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Citigroup Employees: Smarter Ways to Manage Taxes on Appreciated Stock

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Healthcare Provider Update: Healthcare Provider for Citigroup: Citigroup's primary healthcare provider is UnitedHealthcare, which offers a range of health insurance products for Citigroup employees, including employer-sponsored plans that provide comprehensive coverage. Potential Healthcare Cost Increases in 2026: As we look ahead to 2026, healthcare costs associated with the Affordable Care Act (ACA) are projected to rise dramatically. With insurers requesting average premium increases of 18% and some states seeing hikes surpassing 60%, millions of consumers could face unprecedented out-of-pocket costs. Key factors driving these increases include the potential expiration of enhanced federal premium subsidies, which could lead to a staggering 75% increase in out-of-pocket premiums for approximately 92% of marketplace enrollees. The combination of escalating medical costs and the withdrawal of financial assistance presents a significant financial challenge for many families across the nation. Click here to learn more

'Citigroup 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.

'Citigroup 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.' Citigroup 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. Citigroup 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 Citigroup 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 Citigroup 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 Citigroup 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 Citigroup 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 Citigroup 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 Citigroup 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 are the main eligibility criteria for participating in the Citigroup Pension Plan, and how can Citigroup employees ensure they meet these requirements throughout their employment? Furthermore, what implications does the merger of prior pension plans into the Citigroup Pension Plan have on the benefits for employees from acquired companies, and what steps should they take to understand how their previous service is credited under Citigroup?

Eligibility Criteria for Citigroup Pension Plan Participation: Employees hired before January 1, 2007, are eligible to participate in the Citigroup Pension Plan if they were employees of a Participating Employer. Employees hired after that date are generally not eligible to participate. Additionally, employees from acquired companies may have their prior service credited under Citigroup. It's important for these employees to review the plan's specific provisions or contact the Citi Pension Center to ensure accurate service credit​(Citigroup_Pension_Plan_…).

How does the Citigroup Pension Plan address survivor benefits for employees who pass away before their pension benefits commence, and what steps must their beneficiaries take to claim these benefits? Additionally, how can employees ensure that their loved ones are adequately informed about the options available should they face this unfortunate event?

Survivor Benefits for Pre-Retirement Death: If an employee passes away before benefits commence, the surviving spouse may receive a lifetime annuity based on the account balance or opt for a lump sum. Employees should ensure that their beneficiaries are aware of these options and the process to claim benefits​(Citigroup_Pension_Plan_…).

For Citigroup employees wanting to learn more about the pension plan's benefits and options available to them, what contact methods should they use? How does Citigroup facilitate communication regarding the pension plan, and what are the most efficient ways for employees to get their questions answered?

Contacting Citigroup for Pension Plan Inquiries: Employees can contact the Citi Pension Center by phone at 1-800-881-3938 for U.S. inquiries or use the online portal to access their pension details. These methods provide the most efficient way to get answers to any pension-related questions​(Citigroup_Pension_Plan_…).

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.
Citigroup offers both a traditional defined benefit pension plan and a defined contribution 401(k) plan. The defined benefit plan provides retirement income based on years of service and final average pay. The 401(k) plan includes company matching contributions and various investment options such as target-date funds and mutual funds. Citigroup also provides financial planning resources and tools to help employees manage their retirement savings.
Citigroup is planning to cut 20,000 jobs as part of a major restructuring effort to streamline operations and save $2.5 billion. The bank is also focusing on international growth and simplifying its management structure from 13 layers to eight. Despite the layoffs, Citigroup continues to offer comprehensive retirement benefits, including 401(k) plans and health benefits. Understanding these benefits is important in today's political environment.
Citigroup grants RSUs that vest over several years, giving employees shares upon vesting. They also provide stock options, allowing employees to purchase shares at a set price.
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For more information you can reach the plan administrator for Citigroup at 388 Greenwich St New York, NY 10013; or by calling them at (212) 559-1000.

*Please see disclaimer for more information

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