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.

by Structured Settlement Watchdog

Since October 2016, the Rhode Island case has been stirring up chatter, involving an AnnuitySold email that sneakily delivered documents in a fraudulent lawsuit to a process server, all in a dubious attempt to pull a fast one on the Rhode Island judge and Google

While the con initially worked, some sharp legal work recently resulted in a financial reverse for Annuity Sold's Richart Ruddie.

Which brings up the Pros and Cons of Selling a Structured Settlement For Cash, an article on their website that raises the issue about whether Annuity Sold Pros Are Really Cons.

AnnuitySold Claims

It gives you the opportunity to make an investment that can double, triple, or even quadruple in the future.

Why AnnuitySold Pro is a Con

You sell structured settlement payment rights at a high cost.  Would you give up your "steady job" for something that is speculative?  

AnnuitySold Claims

Being able to hold all of the money from your settlement at one time allows you to explore more options for your life than if you had to wait every month/year to receive the money in small amounts

Why AnnuitySold Pro is a Con

  • Annuity Sold is soliciting you to sell your steady payments to them so that THEY can receive the money in small amounts.  That is an AnnuitySold con. 
  • The other con is that if you sell your structured settlement payment rights to Annuity Sold you will not receive all of the money because Annuity Sold is taking a haircut. In fact if you sell structured settlement payments to any settlement purchaser you will NEVER get all of your money.

AnnuitySold Not Credible Source of Structured Settlement Information

Annuity Sold claims that having a structure "allows you to take advantage of the tax benefit that comes with having a lower income than if you were to collect all the money at once and have your income for the year in which you received it go up"  "However, studies show that these tax benefits don’t end up saving you that much if you are a senior by the time your payments stop coming in because senior citizens receive many tax exemptions already"

Why AnnuitySold is full of it

Despite Annuity Sold's "obsession with size", the tax benefits that inure to structured settlements have nothing to do with size.  A structured settlement is a way to pay for legal damages. There are laws concerning the taxation of damages.  For example, where damages represent payments as compensation for personal physical injury or physical sickness there is an exemption under IRC 104(a)(2).

Where are these elusive studies that AnnuitySold mentions? It’s been agreed for ages that the number one fear of seniors isn’t heights or spiders—it’s running out of money!

Consider these sources:

Older Americans Are More Afraid of Running out of Money Than Death  Motley Fool September 25, 2016

  • Transamerica study 43% of those 50 and older
  • American Institute of CPAs 57% of financial planners said about their clients
  • Allianz study 60% of Baby Boomers

Americans' Biggest Fear: Running Out of Money Journal of Accountancy October 6, 2016

Senior Citizens Lose Billions , Fear to Report Financial Exploitation    June 15, 2016  USA Today

 

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