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Delta Air Lines Employees: Smarter Ways to Manage Taxes on Appreciated Stock

Healthcare Provider Update: Healthcare Provider for Delta Air Lines: Delta Air Lines employees typically access healthcare services through a variety of providers. The specific healthcare provider network can vary by plan, but Delta often partners with major health insurance companies such as UnitedHealthcare, Anthem (Elevance Health), and Cigna to offer health benefits to its employees. Brief on Potential Healthcare Cost Increases in 2026: As healthcare costs continue to rise, Delta Air Lines employees should prepare for significant out-of-pocket expenses in 2026. With projections indicating that premiums for Affordable Care Act (ACA) policies could soar by as much as 66% in certain states, nearly 92% of marketplace enrollees could face increases of over 75% due to the expiration of federal subsidies. These factors, combined with rising medical costs and insurer profit pressures, suggest that employees may need to reassess their healthcare plans and budget accordingly, as many companies, including Delta, are likely to pass on more costs to workers. Click here to learn more

'Delta Air Lines 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.

'Delta Air Lines 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.' Delta Air Lines 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. Delta Air Lines 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 Delta Air Lines 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 Delta Air Lines 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 Delta Air Lines 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 Delta Air Lines 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 Delta Air Lines 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 Delta Air Lines 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 401(k) plan offered by Delta Air Lines?

The 401(k) plan offered by Delta Air Lines is a retirement savings plan that allows employees to save a portion of their paycheck before taxes are taken out, helping them prepare for retirement.

How does Delta Air Lines match employee contributions to the 401(k) plan?

Delta Air Lines offers a matching contribution to the 401(k) plan, which typically matches a percentage of the employee's contributions, up to a certain limit.

What are the eligibility requirements to participate in Delta Air Lines' 401(k) plan?

Employees of Delta Air Lines are eligible to participate in the 401(k) plan after completing a specific period of service, which is outlined in the plan details.

Can Delta Air Lines employees change their contribution rates to the 401(k) plan?

Yes, employees at Delta Air Lines can change their contribution rates to the 401(k) plan at any time, subject to the plan's guidelines.

What investment options are available in Delta Air Lines' 401(k) plan?

Delta Air Lines provides a variety of investment options in its 401(k) plan, including mutual funds, target-date funds, and other investment vehicles.

Is there a vesting schedule for the employer match in Delta Air Lines' 401(k) plan?

Yes, Delta Air Lines has a vesting schedule for the employer match, meaning that employees must work for a certain period before they fully own the matched contributions.

How can Delta Air Lines employees access their 401(k) account information?

Delta Air Lines employees can access their 401(k) account information through the company's benefits portal or by contacting the plan administrator.

What happens to my Delta Air Lines 401(k) if I leave the company?

If you leave Delta Air Lines, you have several options for your 401(k), including rolling it over to another retirement account, leaving it with Delta, or cashing it out, subject to taxes and penalties.

Are there loans available against my 401(k) at Delta Air Lines?

Yes, Delta Air Lines allows employees to take loans against their 401(k) balance, subject to the terms and conditions set forth in the plan.

How often can I change my investment allocations in Delta Air Lines' 401(k) plan?

Employees at Delta Air Lines can change their investment allocations in the 401(k) plan as often as they like, following the plan's guidelines.

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

Delta Air Lines provides a defined contribution 401(k) plan with company matching contributions. Employees can contribute pre-tax or Roth (after-tax) dollars, and Delta matches up to 9% of eligible compensation. The plan includes various investment options, such as target-date funds, mutual funds, and a self-directed brokerage account. Delta also offers financial planning resources and tools to help employees manage their retirement savings.

Cummins is implementing layoffs to improve operational efficiencies and meet zero-emission goals. The company has offered voluntary retirement and separation packages to eligible employees and is focused on reducing middle management roles. Despite cost-cutting measures, Cummins continues to offer a comprehensive benefits package including a 401(k) plan. Staying informed about these benefits is crucial given the current political environment

Delta Air Lines provides RSUs that vest over time, giving employees shares of the company upon meeting vesting conditions. Stock options are also available, allowing employees to buy shares at a set price.

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For more information you can reach the plan administrator for Delta Air Lines at 1030 Delta Blvd Atlanta, GA 30320; or by calling them at (404) 715-2600.