Neutral
Winston Calvert
Areas of Expertise:
Business Litigation, Commercial, Constitutional Law, Construction, Consumer, Contracts, Employment, Environmental Law, Insurance, Media Law, Personal Injury, Products Liability, Real Property, Toxic Torts
Services:
Mediator, Arbitrator
Winston Calvert has negotiated resolutions to many of the most complex disputes that arose in the last two decades in the St. Louis region. His experience holding significant leadership roles in the private, public, and nonprofit sectors give him a unique ability to guide parties through conflicts, find common ground with their foes, and navigate obstacles that would otherwise prevent a settlement.
As an attorney, Calvert helped solve multidimensional problems clients faced. He has led clients to successful resolutions that required overcoming bet-the-company lawsuits, negotiating multibillion dollar transactions, and navigating media coverage and reputational risks. His work has earned accolades including Missouri Lawyer’s Weekly naming him the “Legal Champion of the Year,” being listed as one of the “Top Bet-the-Company Lawyers in Missouri,” and being named to SuperLawyers several years.
Successful resolutions he engineered include resolving the St. Stanislaus Catholic Church’s dispute with the Archdiocese of St. Louis, a dispute that began in 1888 and resurfaced every decade until its resolution in 2013. The St. Stanislaus experience will be the subject of a forthcoming feature film titled The Faithful, penned by an Emmy-award winning writer and produced by Laurene Powell Jobs. He also negotiated the acquisition of a mine with iron ore and rare earth minerals deposits valued at over $100 billion, which included resolving over two dozen simultaneous lawsuits in multiple states, Finland, England, and the Channel Islands.
When Mayor Francis Slay appointed him City Counselor of the City of St. Louis in 2014, Calvert became the youngest city attorney in the country, according to the International Association of Municipal Attorneys. In that role, Calvert oversaw 60 staff and a dozen outside law firms representing the city’s departments as well as the St. Louis Development Corporation, the St. Louis Metropolitan Police Department, and St. Louis Lambert International Airport. Calvert’s work as City Counselor included responding to the departure of the St. Louis Rams which led to a $790 million settlement with the National Football League; negotiating legislation creating the state’s first Civilian Oversight Board and first minimum wage ordinance that set a wage rate higher than the state; and negotiating transactions that brought the National Geospatial-Intelligence Agency headquarters to St. Louis. Calvert also authored the Ferguson Commission’s initial charter and strategic plan. At the conclusion of his term as City Counselor, Missouri Lawyer’s Weekly named Calvert the “Law Firm Leader of the Year.”
From 2019 to 2022, Calvert served as Chief of Staff to the County Executive of St. Louis County. As the only direct report to the County Executive, Calvert oversaw all aspects of county government, its budget of almost one billion dollars, over 4,000 employees, and more than 25 departments, boards, commissions, and agencies. Calvert’s leadership included managing all aspects of the COVID-19 pandemic, including crafting policies that protected public health more effectively and produced a faster economic recovery in St. Louis County than any other place in the State of Missouri, according to a Deloitte study. He designed and oversaw the investment of $173 million in federal pandemic aid in less than nine months. And, when a hospital system abruptly withdrew from its role setting up the region’s vaccine distribution infrastructure and left the region empty handed only thre weeks before the vaccine was scheduled to arrive, Calvert gathered a team that successfully built a vaccine distribution system that served over one million residents.
Since leaving government, Calvert served as the Chief Executive Officer of a private family foundation with an endowment of over $360 million. In that role, Calvert developed a new mission and funding priorities, recruited 15 employees to provide critical support to 75 nonprofit grantees and other partners, overhauled the foundation’s accounting functions and internal controls, and in partnership with the Regional Business Council built a talent pipeline for youth in underserved school districts that today serves over 125 young people every weekday after school.
In 2024, Governor Mike Parson appointed Calvert to be a Commissioner of the Bi-State Development Agency of the Missouri-Illinois Metropolitan District. Calvert also currently serves on the board of directors for the Boy Scouts of America's Greater St. Louis Area Council and Heat Up St. Louis Inc. Chief Justice Patricia Breckenridge previously appointed him to serve on the Missouri Supreme Court’s Commission on Racial and Ethnic Fairness.
