Robert W. Wood

Robert W. Wood

Senior Contributor|Taxes

Robert W. Wood is a tax lawyer (www.WoodLLP.com) who handles tax disputes, writes tax opinions, advises on crypto, disclosures and more.  He is best known for advising plaintiffs on the tax treatment of lawsuit settlements and legal fees, serves as an expert witness, and writes widely for tax publications on these and other tax topics.  You can reach him or his archive of tax articles at Wood@WoodLLP.com.

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Feb 27, 2026

How IRS Taxes Defamation Legal Settlements

Suits for damage to reputation can be about personal reputation, professional reputation or both, with legitimate opportunities for capital gain tax treatment.

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Feb 20, 2026

Giving Back Pay Is Hard, Getting Taxes Back Is Even Harder

IRS does not allow undoing a prior transaction as if it never occurred. You cannot amend your prior year tax return to account for a later event either.

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Feb 19, 2026

IRS Forms 1099-NEC And 1099-MISC Trigger Different Taxes

Form 1099-MISC is for miscellaneous income. But Form 1099-NEC is for payments to independent contractors and adds self-employment tax.

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Feb 18, 2026

Even California Non-Residents Can Face California Taxes

Income from California real estate is always California-source income. Income from tangible property is California-source income if it was physically located in California.

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Feb 6, 2026

How Qualified Settlement Funds For Lawsuits Defer Taxes

QSFs allows plaintiffs time to evaluate structured settlements without involving the defendant. and to delay income tax effects until funds are disbursed.

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Feb 2, 2026

Error On Your IRS Form 1099? What To Do Before You File Taxes

You can approach the issuer and ask the issuer to reissue it correctly. If the issuer of the Form 1099 has already sent it to the IRS, ask for a “corrected” Form 1099.

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Jan 27, 2026

Leaving California Taxes Behind Is Tricky, & Not Just For Billionaires

If you spend more than 9 months in California, you are presumed to be a resident. If you spend 6 months or less, you might qualify as a seasonal visitor.

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Jan 26, 2026

Lawsuit Settlement Form 1099 Requires Special Care On Your Taxes

Many settlement agreements don't say anything about tax forms. Yet many defendants issue a Form 1099 to the plaintiff, and a Form 1099 to the lawyer, often each for 100%.

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Jan 16, 2026

California Is #1 State People Leave—But Tax Man May Follow Them

If you aren’t careful, you can end up with an audit from California’s tough Franchise Tax Board (FTB). Some people who exit still get tax bills and end up in an audit.

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Jan 5, 2026

If George Clooney Gives Up U.S. Citizenship, He’d Face Big IRS Exit Tax

American citizens living abroad still must file U.S tax returns and pay taxes. Giving up citizenship triggers IRS Exit Tax, which in George Clooney's case would be big.