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American Express Employees: Strategic Ways to Reduce Capital Gains 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 can benefit from understanding that strategies like a Section 351 exchange, charitable donations, and tax loss harvesting may work together to help manage appreciated stock efficiently while aligning with broader long-term financial goals.' – Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.

'American Express employees should recognize that thoughtful planning with tools such as Section 351 exchanges, gifting strategies, and tax loss harvesting can help them manage highly appreciated stock while supporting both personal and philanthropic objectives.' – Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

How a Section 351 exchange can defer capital gains on highly appreciated stock.
Alternative tax-efficient strategies such as charitable donations, tax loss harvesting, and gifting.
The role of inheritance rules, step-up in basis, and combined approaches in long-term tax planning.

A Tax-Aware Q&A on How to Manage Highly Appreciated Stock

From the Section 351 exchange to other practical approaches, this Q&A addresses key considerations American Express employees may encounter when dealing with highly appreciated shares.

Section 351 Exchange: The Fundamental Approach

Q: What is an exchange under Section 351?
A: Under certain circumstances, an investor may transfer property, such as highly appreciated shares, to a company in exchange for its stock under a provision of the Internal Revenue Code that allows the deferral of capital gains or losses.

Q: What is the primary advantage of exchanging my appreciated stock through a Section 351 exchange?
A: The main advantage is tax deferral. Gains transferred to corporations may be postponed under Section 351, though this applies only if specific diversification requirements are met, especially when transferring to investment companies like exchange-traded funds (ETFs). ¹

Q: What is meant by the “Control Test”?
A: The investor or group of investors who use their portfolio assets to fund the new entity must own at least 80% of the voting power and 80% of the total number of shares of all other classes of stock in the new company immediately after the exchange. ¹

Q: When seeding an ETF, how is the Control Test usually satisfied?
A: It is typically satisfied by either a single substantial investor making a significant asset contribution or multiple investors pooling assets to create a seeding pool for the ETF’s launch.

Q: What is the ultimate tax payment date for the deferred gain?
A: The deferred gain is recognized when the ETF shares acquired through the exchange are sold; distributions from taxable funds must also be reported in the meantime.

Other Tax-Efficient Techniques

Q: What is a straightforward method, aside from a Section 351 exchange, to sell highly appreciated shares without incurring large taxes?
A: Donating shares directly to a qualified charity is one option that some American Express employees may benefit from.

Q: What tax advantages come with donating valuable stock to a charity?
A: Subject to holding period and adjusted gross income (AGI) limits, you can bypass capital gains taxes on the appreciation and may receive an income tax deduction for the stock’s full fair market value.

Q: What is a Donor-Advised Fund (DAF)?
A: A DAF allows you to donate appreciated stock, receive an immediate tax deduction, and then recommend grants to charities over time, while the assets in the DAF grow without tax impact. ²

Q: Can I give a family member my appreciated stock as a gift?
A: Yes. In most cases, the cost basis from the donor carries over to the recipient.

Q: Why would I give a family member in a lower tax bracket appreciated stock?
A: If they sell the stock, the lower income could result in a reduced capital gains rate, potentially as low as 0% for long-term gains. ³

Tax Loss Harvesting and Other Approaches

Q: What is harvesting tax losses?
A: Selling investments at a loss to offset gains from other sales is known as tax loss harvesting, a strategy sometimes considered by American Express employees seeking opportunities to leverage bouts of market volatility.

Q: Can I deduct a certain amount of loss from my regular income?
A: Yes. If your capital losses exceed your gains, you can use up to $3,000 per year ($1,500 if married filing separately) to offset ordinary income, with remaining losses carried forward indefinitely. ⁴

Q: What is a Qualified Opportunity Fund (QOF)?
A: A QOF provides investors with tax incentives for investing in tracts of land designated as 'opportunity zones'. Capital gains reinvested in a QOF within 180 days of being realized can be temporarily tax deferred, while QOF investments helpd for at least 10 years may confer a permanent capital gains exclusion. ⁵ That said, 2025 legislation changes may prompt IRS updates to this rule.

Inheritance and Step-Up in Basis

Q: What is meant by a “step-up in basis”?
A: This adjusts an inherited asset’s cost basis to its fair market value at the time of the owner’s death, eliminating capital gains accumulated during their lifetime. ⁶

Q: If I gift shares while living, will I receive a step-up in basis?
A: No. The original cost basis transfers to the recipient without adjustment.

Determining the Right Strategy

Q: What is the best course of action for me?
A: The most suitable approach will depend on factors such as your gain size, income level, charitable intentions, and liquidity needs.

Q: Do any of these strategies call for professional guidance?
A: Yes. Given the complexity of the tax code, working with a qualified financial advisor and tax professional is strongly recommended before implementing these strategies.

Q: Is it possible to combine these strategies?
A: Yes. For example, you might execute a Section 351 exchange on part of your portfolio for tax-deferred rebalancing while donating another portion to a DAF for an immediate deduction.

Q: Is there a loophole in the Section 351 exchange?
A: No. This is a legitimate tax code provision designed for corporate restructuring and adapted for use in the ETF market. It is intended for tax deferral, not permanent tax elimination.

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Articles you may find interesting:

Sources:

1. Kitces. ' Using Section 351 Exchanges to Tax-Efficiently Reallocate Portfolios With Embedded Gains ,' by Ben Henry-Moreland and Brent Sullivan. 12 Mar. 2025.

2. Kiplinger. “ A Donor-Advised Fund Can Give Your Charitable Giving a Boost ,” by Samuel Gaeta. 9 May 2024.

3. Internal Revenue Service. “ Topic No. 409, Capital Gains and Losses .” IRS.gov , 8 July 2025.

4. Wealth Enhancement. ' 6 Essential Tax-Loss Harvesting Tips ,' by Jim Wiley. 6 April 2022.

5. Congressional Research Service. ' Tax Incentives for Opportunity Zones ,' by Donald Marples. 26 Apr. 2022.

6. Investopedia. “ Carryover Basis: What It Is, How It Works, Gift Taxes ,” by Julia Kagan. 16 Jan. 2023.

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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.