Sears Holdings Employees Face Mounting Health Insurance Costs—How Rising Expenses Could Impact Financial Stability
Healthcare Provider Update: Healthcare Provider for Sears Holdings
Sears Holdings typically provides healthcare benefits to its employees through various insurance plans, often with national insurers such as Aetna, UnitedHealthcare, or Anthem Blue Cross Blue Shield being among the health carriers they have partnered with. The specific providers can vary by location and employee selection during open enrollment periods.
Potential Healthcare Cost Increases in 2026
As we progress into 2026, the healthcare landscape is expected to face significant challenges, particularly for employees of Sears Holdings. Forecasts indicate steep premium hikes, with some states imposing increases of over 60%, largely influenced by rising medical costs and the potential expiration of enhanced ACA premium subsidies. The Kaiser Family Foundation highlights that without congressional intervention, millions of marketplace enrollees could see their out-of-pocket costs surge by more than 75%. This convergence of factors threatens to impose a substantial financial burden on both individuals and employers, necessitating proactive strategies to mitigate rising expenses.
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'Rising health care costs have become a silent strain on long-term financial wellness, and Sears Holdings employees should regularly evaluate their benefit options and adjust their retirement plans to keep pace with medical inflation,' – Michael Corgiat, a representative of The Retirement Group, a division of Wealth Enhancement.
'With health care expenses climbing faster than wages or inflation, Sears Holdings employees must treat medical costs as a core part of their retirement strategy, not an afterthought, to maintain lasting financial resilience,' – Brent Wolf, CFP®, a representative of The Retirement Group, a division of Wealth Enhancement.
In this article, we will discuss:
How rising health insurance costs are reshaping employee and retiree financial outlooks.
The impact of health care inflation on long-term retirement readiness and workforce dynamics.
Practical strategies to manage escalating medical expenses and maintain financial resilience.
Rising Health Insurance Costs Are Driving Growing Financial Difficulties
by Brent Wolf, CFP®, Wealth Enhancement
The rising cost of health insurance continues to strain budgets across the nation. For Sears Holdings workers and retirees, higher premiums expected for 2026 could significantly affect long-term fiscal outcomes. Pharmaceutical inflation, institutional inefficiencies, and soaring medical expenses have combined to make health care one of the most persistent budget pressures of this decade.
“One of the most destabilizing factors in personal finance is health care,” said Brent Wolf, CFP®, of Wealth Enhancement. Because premiums, copays, and deductibles tend to increase faster than both income and inflation,
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even Sears Holdings professionals with competitive compensation packages may feel the tightening impact.
A Stressed-Out Health Care System
According to the Kaiser Family Foundation (KFF) 2025 survey, employees now contribute $6,850 on average toward the annual cost of employer-sponsored family health coverage (with total premiums surpassing $26,993 nationwide)—an increase of roughly 7% from last year and up 26% since 2020.
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Hospital consolidations, postponed care during the pandemic, and high prescription drug costs have created the perfect storm. As deferred treatments resume, utilization surges—leading insurers and large employers, such as Sears Holdings, to shift a greater portion of costs to workers.
According to Wolf, “the system is under immense pressure.” Retirees are seeing similar inflation in their Medicare supplement premiums, while employers are balancing how much of those costs to absorb versus pass on.
Medical breakthroughs, from targeted cancer therapies to weight-loss medications, are improving outcomes but driving costs higher. Meanwhile, for-profit intermediaries and opaque pricing structures continue to inflate overall health care spending.
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The Unspoken Effect on Future Financial Readiness
Rising health care costs quietly eat into retirement readiness. Many Sears Holdings employees nearing retirement underestimate how much medical expenses may increase once paychecks stop.
“Most people include taxes and living expenses in their retirement plans, but they don’t consistently account for medical inflation,” Wolf explained. “Health care can easily consume 20% to 30% of a retiree’s budget—and that figure continues to grow each year.”
