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Sears Holdings Employees: 10 Critical Estate Planning Steps After the 2025 Tax Law

“Sears Holdings employees should proactively revisit their estate and trust strategies—incorporating adjustable trust provisions, state-level mitigation tactics, and digital asset protocols under the new law—and consult a qualified legal or tax advisor for individualized guidance.” – Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

“Sears Holdings employees would be well advised to integrate flexible trust provisions, state-level tax strategies, and digital asset instructions into their legacy plans—and consult a legal or tax advisor to tailor these measures to their circumstances.” – Patrick Ray, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

The key federal and state tax exemption updates and their planning implications.
How trust taxation, long-term care funding, and digital asset protocols have changed under the new law.
Key strategies for business succession and legacy preservation.

Sears Holdings employees should conduct a thorough review of their legacy arrangements in light of the major federal estate and gift taxation changes introduced by the One Big Beautiful Bill Act of 2025. Though high net worth households have drawn much of the spotlight, these updates impact everyone managing health care funding, retirement savings, and intergenerational asset transfers.

First , the Act permanently raises the federal estate, gift, and generation-skipping transfer tax exemption to $15 million per individual and $30 million for married couples. While this allows more assets to pass free of federal tax, the political landscape remains unsettled; if control of Congress shifts, senators like Elizabeth Warren and Bernie Sanders could push to reduce exemptions. Sears Holdings employees can build in flexibility by using adjustable trust provisions or formula clauses in wills to adapt to future legislative shifts.

Second , even though the prior “sunset” clause on exemptions is gone, Congress still has the power to roll back benefits. A change in legislative majority could restore lower exemption levels. To lock in current advantages without sacrificing flexibility, consider contingency vehicles such as charitable lead trusts and grantor retained annuity trusts (GRATs) tailored to your planning needs.

Third , the new law compresses trust income tax brackets and alters distribution rules, accelerating the point at which the highest rates apply for undistributed income. Sears Holdings employees should review existing irrevocable trusts and evaluate tiered distribution strategies to limit accelerated taxation and help preserve assets for beneficiaries.

Fourth , several states—including Massachusetts, Oregon, and Minnesota—still impose estate or inheritance taxes with exemption thresholds far below federal levels (for example, Massachusetts taxes estates over $2 million at up to 16%). Incorporating state-level exposure into planning, perhaps through state-qualified charitable remainder trusts or spousal lifetime access trusts (SLATs), may help Sears Holdings employees mitigate unexpected liabilities.

Fifth , according to Genworth’s 2024 Cost of Care survey, the median annual cost of a nursing home is $108,405 and a semi-private room averages $96,060. ¹ With long-term care expenses rising and potential Medicaid funding cuts on the horizon, Sears Holdings employees may benefit from Medicaid asset protection trusts or commercial long-term care insurance, taking into account individual health trends and premium deductibility under IRS rules.

Sixth , the law preserves or increases tax deductible limits for qualifying long-term care insurance premiums, ranging in 2025 from $450 for those under 40 to $5,640 for anyone over 70. Confirming that policies meet IRS Section 213(d) criteria helps Sears Holdings employees claim every available deduction.

Seventh , IRAs, Roth conversions, and income shifting techniques are affected by the Act’s revised individual income tax rules. Although the top rate remains 37%, phased-out deductions and new bracket thresholds may raise taxable income. Sears Holdings employees can coordinate retirement distributions with estate planning—such as using IRA assets to fund charitable remainder trusts—to lower overall tax exposure and help preserve legacy value.

Eighth , changes to grantor trust status, minority interest treatment, and valuation discounts directly influence family owned business successions. Sears Holdings employees involved in closely held enterprises should examine buy-sell agreements, equity freeze techniques, and liquidity planning to facilitate effective transfers and address potential estate tax obligations.

Ninth , digital assets must now be explicitly addressed in wills, trusts, and powers of attorney. Clear transfer instructions and designated fiduciaries are vital for online banking accounts, digital wallets, and cryptocurrencies. Establishing a digital asset memorandum with custodial details and wallet access protocols can help Sears Holdings employees preserve these holdings.

Tenth , comprehensive estate planning goes beyond taxes to encompass guardianships, philanthropic goals, and family values. Whether it’s donor advised funds, multigenerational wealth education, or special needs support, updating documents ensures they reflect current priorities. Sears Holdings employees should review plans regularly to align with evolving family circumstances.

All things considered, the 2025 tax law demands a holistic reassessment of estate plans—covering exemption thresholds, trust taxation, state exposures, long-term care funding, tax planning interplay, business succession, digital asset stewardship, and broader legacy objectives. By engaging a seasoned estate planning attorney and working with a trusted financial advisor, Sears Holdings employees can preserve flexibility for an uncertain legislative future while aligning documents with current law.

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Sources:

1. Business Wire. “ Genworth and CareScout Release Cost of Care Survey Results for 2024 .” Business Wire , 4 Mar. 2025.

2. Assaf, Rita. “ While Over 70 % of Retirees Say Retirement Is Going as Planned, Confidence in Retirement Outlook Is Down Among Pre-Retirees .” Fidelity Investments , 11 Mar. 2025.

3. Watson, Garrett, et al. “ “One Big Beautiful Bill Act” Tax Policies: Details and Analysis .” Tax Foundation , 4 July 2025.

4. Internal Revenue Service. “ Eligible Long-Term Care Premium Limits .” Internal Revenue Service , 2024.

5. Dangremond, Samuel. “ How to Protect Digital Assets in an Estate Plan .” Real Property, Trust and Estate eReport , American Bar Association, 26 Feb. 2025.

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.

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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.