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American Express Employees: Smarter Ways to Manage Taxes on Appreciated Stock

Healthcare Provider Update: Healthcare Provider for American Express American Express employees typically receive healthcare benefits through their employer-sponsored health plans rather than the individual marketplace. The company's health insurance offerings are generally provided through major insurers, with options varying by location and employee needs. It is essential for employees to review their specific plan details to understand coverage and benefits. Potential Healthcare Cost Increases for 2026 In 2026, health insurance premiums for plans purchased through the Affordable Care Act (ACA) marketplace are poised for significant increases, with some states reporting hikes of over 60%. A perfect storm of factors is driving this surge, including expiring enhanced federal premium subsidies and soaring medical costs. If these subsidies aren't renewed, a considerable majority of marketplace enrollees could face out-of-pocket premium increases exceeding 75%. This financial pressure will likely push many individuals and families, particularly those reliant on ACA coverage, to reassess their healthcare options and explore alternative strategies to manage costs effectively Click here to learn more

'American Express 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.

'American Express 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.' American Express 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. American Express 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 American Express 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 American Express 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 American Express 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 American Express 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 American Express 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 American Express 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.

How does American Express ensure the adequacy of retiree medical coverage options for employees, especially in aligning with the current healthcare needs specific to its retirees? What factors does American Express consider when determining if changes to the retiree medical plan are necessary, particularly concerning federal and state regulations?

Comparison of American Airlines' 401(k) Plan to Others in the Airline Industry: American Airlines' Super Saver 401(k) plan typically includes employer matching contributions and a variety of investment options, which is common across major airlines. However, the specific matching percentages and investment fund choices may vary, so it's important for employees to compare these details to other airlines to determine where they can maximize their benefits.

In what circumstances can employees of American Express change or cancel their retiree medical coverage? What procedures does American Express recommend to ensure that changes in status or eligibility do not result in gaps in health insurance coverage?

Historical Changes After Bankruptcy: Employees should note that after American Airlines’ Chapter 11 bankruptcy filing, there may have been changes to retirement plans, such as revised matching contribution rates or plan restructuring. Current employees need to understand how these changes affect their retirement savings and future benefits.

As American Express continues to evolve its healthcare offerings, how does the company assess employee satisfaction regarding retiree medical plan options? What mechanisms does American Express use to gather feedback from retirees about their medical plans, and how does this feedback inform future plan design?

Financial Planning Resources: American Airlines probably offers resources like financial counseling, retirement calculators, and online planning tools to help employees assess their retirement readiness. Employees can access these resources through HR or their benefits portal to make informed decisions about their future.

What should American Express retirees know about their rights under ERISA concerning their retiree medical benefits? How does American Express communicate these rights to its employees to ensure awareness and understanding during the transition to retirement?

Maximizing Contributions: Employees should ensure they contribute the maximum allowable by the IRS, currently $22,500 per year (2024 limit), or $30,000 if age 50 or older, to maximize their tax benefits and company match. Understanding the annual contribution limits helps employees avoid over-contributing while still taking full advantage of their plan.

How can employees of American Express contact the company for more information regarding their retiree medical plan options? What specific resources or contact points does American Express offer for retirees seeking detailed guidance on medical benefits?

Contacting HR or Benefits Administration: Employees can typically contact American Airlines’ HR or benefits administration through a dedicated helpline or online portal to inquire about the Super Saver 401(k) plan or other retirement-related concerns. Timely communication ensures employees receive the assistance needed for a smooth retirement process.

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

American Express offers a Defined Benefit Pension Plan and a 401(k) plan with company match. The pension plan provides a monthly retirement benefit based on years of service and salary. The 401(k) plan includes various investment options and financial planning resources.

American Express announced a restructuring plan in 2024 involving significant layoffs and changes to employee benefits. The company aims to streamline operations and cut costs in response to economic pressures. The restructuring includes adjustments to pension and 401(k) plans, focusing on reducing long-term liabilities.

American Express provides RSUs to its executives and key employees. RSUs typically vest over a three to four-year period, promoting long-term goals and company loyalty.

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For more information you can reach the plan administrator for American Express at 200 Vesey Street New York, NY 10285; or by calling them at (212) 640-2000.