For current workers, rising premiums can limit 401(k) contributions or reduce savings rates. A Sears Holdings employee who reduces retirement plan contributions by $500 per month to offset health care costs could lose over $1 million in potential retirement assets over 30 years. “That’s the hidden cost few people calculate,” said Wolf.
Employers Reevaluating Their Position
Many corporations are reassessing how to balance premium subsidies and employee well-being. For companies like Sears Holdings, maintaining comprehensive health coverage is a key part of retaining experienced talent and safeguarding long-term productivity.
“Organizations that absorb a greater share of premiums typically see higher engagement, lower turnover, and stronger morale,” Wolf said. “While the upfront cost is high, the return is often a healthier, more stable workforce.”
However, smaller industry players and contractors may not have the same flexibility. Wolf advises workers to assess total compensation—including health care contributions—when evaluating job opportunities.
“It’s effectively a 5–10% raise if your employer covers half your premium,” Wolf added. “Recognizing those hidden compensation advantages is vital for long-term planning.”
How to Handle Medical Expenses
Wolf recommends several steps for Sears Holdings employees to manage health care costs and help strengthen long-term fiscal positioning:
1. Take full advantage of employer benefits. Use available premium-sharing programs, flexible savings accounts (FSAs), and health savings accounts (HSAs). HSAs, in particular, offer triple-tax advantages that can significantly reduce future health care burdens.
2. Incorporate medical cost inflation in retirement plans. Health care costs should be assumed to rise at least 5% annually, especially for those with chronic health concerns or long-term care needs.
3. Compare Medicare and supplemental plans carefully. Lower premiums can mask higher long-term expenses due to limited coverage or prescription restrictions.
4. Review coverage each year. The annual open enrollment period provides a chance to identify network changes or premium adjustments before they negatively affect your budget.
5. Plan early for long-term care. With private nursing home costs averaging more than $100,000 annually,
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hybrid life insurance or long-term care coverage can help preserve accumulated assets.
The Wider Financial Consequences
Rising health care costs influence more than personal budgets—they shape national economic patterns, retirement timing, and workforce participation.
“Health care expenses pose a real threat to long-term wealth for many,” Wolf warned. “They affects when people can afford to retire, how long they remain in the workforce, and how sustainable their income will be afterward.”
According to KFF research, health care premiums grew 6% since 2024, compared to a 4% rise in worker earnings and a 2.7% rate of inflation.
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For Sears Holdings employees, this imbalance underscores the need for proactive planning.
Creating a Long-Term Financial Structure
Wolf stresses that health care should be integrated into your overall financial strategy, not treated as a fixed expense. For Sears Holdings employees, that means crafting retirement and investment plans that can weather ongoing medical cost pressures.
“Finding the cheapest plan isn’t the goal,” Wolf said. “The goal is to build a financial structure that supports your family, your health, and your long-term fiscal well-being. Health care is not just a cost—it’s a cornerstone of long-term budget health.”
A study by Milliman Inc. found that a healthy 65-year-old retiring in 2025 may face lifetime health care costs of approximately $275,000 (men) to $313,000 (women) under Original Medicare with Medigap and Part D coverage.
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Retiring five years earlier could increase those lifetime costs by roughly 56%.
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Health care inflation—combined with premiums surpassing $25,000 per year and a 26% rise in health insurance costs since 2020—has created a new fiscal reality for Sears Holdings employees and retirees alike. By leveraging HSAs and FSAs, accounting for annual medical cost inflation, and reassessing coverage each year, individuals can take active steps toward conserving long-term budget health.
Think of health care expenses as a slow leak in your financial tank. Each copay or premium increase might seem minor, but over time, it drains the resources meant for a dependable retirement. Like a skilled engineer maintaining vital equipment, Sears Holdings employees must monitor their health care costs, plug fiscal leaks early, and fortify their plan before small issues become costly impairments.
About the Author
Financial planner Brent Wolf, CFP®, of Wealth Enhancement , focuses on health care expense planning and retirement income strategies. He helps clients align their medical coverage with broader fiscal goals to maintain long-term stability amid changing market and health care conditions.
