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Chesapeake Energy Employees: Smarter Ways to Manage Taxes on Appreciated Stock

Healthcare Provider Update: Healthcare Provider for Chesapeake Energy: Chesapeake Energy utilizes a variety of healthcare providers for its employees, primarily partnering with Blue Cross Blue Shield (BCBS) for health insurance coverage. This long-standing relationship allows Chesapeake Energy to offer a comprehensive benefits package that facilitates access to necessary medical services for its workforce. Potential Healthcare Cost Increases in 2026: As we look towards 2026, Chesapeake Energy employees may face significant healthcare cost increases attributed to anticipated rate hikes within the Affordable Care Act (ACA) marketplace. Premiums are projected to rise dramatically, with reports indicating potential average increases of around 20%, and in some states, even exceeding 60%. The looming expiration of enhanced federal premium subsidies is a critical factor, as it could lead to out-of-pocket premium costs surging by over 75% for the majority of policyholders. This combination of rising medical costs and subsidy reductions will require careful planning from both the company and its employees to manage the impending financial impact effectively. Click here to learn more

'Chesapeake Energy employees with concentrated stock positions may benefit from thoughtful tax planning that allows for tax deferral while balancing liquidity, compliance, and long-term compounding,' Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

'Chesapeake Energy employees who hold highly-appreciated stock may want to consider tax-efficient strategies that help mitigate their liabilities while aligning with their overall retirement goals,' Patrick Ray, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

How taxes can affect investment returns, particularly on concentrated stock positions.
Exchange funds and options-based strategies as methods for tax deferral and diversification.
Alternative planning techniques outside ETFs, including charitable trusts and gifting strategies.

By Carlos Hernandez, Wealth Enhancement advisor

When it comes to driving portfolio returns, many investors aim to keep management fees low by investing in low-cost index funds and exchange-traded funds (ETFs). While fees matter, however, the real culprit for lower-than-anticipated performance is taxes. ¹

Wealth Enhancement advisor Carlos Hernandez explains: 'By losing less to taxes each year, investors have access to more capital that can continue to compound over time. This makes tax deferral an important part of an effective financial plan.' Chesapeake Energy employees looking for long-term growth strategies could benefit by understanding how to better manage their investment tax burdens.

Trade Money

One area where taxes can take a toll is on the sale of company stock or other concentrated investment positions. Chesapeake Energy professionals looking to diversify could face significant capital gains taxes on an outright sale. One way to diversify without triggering immediate capital gains is through exchange funds. By contributing their highy-appreciated stock to a pooled fund, investors can trade their concentrated holdings for shares in a diverse basket of securities. This method can be used by Chesapeake Energy employees who want to diversify while postponing taxable events.

Although this method allows for tax deferral, it also requires investors to hold the exchange fund for a period of time, typically seven years. ² This could create a challenge for investors who require liquidity. Additionally, these funds are often exclusively accessible to wealthy, accredited investors—something Chesapeake Energy executives should carefully evaluate.

Funds Based on Options

Another way to mitigate taxes on the sale of highly-appreciated stock is by using options contracts. The idea is to hedge risk with put options while covering the cost of those puts by selling call options—a strategy called 'collaring'. From there, the strategy reverses, with investors selling put options and using the proceeds to buy call option on an equity or bond index. ³ If managed effectively, this helps to diversify a concentrated portfolio while still maintaining liquidity.

Given the complexity of this strategy, meticulous planning is necessary. It's generally recommended that investors work with an experienced financial advisor before pursuing this approach.

Things to Be Aware of

Although these strategies can be beneficial for Chesapeake Energy employees who hold highly-appreciated stock, caution is recommended. There are costs associated with these approaches, and potential liquidity risks. Additionally, the IRS may eventually contest such arrangements because their tax status has not been thoroughly examined—something Chesapeake Energy retirees should keep top of mind.

'Tax drag reduction strategies can be effective, but they must be assessed through the lens of risk, liquidity, cost, and compliance,' warns Carlos Hernandez. What is appealing in theory must hold up to inspection in the real world.

