A secondary market annuity misnomer surfaced again downtown, in the narrow stretch between the City Café and the Metro Station. The minions were already in position—framing the page from top to bottom—as another SMA label appeared where it never belonged. It’s the kind of sighting that makes the title of this post necessary: Hersch Stern stays in bounds, but the terminology still doesn’t. That distinction—between what someone does correctly and what the terminology still gets wrong—is where the Stern–Lesk contrast begins.
Why the Stern–Lesk contrast matters in the secondary market annuity misnomer
Hersch Stern deserves professional respect. The terminology still doesn’t.
Hersch Stern remains a legitimate, established general agent in Englishtown New Jersey who actually sells annuities in the primary market. That distinction matters. It is a level of professional infrastructure, carrier relationship, and day‑to‑day annuity business that Todd Lesk never had and never operated. Stern has a real platform. Lesk had a website.
But legitimacy in the primary market does not convert factored structured settlement receivables into annuities. And in 2026, Stern is still using the same inaccurate terminology I documented in 2023 and revisited in 2025.
The quality of the receivables he moves is materially higher than the paper historically associated with Todd Lesk. That is also true. But quality does not change structure, and structure is what determines whether something is an annuity.
What Stern Is Doing Right — and What the Terminology Still Gets Wrong
🔹 Stern is a real GA with real annuity business He has carrier appointments, a functioning distribution apparatus, a primary‑market annuity practice, and real compliance infrastructure. Lesk never operated at that level.
🔹 But Stern’s SMA terminology remains inaccurate. When Stern markets “Secondary Market Annuities,” he is not selling annuities. He is selling payment rights sourced from structured settlement factoring transactions, approved under state structured settlement protection acts. The annuity contract remains owned by the qualified assignee. The investor never becomes a policyholder.
🔹 Better‑quality receivables are still receivables Stern’s inventory is generally cleaner and more conventional than the paper Lesk trafficked in. But a high‑grade receivable is still a receivable. The annuity contract never transfers. The investor never becomes a policyholder. State guaranty protections do not apply.
The Line Stern Has Never Crossed
🔹 Stern calls receivables “annuities,” but he does not take the next, far more misleading step of using insurer logos to promote them. That line matters. Once you start using insurer logos to market receivables, you have a foot in regulatory hell. Lesk did — and still does, repeatedly. Stern never has.
Using the wrong word is a terminology problem. Using insurer logos is an implied‑endorsement problem. Stern avoids the latter entirely.
2026 Context: ImmediateAnnuities Still Has the Same Inaccuracy
As of March 7, 2026, ImmediateAnnuities.com continues to publish the following:
“Secondary Market Annuities (SMAs) are policies being transferred by an annuitant pursuant to state transfer laws…”
Every material term in that sentence is wrong:
🔹 Not policies — payment rights transfer, not annuity contracts 🔹 Not by an annuitant — the transferor is a payee in a factoring transaction 🔹 Not annuities — these are factored structured settlement receivables
The persistence of this language — across Stern, Lesk, and ImmediateAnnuities — shows that the misnomer is not a fringe problem. It is structural.
Why This Matters in 2026
The market continues to present receivables as annuities, and consumers continue to assume insurer‑level protections that do not exist.
Stern deserves respect for operating a legitimate primary‑market business and for moving higher‑quality receivables. But the terminology remains inaccurate, and accuracy matters — especially when the structure of the transaction determines who the investor’s obligor actually is, what legal rights the investor does (and does not) have, what protections apply, and what risks are being assumed.
Receivables are not annuities. Not in 2023. Not in 2024. Not in 2025. And not in 2026.
Comparison Table: Stern vs. Lesk (2026)
| Category | Stern | Lesk |
|---|---|---|
| Primary‑market annuity business | 🔹 Yes — legitimate GA with carrier appointments | 🔹 Once had broad FL carrier appointments, but not a GA and activity is now appears minimal |
| Quality of receivables | 🔹 Higher‑grade, more conventional | 🔹 Lower‑grade, inconsistent |
| Terminology (“annuity”) | 🔹 Uses the misnomer | 🔹 Uses the misnomer |
| Use of trademarked insurer logos in marketing receivables | 🔹 No — never | 🔹 Yes — did and still does repeatedly |
| Implied insurer endorsement | 🔹 Avoids it | 🔹 Frequently implies it |
| Accuracy of carrier naming | 🔹 Uses the actual carrier name tied to the underlying annuity contract | 🔹 Improvises carrier names, abbreviations, or hybrid labels as he goes |
| Ratings accuracy | 🔹 Uses the actual carrier rating as published | 🔹 Has made false or misleading claims about insurer ratings |
| Regulatory exposure | 🔹 Moderate — terminology only | 🔹 High — terminology + insurer‑logo use + improvised carrier naming + “Guaranteed to OutPerform” performance claim + false ratings claims |
Related Reading
🔹 2023: Initial analysis of Stern’s SMA terminology (updated March 7, 2025) 🔹 2024: A Stern Warning That Structured Settlement Receivables Are Not Covered by State Guaranty Funds 🔹 2026: ImmediateAnnuities.com still mislabeling receivables as “policies” being transferred by an “annuitant”
Fact Check | Can Structured Settlement Annuities Be Sold? (Updated through March 7, 2026)
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