Medicare Made Simple (Seriously)

Thomas Connolly is an independent Medicare and health insurance specialist with over 40 years of experience in the financial services industry. He began his career at John Hancock, where he helped individuals and families build financial plans and protect their long-term security. Over the years, he transitioned to independent practice, working directly with consumers, employers, and advisory professionals to improve healthcare decision-making within retirement planning.

For the past 15 years, Mr. Connolly has focused his work exclusively on the Medicare marketplace, now serving clients across 17 states nationwide. His expertise includes Medicare Coordination, Medicare Supplement (Medigap) policy comparisons, Medicare Advantage (HMO/PPO) strategies, Part D drug coverage analysis, and financial assistance integration through Medicaid and Medicare Savings Programs.

A core part of his professional mission is to demystify Medicare for financial advisors and their clients. Mr. Connolly has authored multiple educational guides explaining how:

• Payroll tax history funds Medicare Part A,
• Medicare Part B functions as a pay-as-you-go model,
• Supplemental coverage is required to fill the 20% cost gap,
• Standalone Part D plans coordinate drug benefits,
• Medicare Advantage plans integrate ancillary benefits such as dental, vision, hearing, OTC, and transportation.

His national Medicare “cookbook” series provides step-by-step visual illustrations of Medicare Part A, Part B, supplemental plans, and Part D drug coverage, alongside real-world cost modeling, out-of-pocket exposure analysis, and carrier-based enrollment considerations.

Mr. Connolly is also one of the few Medicare planners who integrates Medicaid and income-based financial assistance into Medicare planning. His training outlines how the Medicare Savings Program (MSP) and other financial assistance mechanisms can reduce or eliminate Part B premiums, drug copays, and other medical costs—critical information for financial advisors seeking to retain clients and control healthcare-related spending in retirement portfolios.

His curriculum further teaches advisors to navigate the complex enrollment pathway for workers delaying Medicare past age 65, including employer coverage verification, SSA portal registration, multi-factor identity verification, credible drug coverage documentation, penalty avoidance strategies, and state-level underwriting restrictions for Medigap transitions.

Mr. Connolly’s philosophy is simple: Medicare is not just insurance — it’s a financial planning event. A well-structured Medicare plan protects retirement income, preserves client relationships, and prevents avoidable penalties and gaps in care.