<img height="1" width="1" style="display:none" src="https://www.facebook.com/tr?id=314834185700910&amp;ev=PageView&amp;noscript=1">

New Update: Healthcare Costs Increasing by Over 60% in Some States. Will you be impacted?

Learn More

American Express Employees: Handling Single-Stock Concentration with a Section 351 Strategy

image-table

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 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.

'American Express 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:

  1. When a Section 351 exchange can help diversify concentrated stock positions without an immediate tax bill.

  2. The core eligibility rules (80% control test) and basis/step-up mechanics that drive tax deferral.

  3. 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 American Express 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 American Express 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.

Featured Video

Articles you may find interesting:

Loading...

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.

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.
New call-to-action

Additional Articles

Check Out Articles for American Express employees

Loading...

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.

*Please see disclaimer for more information

Relevant Articles

Check Out Articles for American Express employees