Raymond F. Simon, 90, died peacefully at home on January 6, 2023. He was born on November 7, 1932, the youngest of six children of Peter Simon and Mary Doody and grew up in the Bridgeport neighborhood of Chicago. As the youngest, he was doted on by his parents and siblings. His mother died when he was 16 years old which may help explain why he treasured family and friends so much.
Raymond was educated at Catholic Schools, including Saint Ignatius High School (Class of 1950) and Loyola University and Loyola University Law School (Class of 1956). While an undergraduate at Loyola University, he met Mary Cassaretto, a fellow student. They fell in love and married in October 1956, and were blessed with eight children, Matthew (Jacqueline Covert), Mark (Dr. Catherine Counard), John (Tanya Solov), Gregory (Barbara Coghlan), David (Agnieszka Kubiak), Kevin (Micaela Daly), Maria (John Taylor) and Daniel, and 23 grandchildren. Raymond and Mary recently celebrated their 66th wedding anniversary.
After Law School, Raymond began working for the City of Chicago Law Department and quickly rose through the ranks. When Mayor Richard J. Daley appointed him Corporation Counsel, or Head of the City’s Law Department, in 1965, he was one of the youngest lawyers to ever hold that position. His work during the 1960s coincided with a tumultuous time in government and society during which the Law Department contributed to the City’s development in many ways. Raymond enjoyed the confidence of Mayor Daley and his colleagues in the City’s Law Department, including Richard Curry, Allen Hartman, Marvin Aspen and Daniel Pascale, each of whom went on to distinguished judicial careers. Raymond represented the City of Chicago’s interests during several sessions of the Illinois General Assembly and established life-long relationships with distinguished legislators, including George Dunne, John Touhy, Abner Mikva, Arthur McGloon, Paul Elward, Philip Rock, and Jeanne and Paul Simon. He represented the City in major trial and appellate litigation, including arguments before the U.S. Supreme Court. Working with the City’s Department Heads, Raymond learned about many areas of business and engaged with great professionals, including City Engineer James McDonough and City Architect Jerome Butler. He also made friends among leaders of organized labor, including Ed Brabec, who became head of the Plumber’s Union and the Chicago Federation of Labor. With the benefit of this experience, Raymond resigned from the City and launched a private law practice in partnership with Richard M. Daley in 1970.
Starting early in his career, Raymond worked with Mayor Richard J. Daley and the Democratic Party on political campaigns for many local, state and national candidates, including John F. Kennedy and Lyndon B. Johnson. After the 1964 election, Raymond accompanied Mayor Daley on a memorable visit to the White House where they dined with President and Lady Bird Johnson and discussed urban issues. Raymond enjoyed a close relationship with George Dunne and played a key role in his many campaigns for President of the Cook County Board of Commissioners. When George Dunne succeeded Richard J. Daley as head of the Cook County Democratic Party in 1976, Raymond became counsel to the Cook County Democratic Party. Raymond became close friends with many of George Dunne’s friends and colleagues, including John Stroger, Jesse White, Burton Natarus, Cecil Partee and Eugene Gordon. Neal Hartigan was another life-long friend, and Raymond worked on every one of his campaigns, including for Illinois Attorney General and Governor. Raymond also participated in many judicial campaigns, including those of his friends Richard Curry and Allen Hartman, and the Illinois Supreme Court campaigns of Daniel Ward and Mary Ann McMorrow, the first woman to serve as Justice and later as Chief Justice of the Illinois Supreme Court.
Raymond continued his public service through appointments to several government and non-government positions. During her mayoralty, Mayor Jane Byrne appointed Raymond first as a Commissioner and later as the President of the Board of Commissioners of the Chicago Park District. Raymond relished this assignment, engaging with many aspects of the Park District’s business and visiting park facilities and field houses throughout the City. George Dunne appointed Raymond to the Local Labor Relations Board which oversees matters related to public sector collective bargaining, where he served for many years and, with his fellow commissioners, worked to establish a proper balance between labor and management in the public sector. Raymond valued judges and the important role played by the courts. He thought Illinois judges were among the best and that Cook County Circuit Court and Appellate Court judges were the best of the best. He was a close friend of Harry Comerford, the distinguished Chief Judge of the Cook County Circuit Court, and served on a number of committees tasked with improving the quality and efficiency of the courts, including the Solovy Commission, chaired by his friend, Jerold Solovy.
Raymond enjoyed a long, successful career in the private practice of law, beginning when he left the City Law Department. His law partners and colleagues were like family, and in several cases were family members. Early on, Jack George joined Raymond and they worked together to establish the firm. Later, Gemma Allen, Joseph Spitalli, Laurence Suffredin and eventually, a younger generation, including Raymond’s sons, Matthew Simon and Gregory Simon, and Joseph Griseta, joined the firm. Raymond attracted a range of commercial clients, including Peoples Gas, Commonwealth Edison, McDonough Engineering, McKay Contractors, Helmut Jahn, Illinois Restaurant Association, Chicago Museums on Park District property, the Water Reclamation District and others. Raymond treated his clients like family and took great satisfaction in their success.
