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    Home»Personal Finance»Credit & Debt»I Believe John Oliver Was Too Kind to ‘Cash Now’ Predators
    Credit & Debt

    I Believe John Oliver Was Too Kind to ‘Cash Now’ Predators

    Money MechanicsBy Money MechanicsJune 16, 2026No Comments6 Mins Read
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    I Believe John Oliver Was Too Kind to ‘Cash Now’ Predators
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    On a recent episode of his HBO Max show, Last Week Tonight, John Oliver leveled a brutal attack on JG Wentworth and other financial companies that promise “fast cash” for structured settlement injury victims.

    His commentary has racked up 1.8 million YouTube views, so it clearly struck a nerve. Watch for yourself (Caution: Strong, but, in my opinion, appropriate language):

    Structured Settlements & Factoring Companies: Last Week Tonight with John Oliver (HBO) – YouTube
    Structured Settlements & Factoring Companies: Last Week Tonight with John Oliver (HBO) - YouTube


    Watch On

    A fellow attorney and friend who’s spent her career representing accident victims called me this week and asked if I’d seen Oliver’s comments and wanted to know whether I thought he was too harsh.

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    After 30 seconds of talking about it, we realized we both had the same reaction: Oliver wasn’t too tough on these financial predators. He wasn’t tough enough!

    Since 1982, federal law has recognized structured settlements as a voluntary option for accident victims who take a settlement in an annuity with payments exempt from federal and state income tax.

    The system worked well until the late 1990s, which is when “fast cash” predators started fleecing accident victims of their financial security.

    In response to this, Congress and most states, passed laws that mandated better disclosure, present-value calculation of future payment rights and judicial oversight with a “best interest” standard for the victim. Backers called these laws structured settlement protection acts, or SSPAs.

    The takeaways

    My attorney friend and I agreed that Oliver’s commentary had two important takeaways:

    One, attorneys and anyone who works with accident victims must warn clients about the dangers of these predatory “cash now” companies. And if the client has a brain injury, the court should be encouraged to appoint a guardian ad litem — basically, a part-time overseer who’ll protect the client’s interests.

    As a longtime supporter of structured settlements, I can tell you that, without the presence of that “guardian,” the sale of structured settlement payments or cashing in the entire annuity is seldom a good idea. Because of the losses that would be incurred — as the structured settlement is “sold” at a discount — rarely is it in the accident victim’s best interest.

    And two, any public official who thinks the federal 2002 “model protection act” solved this structured settlement problem is delusional. It required only court approval before the sale of the annuity, but did not require courts to evaluate the fairness of the transaction itself, only that the sale complied with individual state SSPAs.

    For decades, I have represented accident survivors, often encouraging them to take annuities instead of a single lump sum. I can’t recall a single instance when a client who wanted to sell future payment rights would have been better off to do so, with one exception: One of my clients became a paraplegic, and he spent the money helping his family out of poverty.

    In the few others who ignored my advice, thousands of dollars went to buying cars for girlfriends, making loans to friends and family that were never repaid and, in one case, buying a bowling alley that was in bankruptcy. So much money, just squandered.

    After watching Oliver’s show and speaking with my fellow trial attorney, I wanted a perspective from inside the structured settlement industry. So I called Peter Arnold, a certified structured settlement consultant in Maryland who has organized successful grassroots lobbying efforts for the structured settlement industry.

    “The most telling aspect of today’s structured settlement protection laws,” he said, “is that they were supported by the same predatory companies who were abusing injury victims. That should’ve been a huge red flag that the law was toothless, but Congress and even many in the insurance industry ignored it. Congress just wanted a fig leaf to let them pretend they did something.”

    My recommendations

    So what should you do if you or someone you know is considering selling structured settlement payment rights to one of these predators? Here are a few suggestions:

    Check with an attorney. If an attorney negotiated the settlement, see whether they will evaluate the proposed contract, including how much the company will pay for the rights it receives to the annuity payments. If it’s a sham deal, the attorney should be able to spot it quickly.

    Don’t let the “cash now” company railroad the agreement through a judge. Federal law encourages court approval of these transactions, but some judges see themselves as rubber stamps.

    At a minimum, make sure the judge has full knowledge of all medical issues, including anything that might affect the injury victim’s judgment. Be clear about this even if the company buying payments says to downplay it.

    Get multiple bids and make sure these bids come from separate buyers. JG Wentworth does business under multiple names, and according to Arnold, they may not tell you this even when they know you already have a bid from a sister company.

    “It’s an underhanded way to make you think you’re getting a second bid when you’re not,” Arnold said.

    If you’re still negotiating your injury settlement, get your structured settlement broker’s corporate policy on sharing your data. Most brokers who work with accident victims to design future payments are fine people. But every group has a few sleazebags.

    For years, there have been indications that some brokers discreetly sell client information to companies like JG Wentworth. This could include the size of your settlement and your payment schedule.

    If you find out this has happened, you may have a legal claim for violation of your right to confidentiality.

    I’ll say again that, in my entire career as a legal advocate for accident victims, I have almost never seen someone with a structured settlement who would be better off by doing a “cash now” deal.

    I wrote this story years ago that is right on point, and each time I read it, I feel so angry, so disappointed.

    If you or someone you know feels like there is no other way than to sell their payment rights on a structured settlement, then, at the least, don’t fall for someone pushing you into a quick sale — and make sure to get independent advice.

    Dennis Beaver practices law in Bakersfield, Calif., and welcomes comments and questions from readers, which may be faxed to (661) 323-7993, or e-mailed to Lagombeaver1@gmail.com. And be sure to visit dennisbeaver.com.

    Related Content

    This article was written by and presents the views of our contributing adviser, not the Kiplinger editorial staff. You can check adviser records with the SEC or with FINRA.



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