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Alaska Air Group Employees: Smarter Ways to Manage Taxes on Appreciated Stock

Healthcare Provider Update: Healthcare Provider for Alaska Air Group Alaska Air Group employees primarily receive their health insurance coverage through Premera Blue Cross Blue Shield of Alaska. Premera is the largest insurer in the state and offers various health plan options primarily through the individual marketplace. Potential Healthcare Cost Increases in 2026 As 2026 approaches, Alaska Air Group employees may experience significant increases in healthcare costs, driven by a confluence of factors. Without the continuation of enhanced federal premium subsidies, many individuals could face out-of-pocket premium rises of over 75%. The pressure on employers to shift more health expenses to employees is evident, with a recent survey indicating that 51% of large employers are likely to raise deductibles or out-of-pocket maximums. Coupled with broader trends of medical cost inflation and substantial rate increases requested by insurers, employees of Alaska Air Group should brace for potentially heightened financial burdens in their healthcare coverage. Click here to learn more

'Alaska Air Group 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.

'Alaska Air Group 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.' Alaska Air Group 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. Alaska Air Group 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 Alaska Air Group 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 Alaska Air Group 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 Alaska Air Group 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 Alaska Air Group 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 Alaska Air Group 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 Alaska Air Group 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 type of retirement savings plan does Alaska Air Group offer to its employees?

Alaska Air Group offers a 401(k) retirement savings plan to help employees save for their future.

Does Alaska Air Group match employee contributions to the 401(k) plan?

Yes, Alaska Air Group provides a matching contribution to employee 401(k) accounts, subject to certain limits.

What is the eligibility requirement for Alaska Air Group employees to participate in the 401(k) plan?

Employees of Alaska Air Group are generally eligible to participate in the 401(k) plan after completing a specific period of service, typically within their first year of employment.

Can Alaska Air Group employees choose how much to contribute to their 401(k) plan?

Yes, employees at Alaska Air Group can choose to contribute a percentage of their salary to their 401(k) plan, within the IRS contribution limits.

Are there investment options available for Alaska Air Group employees within the 401(k) plan?

Yes, Alaska Air Group offers a variety of investment options within the 401(k) plan, including mutual funds and other investment vehicles.

How often can Alaska Air Group employees change their 401(k) contribution amounts?

Employees at Alaska Air Group can change their contribution amounts during designated enrollment periods or at specific times throughout the year.

Does Alaska Air Group allow employees to take loans against their 401(k) savings?

Yes, Alaska Air Group allows employees to take loans against their 401(k) savings, subject to the plan’s terms and conditions.

What happens to an Alaska Air Group employee's 401(k) account if they leave the company?

If an Alaska Air Group employee leaves the company, they can choose to roll over their 401(k) balance to another retirement account or cash out, subject to taxes and penalties.

Is there a vesting schedule for the employer match in the Alaska Air Group 401(k) plan?

Yes, Alaska Air Group has a vesting schedule for the employer match, meaning employees must work for a certain period before they fully own the matched funds.

Can Alaska Air Group employees access their 401(k) savings before retirement?

Yes, employees at Alaska Air Group may access their 401(k) savings before retirement under certain circumstances, such as financial hardship or qualifying events.

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

Alaska Air Group has announced a reduction in its workforce by 10% as part of a broader restructuring plan aimed at streamlining operations and cutting costs. This move includes a restructuring of employee benefits and changes to their pension plan.

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For more information you can reach the plan administrator for Alaska Air Group at 19300 International Boulevard Seattle, WA 98188; or by calling them at (206) 433-3200.