Taxes for bettors & traders, in plain English.
Short, no-nonsense guides to the forms and rules that actually matter — and how to keep them straight.
Glossary — 56 terms, defined Gross winnings vs profit, every form, and the code sections behind them. Open →The IRS said I owed $9,141. Most of it wasn't tax on my winnings.
A CP2000 for 2023 arrived this March. Fifty-seven percent of the proposed balance was self-employment tax on contest winnings that were never a business — plus the letter that cut it to about $4,800.
Read guide →Your first $17,889 of losses buys you nothing
Losses are an itemized deduction. Clear the standard deduction or you deduct zero — and a break-even year gets taxed on every dollar of gross winnings.
Read guide →April 15 isn't your deadline. It's one of four.
Betting profit arrives with no withholding. A February score was due in April — of that same year. The four dates, the two safe harbors, and the lever that fixes a missed quarter.
Read guide →Why your contest site sends a 1099 and your sportsbook sends nothing
You can win $400,000 on sports and never get a single form. Two different reporting regimes — and why that means the records have to come from you.
Read guide →There's no such thing as a semi-pro gambler
Professional status can save $8,984 in Wisconsin and cost $4,098 in California — same bettor, same bets. What it really takes to qualify, and why claiming it wrongly is so costly.
Read guide →You broke even. You still owe $2,400.
Since January 2026 you can deduct only 90% of gambling losses. You can finish the year down $19,000 and still owe federal tax — and it scales with volume, not profit.
Read guide →Ten states where losing money still costs you tax
These states tax gross gambling winnings and allow no loss deduction at all. A break-even bettor in Connecticut owes $6,990 on zero profit — here's the list and the math.
Read guide →The 1099 rule just changed: $600 → $2,000
Contest and sweepstakes sites now only file a 1099 once you clear $2,000 with them for the year. Fewer forms — and one aggregate-rule trap that catches people.
Read guide →Three ways to file your prediction-market trades
Kalshi gains can be reported as ordinary income, capital gain, or under §1256 — worth up to $10,200 on a $100k gain. The forms, the mechanics, and the case for each.
Read guide →A W-2G isn't your year-end profit statement
What a W-2G actually is, when a single bet triggers one, and the 2026 change that raised the threshold from $600 to $2,000.
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