Structured Settlements 4Real®Blog 2026

Structured settlements expert John Darer reviews the latest structured settlements and settlement planning information and news, and provides expert opinion and highly regarded commentary. that is spicy, Informative, irreverent and effective for over 20 years.

Gobler’s “Should You Cash Out a Structured Settlement” is a Turkey

by Structured Settlement Watchdog

On July 19, 2023, the New York Post ran a Personal Finance article by freelance writer Erin Gobler, citing a source ironically called “Credible.” The Post notes it earns a commission if readers click the link and finalize a loan through Credible.

An award is not a structured settlement

“Gobbler” to “Gobler”

In a case of you lost it at hello, Gobler writes

“If you’re the plaintiff in a personal injury or similar claim and win your case, you could find yourself awarded a large amount of cash. But you may not necessarily get that money in one lump sum. Instead, monetary awards may be disbursed over a longer period in what’s known as a structured settlement” says Gobler.

  1. An Award is not a Settlement
  2. A Settlement is not an award. That’s why it’s called a settlement. Pretty basic stuff.
  3. A monetary award, would not be disbursed as a structured settlement.
  4. A settlement is a negotiated compromise. This is key. You don’t need to “win your case” to enter into a structured settlement with your adversary or their insurance company.
  5. In New York, there are a pair of periodic payment of judgments statutes that provide for portions of a judgment in excess of certain thresholds to be paid by what is known as a structured judgment. The statutes are described at New York CPLR 5031-5039 for recovery of damages due to Medical, Dental and Podiatric malpractice (known as Article “50-A”) and CPLR 5041-5049 to recover damages for personal injury, injury to property or wrongful death, not subject to Article 50-A  (known as Article “50-B”)
  6. As long as there are good faith appealable issues and the parties have a meeting of the minds, they can enter into a settlement in lieu of judgment. 

Gobler  “A structured settlement can provide a source of tax-free income over a long period. But for someone who needs the money right away — perhaps due to the injury that landed them in court in the first place — cashing out the structured settlement could be an option. However, it’s important to consider the benefits and downsides beforehand”.

  1. Work with a credentialed and experienced settlement planner to explore your options before signing any release. What is Settlement Planning? Settlement Advisors and Transitional Financial Planning NY|NYC|CT|NJ (4structures.com)
  2. A structured settlement can provide tax free income over short term, intermediate term and long term time frames. 
  3. Periodic payment settlements can be used in the comprise of claims for damages that are taxable. What are Non Qualified Structured Settlements and Non Qualified Assignments for Tax Deferral (4structures.com)
  4. Muliple income streams can be customized in the same annuity contract, or in multiple contracts, diversified by company if desired or prudent. What Are Structured Settlement Annuities? Structured Settlements FAQ (4structures.com)
  5. Don’t enter into a structured settlement if your mind is on “cashing out” in the near term.

Last updated February 2, 2026

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