8 min read
Office Lottery Pool Won? How to Split a Jackpot Right
How office lottery pools split a Powerball or Mega Millions jackpot: Form 5754, what each share keeps after tax, gift-tax traps and real pool lawsuits.
Guides and stories
The Jackpot Dreaming Blog
Plain-English guides for jackpot winners and dreamers: taxes, lump sum vs. annuity, privacy, trusts, and what to do first.
7 min read
The $1.35B Lottery Winner Who Lost His Privacy Fight
Maine's $1.35B Mega Millions winner sued his ex over an NDA, then learned that courts don't do secrecy. What the Sept. 2026 ruling teaches big winners.
7 min read
What Really Happens to Lottery Winners? Stories and Data
Real stories of jackpot winners who thrived and who struggled, what research says about winners' lives, and why the '70% go broke' stat is unsupported.
7 min read
Should Lottery Winners Buy Whole Life Insurance?
A skeptical guide for big winners: when permanent life insurance makes sense in 2026 (estate tax over $15M, ILITs), what it costs, and what to ask an agent.
8 min read
How Lottery Winners Use Trusts to Stay Private
Which states let jackpot winners stay anonymous, how blind and dynasty trusts work, 2026 gift and estate tax limits, and what to do in your first 30 days.