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CSX Employees: Smarter Ways to Manage Taxes on Appreciated Stock

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Healthcare Provider Update: Healthcare Provider for CSX: CSX Corporation has partnered with Aetna, a division of CVS Health, to provide healthcare benefits for its employees. This collaboration allows CSX employees access to a wide range of health services and insurance plans tailored to meet their specific needs. Potential Healthcare Cost Increases in 2026: In 2026, CSX and its employees may face significant healthcare cost challenges, as the landscape for health insurance is set to experience considerable changes. With proposed premium hikes in the Affordable Care Act marketplace reaching as much as 66% in some states, the potential expiration of enhanced federal premium subsidies may exacerbate out-of-pocket expenses for many enrollees. A forecast indicates that over 22 million individuals could see their premiums increase by more than 75%, driven by rising medical costs and insurers' aggressive rate adjustments. This surge in costs could create financial strain not only for individual employees but also for the company's overall healthcare budget, necessitating strategic planning and proactive measures for 2026. Click here to learn more

'CSX 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.

'CSX 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:

  1. How taxes can affect investment returns, particularly on concentrated stock positions.

  2. Exchange funds and options-based strategies as methods for tax deferral and diversification.

  3. 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.' CSX 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. CSX 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 CSX 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 CSX 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 CSX 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 CSX 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 CSX 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 CSX 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 purpose of the 401(k) plan at CSX?

The 401(k) plan at CSX is designed to help employees save for retirement by allowing them to contribute a portion of their salary on a pre-tax basis.

How can CSX employees enroll in the 401(k) plan?

CSX employees can enroll in the 401(k) plan through the company’s HR portal or by contacting the HR department for assistance.

Does CSX offer a company match for 401(k) contributions?

Yes, CSX offers a company match for 401(k) contributions, which allows employees to increase their retirement savings.

What is the maximum contribution limit for CSX employees under the 401(k) plan?

The maximum contribution limit for CSX employees under the 401(k) plan is determined by the IRS and may change annually. Employees should check the latest IRS guidelines for the current limit.

Can CSX employees take loans against their 401(k) savings?

Yes, CSX allows employees to take loans against their 401(k) savings, subject to certain conditions and limits outlined in the plan documents.

What investment options are available in CSX's 401(k) plan?

CSX's 401(k) plan offers a variety of investment options, including mutual funds, stocks, and bonds, allowing employees to choose based on their risk tolerance and retirement goals.

When can CSX employees start withdrawing from their 401(k) plan?

CSX employees can start withdrawing from their 401(k) plan at age 59½, or earlier under certain circumstances, such as financial hardship.

Is there a vesting schedule for CSX's 401(k) company match?

Yes, CSX has a vesting schedule for the company match, which means employees must work for a certain period to fully own the matched contributions.

How often can CSX employees change their 401(k) contribution amount?

CSX employees can change their 401(k) contribution amount at any time, subject to the plan's guidelines and payroll processing schedules.

What happens to a CSX employee's 401(k) if they leave the company?

If a CSX employee leaves the company, they can choose to roll over their 401(k) balance to another retirement account, cash out, or leave the funds in the CSX plan if permitted.

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.
The pension plan for CSX employees is part of the Railroad Retirement Act, specifically referred to as the CSX Railroad Retirement plan. Eligibility and Qualifications: Years of Service: Employees typically need to have at least 10 years of service to be eligible for the pension plan benefits. Age Qualification: Full retirement benefits are available at age 60 with 30 years of service or age 62 with fewer years of service. Pension Formula: The pension is calculated based on the highest three earning years. The formula generally provides 80% of the average highest earnings after 30 years of service. Specific Terms and Acronyms: RRB (Railroad Retirement Board): Governs the administration of the railroad retirement benefits. Tier I and Tier II Benefits: Components of the Railroad Retirement benefits, with Tier I similar to Social Security and Tier II providing additional benefits based on railroad earnings. CSX 401(k) Plan: Name of 401(k) Plan: CSX offers the CSXtra 401(k) plan. Eligibility and Qualifications: Who Qualifies: All full-time employees are eligible to participate in the CSXtra 401(k) plan. Contribution Limits: Employees can contribute from 1% to 50% of their eligible pay up to the IRS limits, with additional catch-up contributions for those aged 50 and older. Company Match: CSX matches 100% of the first 1% of the employee's contribution and 50% of the next 5% of the contributions.
Layoffs and Restructuring: CSX has not announced significant layoffs recently but is continuously adjusting its workforce through normal attrition and targeted hiring to meet changing market demands.
2022: In 2022, CSX granted stock options and RSUs to key executives, focusing on aligning their incentives with the company's strategic goals. The grants were part of the annual executive compensation review. 2023: The 2023 program continued to emphasize performance-based RSUs, rewarding employees for meeting specific operational and financial targets. This year's grants included a significant component tied to sustainability and ESG (Environmental, Social, Governance) metrics, reflecting the company's commitment to sustainable growth. 2024: In 2024, CSX expanded its RSU program to include more mid-level management positions, recognizing the broader impact of these roles on company performance. This year’s stock options included features to enhance retention and reward long-term loyalty among employees.
Health Insurance: CSX offers various health insurance plans, including options with low co-pays and comprehensive coverage through Aetna. These plans cover a wide range of medical services and prescriptions. Wellness Programs: To promote physical and mental health, CSX has implemented wellness programs that include health assessments, fitness challenges, and access to wellness resources. Flexible Spending Accounts (FSAs): Employees can set aside pre-tax dollars for healthcare expenses through Health Care FSAs. The contribution limit for 2024 is $3,050, with a carryover limit of $610 from the previous year. Accidental Death and Dismemberment (AD&D) Insurance: CSX provides AD&D insurance, which covers employees in case of serious injuries or death due to accidents, with various coverage options based on annual pay. Recent Employee Healthcare News: In recent years, CSX has maintained stable health insurance premiums while enhancing the benefits package to meet evolving needs. The company continues to focus on offering competitive and comprehensive health benefits to attract and retain top talent. For instance, CSX has been recognized for its support of military and first responders through its Pride in Service program, which also contributes to the overall health and wellness of its employees.
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For more information you can reach the plan administrator for CSX at 500 Water St Jacksonville, FL 32202; or by calling them at (904) 359-3200.

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