How To Invest In Structured Settlements

How To Invest In Structured Settlements

Structured settlements are financial arrangements often seen in personal injury, wrongful death, other legal cases, or lottery payouts. 

Instead of a single lump sum payment, the party responsible – typically their insurance company – agrees to make periodic payments to the injured party or plaintiff over time. These payments may span several years or even the plaintiff’s lifetime.

The origination of structured settlements usually comes as an alternative to a larger one-time payment. This approach is taken for a few reasons: it provides long-term financial security for the injured party, mitigates the risk of rapidly depleting a lump sum, and occasionally offers tax advantages.

In most scenarios, the defendant or their insurance company will purchase an annuity from a life insurance company. This annuity acts as a guarantee for regular payments to the plaintiff over a specified period. In many jurisdictions, the original recipient of the structured settlement can sell their future payment rights to a third party or investors if they require a lump sum of money immediately. 

Structured settlement arrangements can also be established for lottery ticket winners.

Americans spend more than $70 billion annually on lottery tickets – and around 1,500 people each year become the lucky individuals who win more than a million dollars.

The lottery winnings can be issued in the form of an annuity. This means the winner takes payments instead of taking a lump sum immediately. Lottery winners can then choose to sell those payments, transforming the winnings back into a lump sum. The investors provide the lump sum to the lottery winner and buy the right to the lifetime payments.

Investing in structured settlements typically involves factoring companies. These companies specialize in purchasing structured settlements and future payments from the original recipients for a discounted lump sum. Individual investors may buy structured settlements directly, but investing in pools or funds with a diversified portfolio of structured settlements is more typical. This diversification helps spread the risk across multiple settlements.

The yield or return for the investor is the difference between the discounted amount they paid for the structured settlement and the total future payments they’ll receive. Investing in structured settlements provides a unique and potentially profitable opportunity. 

Why Invest In Structured Settlements?

Investing in structured settlements has become attractive for investors for various reasons, and it’s easy to see why. One of the primary draws is the prospect of steady returns. By acquiring the rights to structured settlements, investors can enjoy a regular and predictable stream of cashflow over time.

Another appealing aspect is the opportunity to buy at a discount. Investors typically purchase these settlements at a price lower than their future value, aiming for a specific return on investment.

Structured settlements are mainly independent of the stock or bond markets’ ebb and flow. This characteristic can help diversify an investor’s portfolio.

Finally, there is an element of perceived safety that attracts many investors. The annuities that back structured settlements are often purchased from highly rated-insurance companies. 

The Structured Settlement Ecosystem

Structured settlements inhabit a unique space at the crossroads of the legal and financial sectors. 

Important players are insurance companies, often representing the defendant, stepping up to make these settlement payments. They usually buy annuities to guarantee regular payments over time. Most life insurance companies handle these annuities and long-term payment structures.

Then, you have the plaintiffs and defendants. These people have been wronged and are now on the receiving end of structured settlement payments. On the flip side, companies or insured individuals generally owe the plaintiff due to some liability.

Legal professionals, like lawyers and law firms, play a pivotal role, representing plaintiffs and defendants throughout the lawsuit, leading to a structured settlement. 

Settlement brokers come into the picture to assist in negotiating the structured settlement terms. They may also help with purchasing the annuity.

When plaintiffs want to convert their future structured settlement payments into a lump sum, it is done through factoring companies. These companies can buy these rights at a discounted rate. However, this sale process is regulated and requires court approval to ensure it’s in the plaintiff’s best interest.

Investors come into play by providing capital to factoring companies or directly purchasing the rights to structured settlements. They make their profits based on the difference between the lump sum they pay and the total value of the future payments, much like buying wholesale and selling retail.

Regulatory bodies keep a watchful eye on the structured settlement sale process to prevent abuse. Different states have their regulations, often necessitating court approval for sales. The federal government also steps in, particularly regarding tax treatment. The IRS provides tax advantages for structured settlements, promoting their use and ensuring long-term financial support for plaintiffs.

How To Generate Income

Investing in structured settlements can provide steady returns for investors. 

First, investors can purchase the rights to future structured settlement payments. They may directly buy these rights from the individuals receiving the payments at a discounted rate. Alternatively, they can work with factoring companies that buy these payment rights.

The primary way investors make money is through the difference between the discounted lump sum they pay the annuitant and the total amount of structured settlement payments they receive over time.