Alternative Strategies

Although they show promise, investors with highly-appreciated stock or those looking to postpone gains have other alternatives besides exchange funds or options. Other tactics could include:

- Prepaid variable forwards (subject to IRS regulations, contracts to sell at predetermined terms in the future).
- Charitable remainder trusts (CRTs), which allow investors to donate appreciated stock to a charitable trust and receive a stream of regular income in return.
- Donor-advised funds (DAFs), which provide investors with a tax deduction for the fair market value of the appreciated stock they donate.
- Other gifting techniques, such as direct donations to charity or family.
Each has its own set of guidelines, advantages, and disadvantages. To limit unnecessary taxes or violating the constructive sale regulations, careful planning is necessary for Chesapeake Energy professionals managing complex portfolios.

The Bottom Line

Although the movement to mitigate the tax burden on investments is not new, the instruments are changing. Both exchange funds and options-based structures offer investors a way to manage tax liabilities, especially for Chesapeake Energy employees who hold highly-appreciated stock.

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In the end, taxes are unavoidable. However, with the correct set of instruments, they can be controlled and postponed. 'The real value comes from aligning tax strategy with investment strategy,' summarizes Carlos Hernandez.

Sources:

1. BlackRock Advisor Center. ' Investing for After-Tax Returns ,' 2025.

2. Kiplinger. ' Four Clever and Tax-Efficient Ways to Ditch Concentrated Stock Holdings ,' by Robert Waskiewicz. Sep. 11, 2025.

3. Financial Planning Association. ' Tax-Efficient Ways to Diversify Concentrated Stock Positions ,' by Peter Lazaroff. Oct. 2024.

What is the purpose of the 401(k) plan offered by Chesapeake Energy?

The purpose of the 401(k) plan at Chesapeake Energy is to help employees save for retirement by allowing them to contribute a portion of their salary on a pre-tax basis.

How can employees enroll in the Chesapeake Energy 401(k) plan?

Employees can enroll in the Chesapeake Energy 401(k) plan by accessing the company’s benefits portal and following the enrollment instructions provided.

Does Chesapeake Energy offer a company match for 401(k) contributions?

Yes, Chesapeake Energy offers a company match for employee contributions to the 401(k) plan, which helps to enhance retirement savings.

What types of investment options are available in the Chesapeake Energy 401(k) plan?

The Chesapeake Energy 401(k) plan offers a variety of investment options, including mutual funds, stocks, and bonds, allowing employees to choose based on their risk tolerance.

At what age can employees start withdrawing from their Chesapeake Energy 401(k) plan without penalties?

Employees can start withdrawing from their Chesapeake Energy 401(k) plan without penalties at age 59½, subject to certain conditions.

Can employees take loans against their Chesapeake Energy 401(k) plan?

Yes, employees may have the option to take loans against their Chesapeake Energy 401(k) plan, subject to the plan's specific rules and limits.

What happens to the 401(k) plan if an employee leaves Chesapeake Energy?

If an employee leaves Chesapeake Energy, they can choose to roll over their 401(k) balance into another retirement account, leave it in the Chesapeake plan, or cash it out, subject to taxes and penalties.

Is there a vesting schedule for the company match in the Chesapeake Energy 401(k) plan?

Yes, Chesapeake Energy has a vesting schedule for the company match, meaning employees must work for a certain period before they fully own the matched funds.

How often can employees change their contribution amounts to the Chesapeake Energy 401(k) plan?

Employees can typically change their contribution amounts to the Chesapeake Energy 401(k) plan at any time, subject to plan rules and payroll processing schedules.

What is the maximum contribution limit for the Chesapeake Energy 401(k) plan?

The maximum contribution limit for the Chesapeake Energy 401(k) plan is determined by IRS regulations, which may change annually; employees should check the latest limits for accuracy.

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.

In 2024, Chesapeake Energy announced a significant restructuring effort, including a reduction in workforce and changes to its pension plan. The company is focusing on streamlining operations to adapt to fluctuating energy prices and reduce operational costs. Benefits and 401(k) plans are also being evaluated for adjustments to ensure financial stability.

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For more information you can reach the plan administrator for Chesapeake Energy at 6100 N. Western Ave. Oklahoma City, OK 73118; or by calling them at 1-405-848-8000.