How does the Sears Holdings Pension Plan differentiate between normal retirement, early retirement, and late retirement options for Kmart participants? In what ways do these options influence the retirement planning process for employees of Sears Holdings, and what specific considerations should Kmart employees be aware of when choosing one of these retirement paths, particularly in relation to their vested status?
Differentiation of Retirement Options: The Sears Holdings Pension Plan offers distinct options for normal, early, and late retirement. Normal retirement is available at age 65 or after five years of plan participation, whichever is later. Early retirement can be taken from age 55 but before 65, provided the employee is vested, with benefits subject to actuarial reduction unless certain conditions are met (like having at least 90 points, which is a sum of age and years of credited service). Late retirement pertains to any retirement after the normal retirement age, with pensions recalculated to reflect the delay in benefit commencement.
Considering the frozen status of the Sears Holdings Pension Plan, how does this impact the benefits eligibility for Kmart employees, and what implications does it have for their retirement savings strategies? In what ways should current employees factor in this frozen status when evaluating their overall retirement readiness and potential alternatives outside of the company plan?
Impact of Frozen Status: The freezing of the Sears Holdings Pension Plan on January 31, 1996, means that there have been no new accruals of benefits or participants since that date. For Kmart employees, this impacts their benefits eligibility by capping the pension benefits at levels earned up to the freeze date. Employees need to consider this stagnation in benefits when planning for retirement, potentially seeking additional retirement savings avenues to bridge any shortfall.
What are the essential calculations involved in determining the retirement benefits under the Sears Holdings Pension Plan for Kmart employees? Specifically, how do the Career Average Pay and Final Average Pay formulas come into play, and what factors should employees consider when estimating their future retirement payouts?
Essential Calculations for Retirement Benefits: Pension benefits for Kmart employees under the Sears Holdings Pension Plan are calculated using either the Career Average Pay or the Final Average Pay formulas. These calculations take into account an employee's years of credited service and compensation up to the freeze date. Factors like estimated Social Security benefits and specific formulas (such as a deduction based on Social Security benefits under the Final Average Pay formula) play crucial roles in determining the final pension payout.
How can Sears Holdings employees best navigate the process of applying for benefits under the Pension Plan? What specific steps should participants take to ensure their applications are processed correctly, and what important deadlines should they be aware of to avoid any negative consequences on their retirement benefits?
Navigating the Benefits Application Process: To apply for pension benefits, employees must submit a formal application, ideally 30 to 90 days before the intended commencement date. It is crucial to ensure all personal information, including marital status and spouse details, is up-to-date to avoid delays or inaccuracies in benefit processing. Missing application deadlines can lead to postponed benefit payments or unwanted default options.
In what situations can Kmart employees expect to receive a Deferred Vested Pension, and how is the calculation for this pension affected by their previous employment and vesting service? Employees should be aware of the important factors influencing their eligibility and the steps necessary to maintain their retirement benefits after leaving the company.
Eligibility and Calculation for Deferred Vested Pension: A Deferred Vested Pension is available to employees who leave the company after becoming vested but prior to qualifying for retirement. The calculation mirrors that of a normal retirement pension, with possible early commencement reductions. Understanding the timing of benefit commencement and the potential reductions for early start is vital for planning.
How does the Sears Holdings Pension Plan address tax considerations for employees receiving both monthly payments and lump sum payments upon retirement? What tax implications should Kmart participants be aware of, particularly in relation to IRS rules for distributions and potential penalties for early withdrawal?
Tax Implications of Pension Receipt: Pension payments, whether monthly or lump sum, are subject to federal taxes. Monthly benefits are taxed as ordinary income, while lump sums might be eligible for special tax treatments or rollover options to defer taxes. It’s important for Kmart employees to consider these implications and possibly consult with a tax advisor to optimize tax liability.
What are the rights and protections afforded to Kmart participants under the Employee Retirement Income Security Act (ERISA) as they navigate their retirement benefits with the Sears Holdings Pension Plan? How can employees leverage these rights to ensure they are receiving all the benefits to which they are entitled?
