Succession was part of Rich Naski’s work before it became part of his job description. He had advised families and their businesses on the arrangements that carry ownership and authority into the future. In April 2024, he became chief executive of Duchossois Capital Management, a Chicago investment firm with a family business behind it and a generational transition underway.
There is a pleasing symmetry here. The lawyer who worked on continuity now has responsibility for an organization living through it. The chronology gives this career its shape: joining the Duchossois organization in 2016, serving as head of its family office, becoming chief operating officer in 2023, then moving into the CEO role the following April.
Before the corner office, the fine print
Naski’s earlier work belonged to the legal world. He was a partner at Winston & Strawn in Chicago, then a member at Bodman in Detroit. His practice covered tax and estate planning, corporate governance, succession, private trust company formation and charitable planning. These are the subjects that give a family enterprise its legal architecture.
A business can have a splendid balance sheet and still need an answer to the question of who gets to make the next decision. Succession planning brings that question forward. Governance puts responsibilities into a form people can use. The vocabulary may be dry; the consequences rarely are.
His education took place at the University of Michigan, where he earned a bachelor’s degree and, at its law school, a J.D. cum laude. The legal career that followed put families and their businesses at the center of his professional work. His later move into the Duchossois organization carried that subject into an executive setting.
- 2016Joins the Duchossois organization
- 2023Named chief operating officer
- April 2024Assumes the chief executive role
A new chief executive, a new chair
The 2024 change involved two seats. Naski succeeded Michael Flannery as CEO. Ashley D. Joyce, Craig Duchossois’s daughter, became chair. Flannery remains a senior advisor; Craig is chair emeritus. The transition brought a family leadership change and an operating leadership change into the same chapter.
DCM had been launched in 2013 by The Duchossois Group to give its investment activity a more formal structure. Flannery was named president at its creation. His own earlier career also included law, followed by financial and operating responsibilities within the Duchossois organization.
For Naski, the move to CEO followed years inside the organization. It is a progression from serving the family office to overseeing the firm. That sequence matters more than any dramatic description of the appointment: the successive roles are the story.
A family business has to make room for the next decision-maker.On continuity and the work of succession
The family behind the investment firm
The setting for Naski’s appointment was already changing. In March 2024, Craig Duchossois described the family’s move from a hands-on holding company toward a diversified investment company. He had raised the succession question with his siblings years earlier, recognizing the demands that operating businesses would place on the next generation.
He also drew a practical distinction between helping shareholders and taking over their decisions. The family office reviewed individual financial statements and provided guidance. Responsibility stayed with the shareholder. Even applying for a mortgage could become an occasion for an introduction and a lesson, rather than an errand handed off to staff.
That gives a specific institutional context to Naski’s former role as head of the family office. Advice and ownership sit close together here, but they carry different responsibilities. A family office can help people understand a decision while leaving them to make it.
The governance arrangement has equal numbers of family and outside directors: four of each. Joyce’s chair role places family leadership alongside a professional chief executive. The structure gives the succession a form beyond the announcement.
Four places for capital to go
The business Naski now oversees invests across private capital, real estate, funds and public securities. DCM describes a permanent capital base and a flexible holding period. Those characteristics provide the setting for its emphasis on long-term value creation.
Its published private capital criteria favor North American platform businesses. Real estate investments also focus on North America, while the fund mandate is global. The firm’s operating background includes industrial products, transportation, distribution, consumer durables and access control.
Naski’s remit extends across the organization. He also sits on its investment committee and serves as chairman and CEO of Travers Trust Company LLC. Beyond DCM, he is an independent member of the investment and distribution committee for another family’s private trust company, and belongs to the Economic Club of Chicago.
The thread running through these roles is a professional relationship with family capital and the structures around it. The lawyer’s earlier subjects remain recognizable: authority, continuity, ownership and the decisions that follow. At DCM, Naski now carries those responsibilities into the chief executive’s office.