Calvert is a graduate of Washington University School of Law, where he graduated cum laude and served as the Executive Articles Editor of the Washington University Law Review. A native of rural southern Illinois, he received a Bachelor of Music Performance from Southern Illinois University Carbondale.
As an attorney, Calvert helped solve multidimensional problems clients faced. He has led clients to successful resolutions that required overcoming bet-the-company lawsuits, negotiating multibillion dollar transactions, and navigating media coverage and reputational risks. His work has earned accolades including Missouri Lawyer’s Weekly naming him the “Legal Champion of the Year,” being listed as one of the “Top Bet-the-Company Lawyers in Missouri,” and being named to SuperLawyers several years.
Successful resolutions he engineered include resolving the St. Stanislaus Catholic Church’s dispute with the Archdiocese of St. Louis, a dispute that began in 1888 and resurfaced every decade until its resolution in 2013. The St. Stanislaus experience will be the subject of a forthcoming feature film titled The Faithful, penned by an Emmy-award winning writer and produced by Laurene Powell Jobs. He also negotiated the acquisition of a mine with iron ore and rare earth minerals deposits valued at over $100 billion, which included resolving over two dozen simultaneous lawsuits in multiple states, Finland, England, and the Channel Islands.
When Mayor Francis Slay appointed him City Counselor of the City of St. Louis in 2014, Calvert became the youngest city attorney in the country, according to the International Association of Municipal Attorneys. In that role, Calvert oversaw 60 staff and a dozen outside law firms representing the city’s departments as well as the St. Louis Development Corporation, the St. Louis Metropolitan Police Department, and St. Louis Lambert International Airport. Calvert’s work as City Counselor included responding to the departure of the St. Louis Rams which led to a $790 million settlement with the National Football League; negotiating legislation creating the state’s first Civilian Oversight Board and first minimum wage ordinance that set a wage rate higher than the state; and negotiating transactions that brought the National Geospatial-Intelligence Agency headquarters to St. Louis. Calvert also authored the Ferguson Commission’s initial charter and strategic plan. At the conclusion of his term as City Counselor, Missouri Lawyer’s Weekly named Calvert the “Law Firm Leader of the Year.”
From 2019 to 2022, Calvert served as Chief of Staff to the County Executive of St. Louis County. As the only direct report to the County Executive, Calvert oversaw all aspects of county government, its budget of almost one billion dollars, over 4,000 employees, and more than 25 departments, boards, commissions, and agencies. Calvert’s leadership included managing all aspects of the COVID-19 pandemic, including crafting policies that protected public health more effectively and produced a faster economic recovery in St. Louis County than any other place in the State of Missouri, according to a Deloitte study. He designed and oversaw the investment of $173 million in federal pandemic aid in less than nine months. And, when a hospital system abruptly withdrew from its role setting up the region’s vaccine distribution infrastructure and left the region empty handed only thre weeks before the vaccine was scheduled to arrive, Calvert gathered a team that successfully built a vaccine distribution system that served over one million residents.
Since leaving government, Calvert served as the Chief Executive Officer of a private family foundation with an endowment of over $360 million. In that role, Calvert developed a new mission and funding priorities, recruited 15 employees to provide critical support to 75 nonprofit grantees and other partners, overhauled the foundation’s accounting functions and internal controls, and in partnership with the Regional Business Council built a talent pipeline for youth in underserved school districts that today serves over 125 young people every weekday after school.
In 2024, Governor Mike Parson appointed Calvert to be a Commissioner of the Bi-State Development Agency of the Missouri-Illinois Metropolitan District. Calvert also currently serves on the board of directors for the Boy Scouts of America's Greater St. Louis Area Council and Heat Up St. Louis Inc. Chief Justice Patricia Breckenridge previously appointed him to serve on the Missouri Supreme Court’s Commission on Racial and Ethnic Fairness.
Calvert is a graduate of Washington University School of Law, where he graduated cum laude and served as the Executive Articles Editor of the Washington University Law Review. A native of rural southern Illinois, he received a Bachelor of Music Performance from Southern Illinois University Carbondale.