Short version: The IRS splits the year into four payment periods of three, two, three and four months, and the next 2026 payment is due January 15, 2027. When a deal pays all at once, the regular method still asks for four equal payments, and the annualized method lets each one follow the money.
A deal pays you the whole amount. Nobody takes tax out first. That's the difference between a deal and a paycheck, and it's why the IRS has a second way to collect: estimated tax, paid by you during the year with Form 1040-ES.
Leave's taxes page covers who pays it and the four dates. This post is about what happens when the money doesn't arrive evenly, which for most deals is the whole story. One deal, one payment, one date.
Why the IRS wants it during the year
Publication 505 opens with the rule: "The federal income tax is a pay-as-you-go tax." An employee pays as they go through withholding. People in business for themselves, the publication says, "will generally have to pay their tax this way," through estimated tax.
The IRS's Taxpayer Advocate Service says student-athletes paid for their name are regarded as self-employed. Self-employment tax is 15.3 percent, 12.4 for Social Security and 2.9 for Medicare, once net earnings reach $400 in a year. Estimated payments cover it along with income tax.
In most cases, the 2026 Form 1040-ES says, you have to pay estimated tax for 2026 if you expect to owe at least $1,000 after withholding and refundable credits, and your withholding and credits will come in under the smaller of two amounts:
- 90 percent of the tax on your 2026 return, or
- 100 percent of the tax on your 2025 return.
If your adjusted gross income for 2025 was more than $150,000, or $75,000 if you're married filing separately, the 100 becomes 110. Adjusted gross income, or AGI, is the income figure on the return before the standard deduction comes off.
One exception covers a lot of first deals. If you were a U.S. citizen or resident alien for all of 2025 and had no tax liability for 2025, the form says you don't have to pay estimated tax for 2026.
The tax on the deal is still owed. It's paid with the return.
Quarterly, sort of
They're called quarterly payments. The periods aren't quarters. This is the 2026 schedule as the IRS publishes it:
| Income earned | Payment due |
|---|---|
| January 1 to March 31, 2026 | April 15, 2026 |
| April 1 to May 31, 2026 | June 15, 2026 |
| June 1 to August 31, 2026 | September 15, 2026 |
| September 1 to December 31, 2026 | January 15, 2027 |
A due date that falls on a Saturday, Sunday or legal holiday moves to the next business day.
The next one is January 15, 2027, for income from September 1 through December 31. The form adds a way around that one: you don't have to make it if you file your 2026 return by February 1, 2027 and pay the entire balance with it.
They're called quarterly. The periods run three months, then two, then three, then four.
When a deal pays all at once
The regular method in Publication 505 takes the year's estimated tax and divides it by four. The publication says to use it "only if your income is basically the same throughout the year." A deal that pays once usually isn't that.
Say a deal pays $20,000 on November 10, 2026. Under the regular method, a quarter of the year's required payment was due back on April 15, months before the deal existed. If that quarter went unpaid, the penalty for that period counts from April 15.
The IRS has a second method for this: the annualized income installment method. Form 1040-ES describes it for people who receive income "unevenly throughout the year." Chapter 2 of Publication 505 walks through it.
It looks at your income from January 1 to the end of each period, March 31, May 31, August 31 and December 31, and figures what was due by each date from what you'd actually earned by then. Money that arrives in November counts in the last period.
The 2026 form names one case directly. If after March 31, 2026 a large change in income means you have to start making estimated payments, it points to the annualized method, with Form 2210 and its Schedule AI filed with the return "even if no penalty is owed."
So two athletes with the same $20,000 can have different payment schedules. One was paid in February. One was paid in November. The year's tax can come out the same. The due dates don't.
How the penalty works
Paying too little for a period can bring a penalty, figured on Form 2210. The 2026 Form 1040-ES says it's charged on each underpayment "for the number of days it remains unpaid." It runs by the day, period by period.
Two details catch people. Publication 505 says the penalty can apply "even if you are due a refund when you file your tax return." And under the Form 2210 instructions, a payment goes first to the oldest unpaid period, even if you mark it for a later one.
The IRS's estimated taxes page lists who generally avoids it: anyone who owes less than $1,000 after withholding and credits, or who paid at least 90 percent of this year's tax or 100 percent of last year's, whichever is smaller.
For higher incomes, that last figure is the 110 percent above.
With a paycheck on the side
Wages change the picture a little. Form 1040-ES says someone with wages may be able to cover other income by asking the employer to take more tax out of each paycheck, with a new Form W-4.
Withholding is also counted differently. Under the Form 2210 instructions, federal income tax withheld counts as paid one-fourth on each payment due date, unless you show otherwise. An estimated payment counts when it's made.
How a payment is made
The 2026 Form 1040-ES lists the ways. Your IRS Online Account. IRS Direct Pay, straight from a checking or savings account "at no cost to you." EFTPS, also free once you're enrolled. A debit or credit card, where the processor charges a fee. Or a check with a payment voucher.
A mailed payment counts on its postmark date. The form adds a caution: the postmark is the date a postal facility processes it, which may not be the day it went in the mailbox.
You can also make more than four payments. The form says so, as long as what you pay in each period adds up to what was due by that period's date.
This post covers federal tax only. A state with an income tax has its own rules.
The numbers that apply to you depend on the rest of your year: other income, deductions, and what you owed last year. Every source is linked at the bottom of the post.
What Leave does with this
Upload a contract and Leave reads it back in plain words, and its dates go on Home. Leave doesn't figure or file taxes.
It takes 0 percent of any deal, so what the deal pays is yours, and so is the tax on it. You decide how you handle it.
Questions people ask
When is the next estimated tax payment due?
For income earned September 1 through December 31, 2026, it's due January 15, 2027, per the 2026 Form 1040-ES. That payment can be skipped if the 2026 return is filed by February 1, 2027 and the whole balance is paid with it.
If a deal pays all at once, are the four payments still equal?
Under the regular method, yes. Each one is a quarter of the year's required payment. The annualized income installment method, in chapter 2 of Publication 505 and on Schedule AI of Form 2210, figures each payment from the income actually earned by then.
Can there be a penalty even with a refund coming?
Yes. Publication 505 says a penalty for a payment period can apply even if a refund is due when the return is filed. It's figured period by period, for the number of days each underpayment stays unpaid.
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