ERISA Rights and Protections: Under ERISA, Kmart employees are entitled to certain rights including the ability to appeal denied benefits, access to plan information, and assurances of fair and equitable treatment of their benefits. Leveraging these protections ensures that employees receive all due benefits.
What steps should Kmart employees take to update their personal information to ensure they continue receiving their benefits without interruption, especially in the context of missing participants or uncashed checks? What resources and contacts at Sears Holdings are available to assist with these updates?
Updating Personal Information: Maintaining accurate personal information with the pension plan is crucial for uninterrupted benefit payments. Employees should promptly update changes such as address, marital status, or beneficiaries to prevent issues with benefit distributions or lost checks.
How does the process of transferring between affiliated employers impact pension benefits for Kmart employees under the Sears Holdings Pension Plan? What considerations should be taken into account concerning Credited Service and Vesting Service during such transfers, and how can employees ensure they do not lose any entitled benefits?
Impact of Transfers Between Affiliated Employers: Transferring between Sears Holdings’ affiliated employers can affect pension benefits differently depending on whether the employer participates in the pension plan. It's essential to understand how such transfers impact credited and vesting service accruals.
For Kmart employees seeking more information about their benefits under the Sears Holdings Pension Plan, what is the best way to contact company representatives? How can they effectively communicate their questions or concerns to ensure they receive accurate and timely information regarding their retirement benefits?
Contacting Plan Representatives: Kmart employees seeking clarity on their pension benefits should contact the Sears Holdings Pension Service Center. Effective communication, including prepared questions and necessary documentation, will aid in obtaining accurate and comprehensive information.
With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.
Sears Holdings Corporation's pension plans were taken over by the Pension Benefit Guaranty Corporation (PBGC) following the company's bankruptcy. The two defined benefit pension plans have been frozen since 2005, meaning no new benefit accruals are added. The plans are underfunded by approximately $1.4 billion, with PBGC assuming responsibility to ensure pension payments continue. These plans cover about 90,000 participants who worked for Sears, Roebuck and Co., and Kmart Corporation. Despite the underfunding, PBGC is expected to cover the vast majority of pension benefits owed under these plans. Participants can manage their benefits and verify information through PBGC's online platform or service center.
Bankruptcy and Store Closures: Sears Holdings emerged from bankruptcy with significant store closures, reducing from nearly 700 stores to less than 25. The company has been liquidating its remaining assets and recently announced more store closures in 2024. The focus is on resolving bankruptcy-related issues and managing the liquidation process effectively (Sources: The Layoff, Yahoo Finance).
Sears Holdings offered both RSUs and stock options before its bankruptcy. RSUs vested over time, providing shares, while stock options allowed employees to buy shares at a fixed price.
Sears Holdings, now part of Transformco, has faced numerous challenges in recent years, impacting its ability to provide comprehensive employee healthcare benefits. The strategic transformations initiated since 2017 aimed to improve operational performance and liquidity, which included measures such as obtaining additional loan proceeds and real estate sales. However, the company's financial struggles and store closures have also led to significant changes in employee benefits, including healthcare. As part of its efforts to stabilize and restructure, Sears has focused on reducing outstanding debt and pension obligations, contributing almost $4 billion to its pension plan since 2005 due to prolonged low interest rates. In 2023, Transformco continued to navigate its financial challenges, which have influenced its healthcare benefits offerings. The company has aimed to maintain basic healthcare coverage for its employees despite ongoing restructuring efforts. This includes providing access to medical, dental, and vision plans, although the specifics of these benefits and any enhancements over the past years have been less prominently highlighted compared to the broader financial strategies and operational changes. The focus on financial stability and cost reduction remains critical for Transformco as it seeks to ensure the viability of its employee benefits programs amid economic uncertainties.
For more information you can reach the plan administrator for Sears Holdings at 3333 beverly road Hoffman Estates, IL 60179; or by calling them at 1-800-697-3277.
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