Sometimes, factoring companies bundle several structured settlements together and create securities based on the expected future payments. Investors can then buy these securities and earn returns from the collective payment streams.

How To Lose Money

There are potential pitfalls that investors need to be aware of.

Firstly, let’s consider default risk. This can happen when the insurance company responsible for annuity payments runs into financial trouble or even bankruptcy. The expected payments might fail to happen.

Another potential pitfall is insufficient due Diligence. Please thoroughly check the validity of the structured settlement or the insurance company’s financial strength to avoid complications or defaults down the line.

Regulatory and legal risks are another consideration. Ignoring strict regulations around the sale and purchase of structured settlements can result in troublesome legal issues, penalties, or even the cancellation of purchased rights to future payments.

Then, there needs to be more court approvals. Imagine trying to dock at a port without permission. If proper approval isn’t obtained, the rights transfer could be invalidated, leading to financial losses for the investor.

Overpaying for settlements is another potential problem. An investor must negotiate effectively and accurately assess the value to avoid paying more than necessary, reducing returns, or even causing a loss.

Interest rate risks are also essential to consider. If interest rates rise significantly after purchasing a structured settlement, the value or purchasing power of those fixed payments may decrease, making other investments more attractive.

Inflation risk is another potential concern. Inflation can eat away at the purchasing power of fixed payments over time. If inflation rises unexpectedly, the real value of returns can be lower than anticipated.

Liquidity risk is another potential issue. Structured settlements are long-term investments that may only be easily converted into cash with substantial discounts or fees. If an emergency arises and the settlement rights have to be sold prematurely, the investor may receive less than the invested amount.

Unfavorable contractual clauses are another thing to watch out for. It’s like signing a contract without reading the fine print. Some structured settlement agreements may contain clauses that can reduce payment amounts under certain circumstances. If investors aren’t aware of these, they could see decreasing returns.

Dependency on factoring companies is another potential risk. If investors are indirectly involved through a factoring company, they are exposed to the risks associated with that company. If the factoring company needs to manage the settlements better, it can pose additional risks.

Lastly, changing regulations can impact the profitability or viability of investing in structured settlements. The structured settlement industry is subject to rules, and changes in these can affect the landscape of such investments.

Positives & Negatives Of Structured Settlements


Predictable Income Stream: One significant benefit of investing in structured settlements is their reliable income stream. The payment amounts and schedules are usually fixed and known in advance.

Diversification: Returns from structured settlements often correlate little with stock markets, real estate, and other traditional assets. This can help diversify your portfolio and reduce overall risk.

Protection Against Default: Structured settlements are typically backed by insurance companies with high credit ratings. This provides some assurance that the payments will be made as agreed.

Potential for Competitive Returns: Depending on the purchase price and prevailing interest rate environment, structured settlements can offer returns that are on par with or even better than other fixed-income investments.

Stability: Unlike stocks or bonds, which can be volatile, structured settlements are more stable due to their fixed nature.


Illiquidity: One drawback is their need for more liquidity. Once you’ve invested, it can be challenging to quickly convert that investment back into cash without potentially losing money.

Long-Term Commitment: Many structured settlements span years or even decades. Your money will be tied up for an extended period, so you must be comfortable with this long-term commitment.

Counterparty Risk: While insurance companies with high credit ratings typically back structured settlements, there is still a risk that the issuing company could face financial difficulties. If the company goes under, it could impact the settlement payment.

Regulatory and Legal Challenges: The structured settlement industry is regulated, and there may be legal complexities to navigate, especially when transferring rights to payments.

Interest Rate Risk: If interest rates rise significantly after investing in a structured settlement, the returns on that settlement may be less attractive compared to new market opportunities.

Inflation Risk: The fixed payments from a structured settlement may not keep up with inflation, which means that the actual value of the returns could erode over time.

Due Diligence Required: Before purchasing a structured settlement, it is essential to conduct thorough due diligence to ensure the deal’s legitimacy and fully understand all potential risks.

Investment Opportunity Filter™

The Investment Opportunity Filter™ evaluates an investment opportunity based on cashflow, tax benefits, appreciation, and the leverage it provides.

Structured settlements score a 2/4 with The Investment Opportunity Filter™.

Structured settlements can produce significant cashflow and leverage others’ skill sets, capabilities, networks, and capital. The tax benefits are minimal, and when you sell a structured settlement you are invested in, you will receive a lump sum payment for less than the remaining future payments.


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