Winn Management Group LLC
Updated Filing received by DOL
Winn Management Group LLC, a real estate & rental employer in Boston, Massachusetts, reported 3,750 participants in its health and welfare plan for plan year 2025. Its Form 5500 shows $18M in insurance premiums across 18 contracts and $1.0M in broker commissions and fees. The plan is a mix of insured and self-funded coverage. The Department of Labor received the filing on September 22, 2026, within the extension window.
Who was paid on Winn Management Group LLC's plan
Schedule A, Part I lists each broker or agent paid on each insurance contract and the amount. Totals below add every contract Winn Management Group LLC filed for 2025.
| Broker or agent | Commissions | Fees | Total | Contracts |
|---|---|---|---|---|
| Mercer · Chicago, IL | $881,021 | $160,635 | $1,041,656 | 22 |
| Custom Benefit Programs, Inc. · Hammonton, NJ | $5,149 | $16 | $5,165 | 3 |
| HUB International · Wilmington, MA | $750 | $0 | $750 | 3 |
| Employee Family Protection, Inc. · Glastonbury, CT | $47 | $0 | $47 | 1 |
Source: DOL Form 5500 Schedule A, Part I (broker commissions and fees), plan year 2025, as published in EBSA's 2025 "Latest" dataset. Part I names whoever the carrier paid, which can be a firm or an individual agent; both are public record. Amounts exclude pay from carriers not tied to a listed contract.
Insurance contracts and carriers
Every insurance contract reported on Schedule A: carrier, what it covers, people covered at year end, earned premium, and broker compensation.
Source: DOL Form 5500 Schedule A, plan year 2025. Self-funded medical coverage has no premium; amounts shown for it are stop-loss or administrative contracts.
How Winn Management Group LLC compares
Medians across employers for plan year 2024, the most recent complete year. Commission rates use fully insured medical contracts only; dollar medians use every employer that disclosed broker pay.
Not computable: no insured medical premium on the filing.
Premium per covered person on medical contracts: $7,616 a year (national median $7,274).
Source: BenefitsLedger benchmarks from 58,547 employer health plans with 100 or more participants, plan year 2024. Methodology.
Year over year
| 2024 | 2025 | Change | |
|---|---|---|---|
| Participants | 3,597 | 3,750 | +4.3% |
| Premiums filed | $13,277,629 | $17,633,816 | not comparable |
| Broker commissions + fees | $945,851 | $1,047,618 | +10.8% |
| Commission rate | — | — | — |
Source: DOL Form 5500 filings for plan years 2024 and 2025.
Filings and timeliness
Plans this employer filed under its EIN with a health benefit code. Large plans are due seven months after the plan year ends, or two and a half months later with an extension; amended filings carry the amendment date, so no timing is asserted for them.
| Plan | Plan year end | Received by DOL | Timing | Participants |
|---|---|---|---|---|
| Winn Management Group Welfare Plan#501 · insurance, general assets | December 31, 2025 | September 22, 2026 | within extension | 3,750 |
Source: DOL Form 5500 Part I and signature dates; "late" means received after the extended deadline (the 15th day of the tenth month after plan year end). What a late Form 5500 costs.
How much did Winn Management Group LLC pay in health insurance broker commissions in 2025?
Winn Management Group LLC's 2025 Form 5500 reports $1,047,618 in broker commissions and fees across 18 insurance contracts ($886,967 in commissions, $160,651 in fees), with Mercer receiving the largest share.
Is Winn Management Group LLC's health plan self-funded or fully insured?
The 2025 filing indicates the plan is a mix of insured and self-funded coverage. Medical coverage is written by Blue Cross Blue Shield of Massachusetts, Inc., Hawaii Medical Service Association, Kaiser Foundation Health Plan Inc.
How does Winn Management Group LLC's broker compensation compare with similar employers?
A commission-to-premium ratio cannot be computed for Winn Management Group LLC because the filing does not report medical premium on Schedule A (usual for self-funded plans). In dollars, employers with 1,000-4,999 participants that disclosed broker pay reported a median of $168,579.
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Record built October 24, 2026 from U.S. Department of Labor, EBSA Form 5500 datasets (2025, 2024, 2023 plan years, 'Latest' files). Filings can run 7 to 10 months behind the plan year; always confirm against current plan documents. BenefitsLedger is not affiliated with the U.S. Department of Labor. Open the DOL filing search.