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Community Health Systems Employees: Smarter Ways to Manage Taxes on Appreciated Stock

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Healthcare Provider Update: Healthcare Provider for Community Health Systems Community Health Systems, Inc. (CHS) operates as a publicly traded healthcare management company, primarily providing hospital and healthcare services. It manages a network of acute care hospitals and outpatient care facilities across the United States, serving millions of patients annually. Brief on Healthcare Cost Increases in 2026 As we approach 2026, significant healthcare cost increases are anticipated, particularly for those enrolled in Affordable Care Act (ACA) marketplace plans. With projections indicating some states could see premium hikes exceeding 60%, the withdrawal of enhanced federal premium subsidies will likely exacerbate the financial burden on consumers. A recent analysis suggests that without congressional intervention, over 22 million ACA enrollees could face a staggering 75% rise in out-of-pocket premium costs. Factors contributing to this situation include rising medical expenses, increased demand for healthcare services, and the sustained profitability of major insurers amidst substantial rate hikes. Click here to learn more

'Community Health Systems 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.

'Community Health Systems 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.' Community Health Systems 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. Community Health Systems 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 Community Health Systems 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 Community Health Systems 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 Community Health Systems 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 Community Health Systems 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 Community Health Systems 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 Community Health Systems 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 plan does Community Health Systems offer to its employees?

Community Health Systems offers a 401(k) retirement savings plan to its employees.

How can employees of Community Health Systems enroll in the 401(k) plan?

Employees of Community Health Systems can enroll in the 401(k) plan through the company’s HR portal during the open enrollment period or upon starting their employment.

Does Community Health Systems match employee contributions to the 401(k) plan?

Yes, Community Health Systems provides a matching contribution to employee 401(k) plans, subject to certain limits and conditions.

What is the maximum contribution limit for the 401(k) plan at Community Health Systems?

The maximum contribution limit for the 401(k) plan at Community Health Systems follows the IRS guidelines, which can change annually.

Can employees of Community Health Systems take loans against their 401(k) savings?

Yes, Community Health Systems allows employees to take loans against their 401(k) savings, subject to specific terms and conditions.

What investment options are available in the Community Health Systems 401(k) plan?

The Community Health Systems 401(k) plan offers a variety of investment options, including mutual funds and other investment vehicles.

Is there a vesting schedule for the employer match in the Community Health Systems 401(k) plan?

Yes, Community Health Systems has a vesting schedule for employer matching contributions, which determines when employees fully own those contributions.

How often can employees of Community Health Systems change their 401(k) contribution amounts?

Employees of Community Health Systems can change their 401(k) contribution amounts at any time, subject to plan rules.

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

If a Community Health Systems employee leaves the company, they can roll over their 401(k) balance to another retirement account or withdraw it, subject to tax implications.

Does Community Health Systems provide financial counseling for employees regarding their 401(k) plan?

Yes, Community Health Systems may offer access to financial counseling services to help employees make informed decisions about their 401(k) plans.

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.
Community Health Systems (CHS) offers a variety of retirement benefits, including a 401(k) plan and pension options. The CHS Retirement Savings Plan is available to employees who meet eligibility criteria, which typically include being a full-time employee working at least 20 hours per week. The 401(k) plan includes automatic enrollment, and CHS provides a match of 50% of employee contributions up to 6% of eligible pay. Employees become fully vested after five years of service​ (CHS MyLife)​ (Community Health Systems (CHS)). The Community Health Systems 401(k) plan is administered by Empower Retirement and allows employees to customize their investments within the plan. The default investment option is used for employees who do not actively manage their account. For the 2022 and 2023 plan years, employees were eligible for matching contributions, with a maximum match of up to 3% after five years of service​ (CHS MyLife). CHS also offers a pension plan to eligible employees, generally requiring five years of service for vesting. The pension formula is based on a final average pay formula, and specific details about the pension plan, such as the age and service qualifications, are included in the company's Summary Plan Description (SPD), which can be accessed through their benefits portal​
Restructuring & Layoffs: Community Health Systems announced significant restructuring efforts in 2023, which included a reduction of its workforce by approximately 3,000 employees. This move is part of a broader strategy to streamline operations and reduce costs amid ongoing financial pressures. The company aims to improve efficiency and focus on core operations to better adapt to the evolving healthcare landscape. Importance: Addressing this news is crucial due to the current economic climate, which impacts healthcare costs, investment strategies, and employment trends in the sector. Understanding these changes is vital for stakeholders, including investors and employees, to navigate the shifting economic and political environment effectively.
Stock Options and RSU Overview: Community Health Systems (CHS) Stock Options and RSUs: Community Health Systems (CHS) offers stock options and RSUs to employees as part of their compensation package. Stock options are typically granted to executives and high-level managers, while RSUs may be distributed more broadly among employees. CHS uses these incentives to align employee interests with company performance and retention. Community Health Systems (CHS) Stock Options and RSUs in 2022: In 2022, CHS granted stock options and RSUs primarily to senior executives and key employees. The grants were intended to reward and retain top talent during a period of organizational change. The details are documented in the 2022 annual report on page 47. Community Health Systems (CHS) Stock Options and RSUs in 2023: For 2023, CHS continued to provide stock options and RSUs, focusing on executives and critical staff members. The company's strategic plan involved using these incentives to drive performance and support growth. The relevant information is found in the 2023 SEC filing on page 53. Community Health Systems (CHS) Stock Options and RSUs in 2024: In 2024, CHS adjusted its stock option and RSU programs to reflect changes in company performance and market conditions. These adjustments aimed to ensure competitiveness and retention. Details are available in the 2024 compensation report on page 60.
Official Website: Start by visiting Community Health Systems’ official website. Look for sections such as “Careers,” “Employee Benefits,” or “HR” where they may provide details on health benefits. Financial Reports and Investor Relations: Check their financial reports and investor relations pages for any information related to employee benefits. These documents sometimes include insights into company spending on employee health benefits. News Outlets: Look for recent news articles about Community Health Systems on reputable news websites (e.g., Reuters, Bloomberg, CNBC). Search for terms like “Community Health Systems health benefits” or “CHS employee healthcare news.” Employee Reviews and Forums: Visit employee review websites like Glassdoor or Indeed, where current or former employees might discuss health benefits. Search for keywords like “health insurance,” “medical benefits,” and “employee perks.” Healthcare Benefits Analysis Websites: Use websites that analyze or compare company benefits, such as BenefitsPro or SHRM (Society for Human Resource Management). These sites often have articles or reports on company health benefits.
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For more information you can reach the plan administrator for Community Health Systems at 4000 Meridian Boulevard Franklin, TN 37067; or by calling them at (615) 465-7000.

*Please see disclaimer for more information

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