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Windstream Holdings Employees: Handling Single-Stock Concentration with a Section 351 Strategy

'Windstream Holdings employees with concentrated stock positions should understand that strategies like a Section 351 exchange can offer flexibility in managing large unrealized gains while preserving long-term planning options.' – Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.

'Windstream Holdings employees facing concentrated stock exposure may find that a Section 351 exchange provides an effective way to mitigate risk and maintain control over the timing of potential tax liabilities.' – Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

When a Section 351 exchange can help diversify concentrated stock positions without an immediate tax bill.
The core eligibility rules (80% control test) and basis/step-up mechanics that drive tax deferral.
Sample case studies (James & Sarah) illustrating the numbers and outcomes.

The Strategic Potential of Section 351: An Analysis of a Multi-Stock Case in Tax-Deferred Reorganization

A sizable amount of the wealth of many high-earning professionals at Windstream Holdings may be invested in a small number of highly valued equities, including company shares accumulated through restricted stock units (RSUs), the employee stock purchase plan (ESPP), or equity awards earned due to long tenure. While rebalancing may seem out of reach due to the tax ramifications of selling these positions, investors can make tax-deferred contributions of appreciated assets to a new business entity through a Section 351 exchange. When an investor wants to manage several sizable, embedded gains at once, this tactic may be especially useful.

Think about James, a client with a $10 million portfolio. The value of one stock investment, which he purchased for $50,000, has increased to $1 million, or 10% of his total portfolio. At a long-term capital gains rate that can reach 23.8% for certain high-income taxpayers (20% maximum long-term capital gains rate plus the 3.8% Net Investment Income Tax), selling this position would result in a $950,000 capital gain and an estimated $226,100 tax bill. The amount available for reinvestment would be reduced by this tax.

Section 351(a) of the Internal Revenue Code provides: “If property is transferred to a corporation by one or more persons solely in exchange for stock in such corporation and immediately after the exchange such person or persons are in control (as defined in section 368(c)) of the corporation, no gain or loss shall be recognized.” Under Section 368(c), “control” generally means ownership of at least 80% of the voting power and 80% of each class of non-voting shares.

The transferor or transferors must own at least 80% of the new corporation’s stock right after the exchange to qualify for this treatment. This can be done for investors with sizable portfolios by joining a larger seeding group or acting as the principal seeder of a new entity.

In a Section 351 transaction, any built-in gains are preserved because the shareholder’s basis in the received stock typically carries over from the contributed property. If the shares are held until death, a step-up in basis under Section 1014 may eliminate the deferred gain.

Another client example involves Sarah, who has a $13 million portfolio. She owns two appreciated stocks:

Stock A: Originally $300,000, now worth $3 million.
Stock B: Initial cost basis $500,000, now worth $3 million.

At a long-term capital gains rate that can reach 23.8% for certain high-income taxpayers, the aggregate unrealized gain of $5.2 million would translate into an estimated tax of roughly $1,237,600 if sold today, which can constrain portfolio adjustments.

For employees of Windstream Holdings holding concentrated positions, taking part in a Section 351 exchange can reduce concentration risk and defer recognition of these gains without an immediate tax bill. If assets receive a step-up in basis at death, the deferred gain may be fully eliminated under current law, and deferral can provide flexibility in managing future tax obligations.

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Sources:

1. Internal Revenue Service. Revenue Ruling 2003-51 . Internal Revenue Bulletin 2003-21, 2003. PDF.

2. Friedel, David B., and Yaw O. Awuah. “ Sec. 351 Control Requirement: Opportunities and Pitfalls .” The Tax Adviser , 1 July 2014. Web.

3. Internal Revenue Service. “ Net Investment Income Tax (NIIT) .” IRS.gov , last reviewed 1 July 2025. Web.

4. Internal Revenue Service. Publication 551: Basis of Assets . December 2024 revision, posted 18 February 2025. PDF.

5. FINRA Investor Education Foundation (FINRA). “ Concentrate on Concentration Risk .” FINRA.org , 15 June 2022. Web.

What are the implications of the Windstream Pension Plan for employees who wish to retire early, specifically regarding the eligibility criteria and benefit calculations that will affect their financial planning? How does Windstream address concerns for employees who may be contemplating retirement before reaching the defined Normal Retirement Age of 65?

Early Retirement and Financial Planning: Employees may retire early at age 55 with 20 or more years of service, though the pension benefit will be reduced. The reduction is by 1/180th for the first 60 months and 1/360th for each of the next 60 months that commencement precedes the normal retirement date of age 65. This ensures early retirees can still receive benefits, though at a lower amount than if they had waited until age 65(Windstream_Pension_Plan…).

