watch for “the big rock candy mountain.” He loved flying kites on the beach year-round or playing in the yard with his children. Later, he loved taking his kids to White Sox games, arm-wrestling with them, or teaching them to play poker, a cigar clenched between his teeth and a tweed cap pulled down over his eyes.

 

Richard had a generous and caring heart. If you mentioned that you liked his jacket, he was likely to take it off and give it to you. He was always inclined to help people less fortunate than he. He devoted many afternoons and evenings to service work inside prisons, helping inmates better their lives. He also used his management skills on behalf of the poor, chairing a nonprofit board during construction of an innovative long-term-care facility for the homeless. 

 

Richard had yearned to head West ever since watching the Lone Ranger on TV as a child.  He realized his dream at age 47 by moving with his family to Portland, Oregon. There he satisfied a spiritual yearning, to practice Tibetan Buddhism with a great Buddhist teacher near there. 

 

He realized another dream, by finally managing to build a career in education. Acting on his eye for the needs of the underserved, he founded a new high school, the Academy for Architecture, Construction and Engineering, to serve at-risk students who weren’t college-bound but loved working with their hands. Founded upon an extraordinary partnership among four school districts, several trade unions, and a staunchly anti-union construction-industry group, ACE Academy prepared students for high-paying apprenticeships straight out of high school. The school was lauded by industry groups as a national model for vocational education, and all involved credited Richard for his vision, hard work and ceaseless fundraising. As one education official said, “Dick works tirelessly for issues he believes in.” 

 

Known to his seven grandchildren as “Grandpa Silly,” Richard loved dressing up as Santa Claus at countless public and private events and telling jokes on himself afterward. In a blessing to his family, his playfulness continued through the end of his life as he joked with his caregivers and made light of his pain.

 

His loved ones took great comfort in his peaceful acceptance of end-of-life hardship. After decades of practicing prayer and meditation, studying Buddhist teachings, and striving for acceptance, Richard clearly had found inner peace. 

 

He is survived by his five children, Margaret Wade (and John Luczak), Richard Daniel IV (and Emily), Lucas (and Papatya), Cristin, and James (and Alexandra); his seven grandchildren, Mary, P.J., Frances, Silvia, Ramona, Bella and Abby; and his eight siblings – Mary Beth (and Gerald) McGivern, Sophia, Nick, Kathy (and Michael) Schell, Michael (and Jacque), Timothy, Colleen (and Steve) Schwanz, and Kevin.