14 May Game Changing Tax Strategies: Protecting and Maximizing Wealth for Professional Athletes
Professional athletes financial, legal and advisory teams play a critical role in structuring deals that go far beyond the field. To help navigate the complex tax landscape that comes with major contracts, endorsements, and high-stakes careers, we sat down with Jason Conn, Director of Tax at TSG Tax Management.
When a professional athlete first signs a major contract, what should sports lawyers prioritize from a tax perspective?
The ink is barely dry on a big contract when the real game begins — the tax game. Sports lawyers should prioritize building a strong tax foundation immediately. This means proactive entity structuring, modeling multi-state “jock tax” exposure, and carefully planning how bonuses, incentives, and deferred compensation will be taxed across jurisdictions.
At TSG Tax Management, we specialize in creating game-changing tax strategies tailored to the unique realities of professional sports. Our hands-on, proactive approach helps turn complex tax challenges into opportunities for meaningful savings, so athletes can stay focused on performing at the highest level.
From your perspective, what role does a sports attorney play in an athlete’s long-term tax and financial strategy?
Sports attorneys serve as the quarterback — calling the plays that shape not only the deal but the athlete’s financial future. The legal structure you negotiate directly impacts tax efficiency for years to come.
The most successful outcomes happen when attorneys bring specialized tax experts onto the field early. At TSG Tax, we collaborate closely with legal counsel to optimize compensation structures, minimize unnecessary liabilities, and align tax planning with the athlete’s career trajectory and life goals.
What are the biggest tax challenges you see for athletes and the professional teams they play for?
Athletes operate in a complex arena: multi-state taxation, endorsement and image rights income, short career spans, and ever-changing tax rules. Teams and players must also navigate collective bargaining agreements with significant tax implications.
What sets TSG Tax Management apart is our ability to deliver sophisticated, forward-looking strategies with true concierge-level service. We don’t just handle compliance — we design personalized tax playbooks using advanced planning techniques and entity structuring to reduce liabilities and deliver real financial peace of mind.
How does TSG Tax Management’s approach differ from a traditional accounting firm when working with high-earning athletes and entertainers?
Traditional firms often play defense — focusing primarily on compliance and filing after the fact. At TSG Tax Management, we play offense through proactive, customized tax planning designed around each client’s specific goals and lifestyle.
We deliver a Legacy Lifestyle approach: concierge-level service that simplifies complexity while maximizing savings. Our client-first philosophy, backed by decades of expertise and cutting-edge tools, creates a true partnership that goes well beyond standard tax preparation.
How does TSG Tax Management work with the TSG Sports and Entertainment team to support athletes?
In professional sports, winning requires an all-star team working in perfect sync. That’s exactly how we operate at TSG. We closely coordinate with the TSG Sports and Entertainment team — as well as wealth management and legal advisors — to ensure every aspect of the athlete’s advisory ecosystem is aligned.
This integrated approach eliminates silos, prevents conflicting advice, and creates powerful, game-changing outcomes — whether we’re modeling after-tax contract scenarios, structuring endorsement deals, or planning for life after the final whistle.
If you could give one piece of advice to sports lawyers representing professional athletes and teams, what would it be?
Bring specialized tax expertise into the huddle as early as possible — ideally during contract negotiations. The structural decisions made early in the process can have an outsized impact on an athlete’s net worth and long-term security.
Partner with a team that truly understands both the fast-paced world of professional sports and sophisticated tax strategy. At TSG Tax Management, we’re committed to being that proactive, trusted partner — delivering personalized, game-changing tax strategies with the concierge-level service elite athletes and their legal teams deserve. When the right players move together, everyone wins.
Learn more about how TSG Tax can help you or your client at TSGTM.com/services or contact us to start the conversation today!