Legacy Law Blog

The Chicago Bears are a charter franchise of the National Football League (NFL). Founded on Sept. 20, 1919, it is one of two remaining charter franchises from the formation of the NFL in 1920.

Since inception, the Bears have been owned by NFL legend George Halas and his heirs. Virginia Halas McCaskey inherited ownership of the Bears from her father in 1983 and continued the legacy as the principal owner of the Bears until her death on Feb. 6.

McCaskey’s death raises significant estate law considerations, particularly given her role as the matriarch of a family-owned NFL franchise. These considerations primarily revolved around succession planning, estate taxes and family governance. These issues were significant given her ownership stake in a high-value asset like an NFL team and the complexities of transferring such wealth across generations.

Below is an exploration of the key estate law implications stemming from her passing.

Estate Planning for Family-Owned Businesses – The Chicago Bears

McCaskey inherited her majority stake in the Chicago Bears from her father, George Halas, and held approximately 80% of the team's ownership which is currently valued at over $6 billion. This makes her estate a prime example of the complexities involved in transferring ownership of a high-value family business to the next generation.

As co-executor with A. Gerson Miller, McCaskey played a key role in ensuring that the Bears remained under family control. The estate underwent a corporate reorganization that allowed Halas Sr. and McCaskey to "freeze" the value of their estates for tax purposes. This strategy benefited her 21 grandchildren and nine surviving children by minimizing estate tax liabilities and preserving family ownership of the Bears. 

Succession planning was a key consideration in the drafting of her estate to ensure the team remained within the family after her death.

• NFL Succession Rules: The NFL requires teams to have clear succession plans to ensure continuity of ownership. For a family to maintain control of a team, at least 30% of ownership must be consolidated under one individual or branch. This likely required careful planning within the McCaskey family to designate successors and avoid disruptions.
• Family Ownership Structure: McCaskey's 80% ownership stake was expected to be divided among her nine surviving children. This division raised questions about how decision-making authority would be managed and whether any family members might consolidate control or sell their shares.

• Succession Planning: McCaskey's death triggers the implementation of a long-prepared succession plan. This division of her ownership stake ensures continuity within the family but also introduces potential challenges, such as disagreements over management and decision-making authority. Clear governance structures and defined roles among heirs would be crucial to maintaining harmony and operational stability within the franchise.

Avoiding Estate Tax Pitfalls

One of the most significant estate law considerations for high-net-worth individuals like McCaskey is minimizing estate taxes. Federal estate tax laws impose a 40% tax on estates exceeding the exemption threshold (currently $12.92 million per individual in 2025). Without proper planning, this could result in a tax bill exceeding $1 billion for an asset like the Bears. However, it appears that McCaskey's estate was structured to minimize these tax liabilities through tools like trusts and strategic gifting during her lifetime.

• Use of Trusts: The McCaskey family likely utilized trusts or other legal mechanisms to reduce estate tax burdens. Certain types of trusts can "freeze" asset values, ensuring that any appreciation in value does not increase tax liabilities for heirs.

• Avoiding Forced Sales: Without proper planning, heirs could face liquidity issues and be forced to sell parts of their inheritance, such as shares in the team, to cover taxes. The McCaskeys appear to have structured their estate plan to prevent this outcome.

Key Strategies Likely Used

To achieve the goal of keeping the Chicago Bears within the McCaskey family, the following estate planning concepts were likely used:

• Irrevocable Trusts: Transferring ownership stakes into irrevocable trusts offer several tax advantages for the giver and the receiver. Irrevocable trusts reduce estate tax exposure, can provide asset protection and can "freeze" asset values for tax purposes while allowing appreciation to occur outside the taxable estate.
• Gifting Strategies: Lifetime transfers of fractional ownership interests to heirs can reduce the taxable estate while taking advantage of discounts, annual gift tax exclusions and lifetime exemptions.
• Buy-Sell Agreements: These agreements can ensure liquidity for heirs to pay taxes without forcing a sale of the team.

Preserving Family Legacy

Beyond financial considerations, McCaskey's death underscores the importance of preserving the legacy and values associated with family-owned businesses. Open communication among heirs and ongoing involvement in governance are critical to avoiding disputes that could jeopardize family unity or lead to a forced sale of the franchise.

Conclusion

McCaskey’s passing highlights how comprehensive estate planning is essential for ensuring smooth transitions in family-owned businesses—particularly those as valuable and complex as an NFL franchise. Her case demonstrates the importance of addressing tax efficiency, succession planning and family governance well in advance.