Who Should I Hire First After Winning the Lottery?
Last reviewed: July 2026
Hire a lawyer first. After winning the lottery, your very first call should be to an estate planning and asset protection attorney, before you claim the prize, before you tell anyone, and before any money hits your account. A lottery financial advisor comes third, after the lawyer and a CPA, because the attorney sets up the legal structures that protect your winnings and the CPA models the tax hit. Build the team in that order and you avoid the mistakes that drain windfalls fast.
Key Takeaways
- Hire an estate attorney first, a CPA second, and a lottery financial advisor third, in that exact order.
- The IRS requires 24% federal withholding on lottery prizes over $5,000, but the real bill can hit the top 37% bracket.
- Claiming through a trust or LLC can protect your anonymity and your assets, but only in states that allow it.
- Interview at least three professionals for each role and avoid anyone selling products on commission.
About the Author: Jeff Judge, CFP®, AEP®, ChFC®, CLU® is Managing Partner of Chesapeake Financial Planners in Forest Hill, Maryland. He has been helping families and business owners across Harford County and the Baltimore metro area navigate sudden wealth events since earning his CFP® certification in 2013, by using Chesapeake Financial Planners’ signature process, the R.U.D.D.E.R. method™. Jeff has watched windfall recipients lose more to rushed decisions in the first ninety days than they ever lose to bad investments, which is exactly why the order you hire people in matters so much.
Why You Can't Handle a Lottery Win Alone
A lottery win creates a level of financial complexity that even sophisticated people have never faced. You are suddenly dealing with state and federal taxes that can claim a large share of the prize, asset protection needs to shield you from lawsuits and creditors, investment decisions that determine whether the money lasts a decade or a lifetime, and privacy risks that can put your family at real danger.
No single professional covers all of that. A lawyer is not a tax modeler. A CPA does not build investment portfolios. A financial advisor does not draft trusts. You need a coordinated team, and you need it assembled before you walk in to claim the prize. The size of the stakes is real: recent Powerball jackpots have exceeded $1 billion, and even a smaller multi-million-dollar prize is enough to attract bad actors and bad advice.
This is also where a structured process earns its keep. At Chesapeake Financial Planners, we run sudden-money clients through the R.U.D.D.E.R. Method™, our six-step planning process: Review and Recognize, Uncover and Understand, Design and Develop, Discuss and Decide, Execute and Empower, and Reassess and Refine. It keeps emotion from driving million-dollar decisions in the first frantic weeks.
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Why You Hire a Lawyer First After Winning the Lottery
Your first hire is an attorney who specializes in estate planning, asset protection, and ideally sudden wealth or lottery cases. The lawyer comes first for four concrete reasons.
They help you claim the prize strategically. Depending on your state, you may be able to claim through a trust or LLC to protect your anonymity. Your attorney knows the rules and structures the claim correctly before the deadline, which is usually fixed and unforgiving.
They put legal protections in place immediately. Trusts, LLCs, and related entities shield your assets from lawsuits, creditors, and family disputes. These structures need to exist before the money lands, not after a problem appears.
They coordinate the rest of your team. A strong attorney helps you vet and hire your CPA, your lottery financial advisor, and your insurance professional, then keeps everyone rowing in the same direction.
They protect you from your own first impulses. In the emotional chaos of winning, the lawyer is the person who can say "let's slow down" when you are about to wire money to a relative or buy three houses in a week.
Do not hire the first attorney who says they can help. Interview at least three. Look for experience with high-net-worth clients, knowledge of your state's claiming rules, no conflicts of interest, a transparent flat or hourly fee structure, and strong references from similar clients.
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Why You Hire a CPA Second for Lottery Tax Planning
Once your attorney is in place, bring in a CPA or tax professional who handles complex, high-net-worth situations. Lottery tax planning is where winners quietly lose enormous sums, because the headline number is never the number you keep.