In what ways does the Windstream Pension Plan protect the interests of employees during a potential plan termination? Specifically, how does the plan ensure that accrued benefits are preserved and what procedures are in place to inform employees about their rights under the Employee Retirement Income Security Act of 1974 (ERISA)?

Plan Termination Protections: In the event of plan termination, Windstream ensures all accrued pensions are fully vested. The plan assets will be used exclusively to meet accrued pension obligations before any surplus may revert to the company. Participants are also protected by the Pension Benefit Guaranty Corporation (PBGC), which guarantees most pension benefits(Windstream_Pension_Plan…).

How does Windstream determine the necessary contributions to the Pension Plan, and what role does an independent actuarial assessment play in this process? Additionally, how does this funding approach impact the overall financial stability of the Windstream Pension Plan and the benefits it promises to its participants?

Contribution Determination and Actuarial Role: Windstream’s contributions to the pension plan are determined by an independent actuary who evaluates the plan annually to recommend adjustments based on experience. This approach ensures that the plan remains financially stable and capable of meeting its promised benefits(Windstream_Pension_Plan…).

What options are available to employees of Windstream regarding the forms of pension benefit payouts upon retirement, and how do these options like the Joint and Survivor Annuities differ in terms of financial implications for both the retiring employee and their spouse?

Benefit Payout Options: Windstream offers several pension payout options, including Joint and 100% Survivor Annuity, Joint and 50% Survivor Annuity, and a 10-Year Certain and Life Annuity. These options differ in terms of the benefit reduction applied to ensure payments continue for the life of the spouse, impacting both the retiree’s and the spouse’s financial planning(Windstream_Pension_Plan…).

How should Windstream employees approach the process of claiming pension benefits, especially if their claims have been denied? What recourse is available for employees who are facing issues with their pension claim and wish to understand their rights and the appeal process?

Claiming Pension Benefits and Denied Claims: If an employee's pension claim is denied, they will receive a written notice explaining the reasons for the denial and the specific plan provisions involved. Employees may appeal the decision within 60 days, and the appeal process must be completed within 60 days of the request, with the right to file a civil lawsuit if necessary(Windstream_Pension_Plan…).

Given the frozen status of the Windstream Pension Plan, what should employees understand about their service years and how these years contribute to their pension benefits? How does Windstream communicate these rules to ensure clarity among its employees?

Service Years and Frozen Status: Since the Windstream Pension Plan is frozen, no additional benefits accrue after December 31, 2007. However, employees continue to earn years of service, which count toward eligibility for early retirement and vesting. Windstream provides clear communication through its summary plan description and resources to ensure employees understand these rules(Windstream_Pension_Plan…).

What strategies can Windstream employees employ to maximize their pension benefits and ensure they are making informed decisions about their retirement? How does Windstream support its employees in accessing the necessary resources and information to facilitate effective retirement planning?

Maximizing Pension Benefits: Employees are encouraged to consider their timing of retirement carefully, as delaying retirement closer to the normal retirement age of 65 reduces benefit reductions. Windstream supports retirement planning through its pension resources and access to Merrill Service Representatives who can assist with planning tools(Windstream_Pension_Plan…).

How does Windstream ensure that employees are aware of their obligations under the plan regarding the filing of claims and maintaining updated personal information? What measures does the company take to keep communication channels open for any inquiries or updates employees might need?

Maintaining Updated Information: Windstream emphasizes the importance of keeping personal information up to date, including changes to contact information. Employees are responsible for filing claims in a timely manner, and failure to do so may result in delays or forfeiture of benefits(Windstream_Pension_Plan…).

In the event of the death of a vested Windstream employee, what benefits are guaranteed to eligible spouses under the plan, and how do survivors initiate the process for claiming these benefits? What steps should surviving spouses take to ensure they receive the necessary support and information from Windstream?

Survivor Benefits and Claim Process: In the event of the death of a vested employee, the spouse is entitled to receive a pre-retirement survivor annuity, which may start on or after the employee’s earliest retirement age. The spouse must contact Windstream to initiate the claim process and may receive a lump sum if the benefit’s present value is below certain thresholds(Windstream_Pension_Plan…).

How can Windstream employees reach out to the companyâ€™s Benefits Committee or Plan Administrator for detailed inquiries about their pension benefits? What contact methods are available, and what information should employees prepare to facilitate effective communication regarding their pension inquiries? These questions will help employees navigate the complexities of the Windstream Pension Plan and ensure they are well-informed as they approach retirement.

Reaching the Benefits Committee: Windstream employees can contact the Benefits Committee or Plan Administrator at Windstream Services, LLC in Little Rock, Arkansas, or via the Merrill Service Center at 1-800-228-4015. Employees should have relevant information, such as personal and employment details, ready to facilitate efficient communication(Windstream_Pension_Plan…).