The Latest News & Industry Insights

Thoughts & Insights

Stay up to date with The Westport Group and our continued innovation of insurance solutions for industry leaders.

News

May 7, 2026

America’s Warrior Partnership and The Westport Group Sail Defender with Sail No. 1776 at the 2026 Figawi Race to Honor America’s 250th Birthday

(Braintree, Mass. – May 7, 2026) The Westport Group (TWG), a veteran-operated business based in Braintree, MA, is teaming up with America’s Warrior Partnership (AWP) for the seventh year in a row as they return to the starting line of the iconic 2026 Figawi Race, held Memorial Day weekend, May 22–25, 2026, sailing from Hyannis to Nantucket.

TWG Admin

News

June 2, 2025

TWG and AWP Sail to Victory

(Braintree, Mass. – May 30, 2025) The Westport Group (TWG) and America’s Warrior Partnership (AWP) had a fantastic outing at the 54th Annual Figawi Race Weekend in Nantucket, MA. It was a perfect blend of teamwork and spirited competition that resulted in a win for the crew and, more importantly, recognition and support for AWP.

TWG Admin

News

May 30, 2025

Veterans Set Sail Once Again to Fight Suicide After Military Service

(Braintree, Mass. – May 9, 2025) The Westport Group (TWG), a veteran-operated business in Braintree, MA, has once again teamed up with America’s Warrior Partnership (AWP) to race in the time-honored Figawi Race on Memorial Day weekend from Hyannis, MA to Nantucket, MA. The veteran-led team will be sailing to raise awareness and funds to fight veteran suicide.

TWG Admin

News

April 9, 2025

Veterans Set Sail to Fight Suicide After Military Service

(Braintree, Mass. – May 9, 2024) The Westport Group, a veteran-operated business in Braintree, MA, has teamed up with America’s Warrior Partnership (AWP) to race again this year in the famous Figawi Race on Memorial Day weekend from Hyannis, MA to Nantucket, MA. The veteran-led team will be sailing to raise awareness and funds to fight veteran suicide.

TWG Admin

Thoughts & Insights

April 6, 2025

High-Limit LTD Case Study: A Claimant’s Perspective

Brian was a successful managing partner at a major law firm, when at the age of 49, his cognition became impaired due to complications from an underlying medical condition. During a half-year medical leave, tests showed the cognitive deficit was significant and permanent. The diagnosis was devastating and career- ending for Brian. He would never be able to practice law again and consequently resigned from the firm. He recalled having basic disability coverage and some excess protection that was made available to partners.

TWG Admin

Thoughts & Insights

April 9, 2025

Frequently Asked Questions for Advisors

TWG's High-limit LTD delivers unparalleled protection with higher benefits and seamless integration, ensuring coverage for clients worldwide. We support advisors at every stage, from prospecting to implementation. Curious to learn more? We've answered some commonly asked questions below, but visit our website for a full list of FAQs.

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Thoughts & Insights

April 9, 2025

High-Limit LTD Case Study: Publicly Traded Corporation

The Westport Group’s (TWG’s) High-limit Long-term Disability (High-limit LTD) program protects the specialized compensation protection needs of high-income earners at public and private corporations. Our solutions fill a critical, yet often overlooked, gap in a company’s benefits portfolio enabling brokers to solve this need and enhance their services to their corporate clients.

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Videos

April 9, 2025

TWG’s Influence and Differentiation

The Westport Group is extremely proud to be a Lloyd’s Coverholder. The Lloyd’s marketplace allows us to get enough capacity to offer industry leaders protection in the case of a disability that would replace higher levels of income than traditional group DI products.

TWG Admin

Videos

April 9, 2025

Open Markets, Lineslips and Binders

Lloyd’s policies may differ substantially, however, one thing that they all have in common is that they are backed with Lloyd’s financial security, so you can feel confident in your coverage. Despite being separate, due to the financial structure of Lloyd’s, all syndicates fall under a single market rating dating back to 1992.

TWG Admin

Videos

April 9, 2025

Lloyd’s is a Marketplace

Lloyd’s isn’t an insurance company. It is a marketplace where brokers meet with underwriters to negotiate the transfer of risk. Oftentimes, multiple Underwriters will be on one policy, allowing them to cumulatively take on more risk than they would have the appetite for individually.

TWG Admin

Videos

April 9, 2025

How Lloyd’s of London Started

You may have heard of Lloyd’s of London. For people outside the insurance industry, Lloyd’s often makes headlines when a celebrity takes out an unusual insurance policy. While many are introduced this way, there’s often confusion about what Lloyd’s is and what it does.

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Thoughts & Insights

April 10, 2025

What Should I Look For in a High-limit Long-term Disability Policy: Seamless Integration

Part 1 - Seamless Integration is important at every policy stage

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Thoughts & Insights

April 10, 2025

What Should I Look For in a High-limit Long-term Disability Policy: Flexibility & Customization

Part 2 - Your group is unique – you need flexibility to customize

TWG Admin

Thoughts & Insights

April 10, 2025

What Should I Look For in a High-limit Long-term Disability Policy: Administration & Implementation

Part 3 - Exploring administration and implementation

TWG Admin

Thoughts & Insights

April 10, 2025

TWG’s Introduction to Lloyd’s of London

You may have heard of Lloyd’s of London. For people outside the insurance industry, Lloyd’s often makes headlines when a celebrity takes out an unusual insurance policy.

TWG Admin