During his private law practice, Raymond had the opportunity to invest more time and effort in philanthropic causes and became more involved with several organizations. The Rev. Donald Hayes, S.J., then-President of Saint Ignatius College Prep, requested Raymond’s help as the school struggled with low enrollment and financial issues. Raymond turned to friends, clients, distinguished Chicagoans and fellow Ignatius alumni, including Ed Brabec, James O’Connor and James McDonough, to support their struggling alma mater with fund-raising. When Rev. Joseph Bowen, S.J., arrived as President in the mid-1970s, and recruited legendary entertainer Bob Hope to host a "Benefit For Ignatius," the team went to work selling sponsorships and tickets. Bob Hope brought along singer Andy Williams and actress Dianne Cannon and the Benefit was a resounding success. It became an annual event that supplemented the alumni auction and the Student Walk for Ignatius, which together with gifts from many generous alumni and supporters helped stabilize the school’s financial position. Raymond was one of the first non-clergy appointed to the Board of Trustees and initiated the school’s admission of girls and transition to a coeducational institution in 1979. He continued to work with Rev. Donald Rowe, S.J., Rev. Brian Paulsen, S.J., John Chandler, Walter Hansen and many others to support the school. All of Raymond’s children and many of his grandchildren have attended Saint Ignatius.
Raymond was devoted to Loyola University and worked with Rev. Raymond Baumhart, S.J., on many projects. He was part of the committee that recommended Nina Appel to be the first woman Dean of Loyola Law School. One of the ties that bound him to Loyola was Mary’s father, Dr. Frank Cassaretto, who taught Chemistry there for 42 years, and he honored that legacy by establishing the Frank and Agnes Cassaretto Scholarship For Chemistry Students. Later in life, Raymond was appointed to the Loyola University Board of Trustees where he served for ten years and worked closely with Rev. Michael Garanzini, S.J. While a Trustee, Raymond helped establish the Mary Cassaretto and Raymond Simon Chair of Constitutional Law at Loyola Law School.
Among the organizations close to his heart, Raymond became involved with Misericordia where he was inspired by Sister Rosemary Connelly, Lois Gates and the many families that embrace their vision of providing a supportive, nurturing environment and educational and vocational opportunities for children and adults with disabilities. Raymond was particularly moved when Chicago Theological Union conferred on him the Degree of Doctor of Humane Letters honoris causa, and, shortly before his death, bestowed its Diakonia Award on him and his entire family. Raymond also was a long-standing member and served as President of the Catholic Lawyers Guild which promotes fellowship and service in the legal profession.
Beginning in the 1980s, Raymond became involved professionally with two charitable foundations, The Helen Brach Foundation and The Polk Brothers Foundation, which exposed him to new perspectives on the role of charitable giving and its impact on education, social services and the arts. At Brach, Raymond worked with John Sheridan, James O’Connor, Rev. Donald Senior, Cherryl Thomas and others to impact education, generally, and Catholic education in particular, social services for people with disabilities, the homeless and those working for affordable housing, and programs to connect the arts and institutions with children and communities unfamiliar with those institutions. The Brach staff had a special place in Raymond’s heart, particularly Toni Perille, Marita Sullivan, John Hagnell and Lynn Griseta. At Polk, Raymond worked with Sandra Guthman, her fellow trustees, and a professional staff committed to promoting the arts and social welfare. He treasured these colleagues and their perspectives gave him a greater breadth of understanding and energized his outreach.
Raymond’s greatest joy was the family he built with Mary. Raymond made it home for dinner almost every night, where each of the eight children were encouraged to describe the events of the day and respond to Raymond and Mary’s stories about people and ideas. Frequently, guests were invited to dinner and their conversation enriched the family’s vision. When the boys got old enough to start fighting among themselves, Raymond and Mary purchased a property on Buffalo Lake in Central Wisconsin, so that the boys could run and play and swim and apply their energy to useful activities. During the Summer, Mary would stay at the property and Raymond would commute from Chicago for long weekends. This became the center of family life and Raymond discovered that he loved life in the country. Eventually, he bought ponies and horses so the children could learn to ride and care for animals.
Raymond and Mary conveyed values to their children through their example. They approached each day with joyful energy. They were curious about people and ideas, extended hospitality to friends and relatives, and made the family a source of fun, nurture and support. They loved to travel and explored Europe, South America, Japan, China and the Holy Land. They returned frequently to Mexico where they enjoyed dear friends. In later years, Raymond and Mary grew close to each of their children’s spouses and celebrated their grandchildren’s baptisms, birthdays and graduations. They hosted holiday celebrations at their country house for as many children and grandchildren as could make it, and Raymond would routinely shop and prepare meals for 30 or more people. Whenever possible, they would gather at the table and encourage each grandchild to describe the events of their lives and took the opportunity to instill their values of faith, work, kindness and service in a new generation.
Memorial visitation will be held at Church of the Holy Family (1080 W. Roosevelt Rd.) on Friday, January 20, 2023, 5:00pm-7:00pm and 10:00am the following morning. Funeral Mass will be held at Church of the Holy Family on Saturday, January 21, 11:00am, to be followed by a reception at Saint Ignatius College Prep (1076 W. Roosevelt Rd.) in Tully Hall 12:00pm-3:00pm. Burial will be private.
Eternal rest grant unto him, O Lord, and let the perpetual light shine upon him. May he rest in peace.