For those who follow the NFL, now out-of-retirement NFL quarterback Philip Rivers made a comeback to the sports world by returning to the Indianapolis Colts in late 2025 after a five‑year retirement.

Personally, his comeback gave me hope that my dream of becoming a professional sports player isn’t over! For those who aren’t Uncle Rico from Napoleon Dynamite, probably the more important takeaway was what River’s return meant for his family healthcare benefits, and how it applies especially to those contemplating retiring from the airlines early.

Background

Rivers entered the NFL as the number four pick in the 2004 NFL Draft, originally selected by the Giants and immediately traded to the San Diego Chargers in the Eli Manning swap. He played 16 seasons with the Chargers (2004-2019), becoming one of the franchise’s defining players. In 2020, he spent one season with the Indianapolis Colts, leading them to an 11–5 record and a playoff berth before initially retiring.

His career culminated at his retirement with eight Pro-Bowl appearances, 397 career passing touchdowns and 59,271 passing yards, ranking among the NFL’s all‑time leaders. He also had 242 consecutive starts—the second‑longest streak ever for a quarterback.

River’s journey back to the NFL began last December when the Colts found themselves in a tough situation—their starter, Daniel Jones, suffered a torn achilles. Backup Riley Leonard also went down with an injury. This left the team desperate for a seasoned quarterback capable of stepping in immediately.

The Colts called Rivers and in his first game back, he completed 18 of 27 passes for 120 yards, one TD, and one interception in an 18-16 loss to Seattle. He showed surprising command and calm after 1,800 days away from the NFL.

Beyond Football

Rivers is almost as well known for his large family as for his football career: He and his wife, Tiffany, have ten children, and in 2024 he became a grandfather when his eldest daughter welcomed a baby boy. Before returning to the NFL, Rivers spent his retirement years coaching his sons’ high-school team in Alabama.

His players and family watched his 2025 comeback game together in a restaurant. His children expressed everything from excitement to nervousness. As Rivers recounted, his younger kids, “…don’t remember Dad playing,” while his older daughters were shocked to see him take the field again after growing up during his Chargers years.

The family dynamic wasn’t just emotional—it was also practical. A family of 12 depends heavily on access to health coverage. NFL players receive five years of league‑funded health and dental insurance after retirement. Rivers’ original coverage was set to expire in August 2026. By returning to active status, he effectively reset that five‑year clock, securing coverage for himself, Tiffany, and their 10 children well into 2031!

Before we start feeling too happy for Rivers’, he did accumulate over $244 million in career earnings. That said, for airline employees, the story resonates. It underscores how benefits, particularly health coverage, can drive major career decisions especially when evaluating early retirement. Understanding your options for healthcare is essential. Rivers’ move is an extreme example, but the principle is universal: for those approaching or in retirement, don’t overlook the costs of healthcare and insurance.

Airline Pilot Families

For many airline pilots and their families, the idea of retiring before the FAA mandated retirement age of 65 (and importantly, Medicare) is a major part of their financial plan and goals.

I’m going to go out on a limb and say that most of us aren’t going to get the call from an NFL franchise so that probably shouldn’t be “Plan A” for securing health and employee benefits in retirement. However, I’m a Cleveland Browns fan…so I might have a chance!

For the rest of us, if you’re contemplating early retirement from the airlines don’t underestimate healthcare costs before Medicare age of 65. For active employees, healthcare costs and premiums are highly subsidized by employers. Once you leave the airline, that may change and it’s important to look at all your options for where you can get insurance:

1. Private marketplace. This essentially entails “shopping” on your state’s ACA marketplace or HealthCare.gov to find a plan the works for you and your family. While enhanced Federal subsidies are changing and are a hot topic on Capitol Hill right now, reduced income in retirement may mean you do qualify for some form of subsidy.
2. COBRA. In most circumstances, early retirees before age 65 can keep their existing healthcare plan for 18 months. The premiums typically, however, increase 102% of the plan’s cost. While steep, reasons to use COBRA may be if you have already met the deductible/max out-of-pocket expenses for the year or want to keep your existing providers.
3. Will your spouse continue working? If so, you may be able to join their plan and receive employer-sponsored coverage as a spousal dependent.
4. For military, TRICARE provides a tremendous benefit for pilots who are considering early retirement. If you’re an active-duty retiree, you’re eligible for TRICARE immediately. For reservists and National Guard who retire, your eligibility kicks in at age 60. TRICARE does offer TRICARE Retired Reserve. While not as cost effective as for active duty and age 60+ reservist healthcare benefits, it’s worth comparing the costs to your other options if you’re contemplating retirement before age 60.
5. Airline provided pre-Medicare option: Most airlines provide some level of coverage for retirees, but with important considerations.

• • Eligibility: This is typically a combination of your age and years of service with the airline.
  • Benefit: You may be able to keep the same plan that you had while flying, however some airlines force you to choose a different plan. It’s important to review the costs associated with the new plan beyond just the premiums (e.g. deductible, copays, max out of pocket, etc.) as well as network to determine if your current providers will be within the new plan.
  • Costs. Some airlines make this 100% pilot paid, a percentage (almost always higher than when you were on active service) or a cost-share based on years of service.

Plan for younger spouses and dependents. Even if you retire at age 65, if you have a spouse or dependent who is younger, it’s important to plan for their healthcare costs once you leave the airline. Some airlines offer dependent coverage for retirees or allow the use of sick time to pay for health insurance premiums.

Save now. One of the best ways to plan for healthcare costs in retirement is to fund an HSA (if participating in a high-deductible eligible healthcare plan) or Health Reimbursement Account (like an HSA but employer funded). For example, United’s Active HRA/RHA is funded by NEC but no longer eligible for 401k contributions. If you have an HSA, consider saving your contributions instead of using them for healthcare expenses today to allow the account value to accumulate. Some plans even allow for an investment account. If you do invest, make sure the asset allocation is aligned to your risk tolerance and time horizon.

The takeaway—healthcare insurance is complicated! if you’re planning on retiring early from the airlines. Recognize that your most expensive cost is likely going to be health insurance before you’re Medicare eligible at age 65. There are lots of factors to consider when planning. Make sure you consider costs (beyond just premiums), providers/network coverage and all options in your financial planning. Plan B: The NFL combine starts February 23in Indianapolis. See you there!

Fly safe!

~Andy