To avoid the plaintiff double tax trap—where taxes are paid on both the net settlement and the legal fees—plaintiffs should use a Plaintiff Recovery Trust (PRT) to ensure only the net recovery is taxed. This, along with structured settlement annuities, can significantly reduce tax liabilities on taxable awards like punitive damages or emotional distress.
Program Summary. Since the 2018 tax law changes, many plaintiffs have encountered unexpected tax consequences, paying more than necessary on their settlements. With the elimination of legal fee deductions, plaintiffs are now often taxed on both their net recovery and the portion allocated to attorney fees.
To avoid double taxation, one option is to structure the business as a “flow-through” or pass-through entity. In this setup, profits bypass corporate taxation and go directly to the business owners. The owners then report and pay taxes on their share of the income at their respective tax rates.
To avoid double taxation, use "pass-through" business structures like LLCs or S Corporations where profits are taxed only once at the owner's individual rate, instead of C Corporations which are taxed at the corporate level and again on dividends; alternatively, C Corp owners can pay salaries, retain earnings strategically, or use income splitting, while international earners rely on foreign tax credits or treaty provisions.
Start by maximizing deductions like student loan interest and charitable contributions, as well as credits like the Earned Income Tax Credit and Child Tax Credit. Consider investments such as municipal bonds for tax-free interest and capitalize on employer benefits like retirement accounts to reduce taxable income.
To avoid double taxation, use "pass-through" business structures like LLCs or S Corporations where profits are taxed only once at the owner's individual rate, instead of C Corporations which are taxed at the corporate level and again on dividends; alternatively, C Corp owners can pay salaries, retain earnings strategically, or use income splitting, while international earners rely on foreign tax credits or treaty provisions.
On the special type of corporation of interest to small businesses is the Subchapter S corporation. This type of corporation avoids double taxation by having its income taxed to the shareholders as if the corporation were a partnership.
The IRS $600 rule refers to a change in reporting requirements for third-party payment apps (like Venmo, PayPal) for taxable income from goods and services, where platforms must send a Form 1099-K if you receive over $600 in a year, intended to capture gig economy/side hustle income, though delays and phased implementation have adjusted the timeline, with current rules for 2024 using a higher threshold ($5,000) before fully phasing to $600 for future years, but remember all taxable income, regardless of form, must always be reported.
Formalizing a plaintiff recovery trust requires careful drafting of the trust agreement. This document lays out the rules for how and when distributions occur. Attorneys typically work closely with the trustee to create provisions that address the plaintiff's immediate and long-term financial priorities.
To minimize taxes on a lump sum, rollover retirement funds to IRAs/401(k)s to defer taxes, use structured settlements for legal payouts to spread income over years and stay in lower tax brackets, bunch deductions (charitable gifts, real estate taxes) in the year received, and consider if it's best to take smaller distributions or choose Net Unrealized Appreciation (NUA) for company stock, always seeking professional tax advice first.
To avoid double taxation, use "pass-through" business structures like LLCs or S Corporations where profits are taxed only once at the owner's individual rate, instead of C Corporations which are taxed at the corporate level and again on dividends; alternatively, C Corp owners can pay salaries, retain earnings strategically, or use income splitting, while international earners rely on foreign tax credits or treaty provisions.
Treat your settlement like a financial windfall: don't rush spending, and take time to plan carefully before making major purchases or lifestyle changes. Understand how the money is divided: lump sum vs structured payments, and how medical bills, liens, attorney fees, and taxes may reduce your net.
The IRS 7-year rule primarily applies to keeping records for claiming a deduction for bad debts or losses from worthless securities, allowing a longer period to file for a credit or refund, but it's not a universal audit limit; it's often a recommended safe buffer for general record-keeping, with the standard IRS audit period usually being 3 years, extending to 6 years for substantial income omission (over 25%) or foreign income issues, and indefinitely for fraud.
Legal settlements for physical injuries or sickness are generally non-taxable**, including compensation for medical expenses (unless previously deducted), pain and suffering, and related emotional distress, thanks to IRC Section 104(a)(2). Other types, like punitive damages, lost wages, and emotional distress not tied to physical harm, are usually taxable.
The IRS "10k rule" primarily refers to the requirement for businesses and financial institutions to report cash transactions over $10,000 by filing Form 8300 (for businesses) or a Currency Transaction Report (CTR) (for banks), under the Bank Secrecy Act. This rule helps combat money laundering, tax evasion, and terrorist financing, requiring reporting for single transactions or related transactions totaling over $10,000 in cash within a year, with penalties for non-compliance.
The "20k rule" refers to the traditional IRS threshold for reporting income from payment apps and online marketplaces on Form 1099-K: over $20,000 in gross payments AND more than 200 transactions in a calendar year. While a law (the American Rescue Plan) temporarily lowered the threshold to $600, recent legislation, the One Big Beautiful Bill Act (OBBBA) (OBBBA), has reinstated the $20,000/200-transaction rule for tax years starting in 2025, providing relief for casual sellers and gig workers.
Zelle works differently by facilitating transfers directly between banks and does not report payments to the IRS.
To avoid double taxation, use "pass-through" business structures like LLCs or S Corporations where profits are taxed only once at the owner's individual rate, instead of C Corporations which are taxed at the corporate level and again on dividends; alternatively, C Corp owners can pay salaries, retain earnings strategically, or use income splitting, while international earners rely on foreign tax credits or treaty provisions.
DTAA is an agreement signed between India and several countries to ensure that individuals and entities are not taxed twice on the same income. DTAA is especially relevant for a person earning income in one country while being a resident in another country without DTAA; such income could be taxed in both countries.
The most tax-efficient way for many active LLC owners is to elect S-corporation status, paying yourself a "reasonable" W-2 salary subject to payroll taxes, with remaining profits taken as distributions (dividends) not subject to self-employment tax, saving ~15% on the distribution portion. For single-member LLCs or those with lower profits, owner's draws (flexible withdrawals) are simpler but all profits are subject to self-employment tax, while a salary-only approach (default LLC/sole prop) also taxes all net income at full self-employment rates. Always consult a tax professional, as the best method depends on your specific income and business structure.
An S corporation, sometimes called an S corp, is a special type of corporation that's designed to avoid the double taxation drawback of regular C corps. S corps allow profits, and some losses, to be passed through directly to owners' personal income without ever being subject to corporate tax rates.
Foreign Earned Income Exclusion (FEIE)
The FEIE allows you to exclude a significant portion of your foreign earned income from U.S. taxation. For tax year 2025 (filed in 2026), you can exclude up to $130,000. If you're married and both spouses qualify, you can each claim the exclusion for a combined total of $260,000.