The IRS treats lottery winnings as ordinary income and requires 24% federal withholding on prizes over $5,000. That withholding is not your final bill. A large jackpot pushes you into the top federal income tax bracket of 37%, and most states layer their own income tax on top. Your CPA models lump sum versus annuity, shows the tax consequences of each, and builds a strategy for that first brutal tax year.
A good tax professional also advises on charitable giving, where timing and structure can save serious money, and coordinates with your advisor so your investments stay tax-efficient. Look for experience with high-income clients, knowledge of multi-state issues if you plan to move, a proactive planning approach rather than return preparation, and no product sales on the side.
Jeff Judge often points out that the lump-sum-versus-annuity decision is rarely about the math alone. It is about discipline. He has seen clients who would have been far better protected by the annuity simply because it removed the temptation to spend the whole prize at once.
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Why the Lottery Financial Advisor Comes Third
With legal and tax guidance in place, you hire a financial advisor to invest, manage, and protect the wealth for the long term. The advisor comes third on purpose: their work depends on the structures the attorney built and the tax framework the CPA created.
Your advisor builds a diversified portfolio designed to generate income, preserve capital, and grow over time. Just as important, they create a sustainable spending plan. Having $10 million does not mean you can spend $10 million; a disciplined withdrawal rate is what keeps the money working for decades instead of disappearing in a few years. The advisor also stress-tests the plan against inflation, market downturns, and the lifestyle changes that almost always follow a windfall.
Choose a fee-based fiduciary who is legally obligated to act in your interest, not a salesperson earning commission on the products they recommend. That single distinction protects you from the most common form of windfall erosion.
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Frequently Asked Questions
Should I hire a lawyer or financial advisor first after winning the lottery?
Hire the lawyer first. The attorney structures how you claim the prize, sets up trusts or LLCs to protect your anonymity and assets, and coordinates the rest of your team. A lottery financial advisor comes third, after the lawyer and CPA, because investment decisions depend on the legal and tax framework already being in place.
How much tax will I pay on lottery winnings?
The IRS requires 24% federal withholding on lottery prizes over $5,000, but that is only an upfront deposit. A large jackpot pushes you into the top federal bracket of 37%, and most states add their own income tax. Your actual combined bill can approach or exceed 40% depending on where you live.
Can I stay anonymous after winning the lottery?
It depends entirely on your state. Some states let you claim through a trust or LLC to shield your name from public records, while others publish winners' identities by law. This is exactly why you hire an attorney before claiming, since the structure must be set up before you submit the ticket, not after.
Should I take the lump sum or the annuity?
There is no universal right answer; it depends on your tax situation, discipline, and goals. A CPA models both options and shows the after-tax outcome of each. The annuity spreads the tax hit and limits the temptation to overspend, while the lump sum gives you full control and investment flexibility from day one.
What kind of financial advisor should a lottery winner hire?
Hire a fee-based fiduciary who is legally required to act in your interest, not a commissioned salesperson. Look for direct experience with sudden wealth and high-net-worth clients, a transparent fee structure, and references from comparable situations. The advisor builds your investment strategy and a sustainable spending plan that makes the money last for decades.
What to Do This Week
Before you claim a single dollar, decide on your order of operations: attorney first, CPA second, lottery financial advisor third. That sequence protects your privacy, controls your tax exposure, and keeps your decisions from being driven by emotion. If you want a clear framework for building your team and avoiding the traps that catch most winners, our sudden wealth planning guide walks through every step in detail. Download it at chesapeakefp.com.
Disclosures
The information provided is for educational purposes only and should not be construed as investment advice. Investment strategies should be tailored to individual circumstances, risk tolerance, and goals. Past performance doesn't guarantee future results. Consult with qualified financial professionals regarding your specific situation.
Advisors associated with Chesapeake Financial Planners may be either (1) LPL Financial Registered Representatives offering securities through LPL Financial, Member FINRA and SIPC, and investment advisor representatives offering investment advice through Great Valley Advisor Group; or (2) solely investment advisor representatives offering investment advice through Great Valley Advisor Group and not affiliated with LPL Financial. Great Valley Advisor Group, and Chesapeake Financial Planners are separate entities from LPL Financial.
