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Arthur J. Gallagher Employees: Smarter Ways to Manage Taxes on Appreciated Stock

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'Arthur J. Gallagher 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.

'Arthur J. Gallagher 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.' Arthur J. Gallagher 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. Arthur J. Gallagher 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 Arthur J. Gallagher 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 Arthur J. Gallagher 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 Arthur J. Gallagher 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 Arthur J. Gallagher 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 Arthur J. Gallagher 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 Arthur J. Gallagher 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.

How can Gallagher, Flynn & Company LLP assist employees in understanding the advantages and disadvantages of cash balance retirement plans compared to traditional pension plans, and what factors should employees consider when determining which plan might be more beneficial for their unique financial situations within Gallagher, Flynn & Company LLP?

Understanding the advantages and disadvantages of cash balance plans: Gallagher, Flynn & Company LLP helps employees understand the benefits of cash balance retirement plans by comparing them to traditional pension plans. Cash balance plans offer higher contribution limits and more retirement savings while also reducing tax liability. However, employees must consider that cash balance plans distribute benefits evenly across all working years, which could lead to lower benefits than traditional pension plans that focus on the highest earning years​(Gallagher_Flynn_Company…).

As an employee of Gallagher, Flynn & Company LLP, what specific criteria should individuals meet to be eligible for participation in a cash balance retirement plan, and how does Gallagher, Flynn & Company LLP ensure compliance with these criteria to maintain the plan’s integrity?

Eligibility for participation in a cash balance plan: Employees at Gallagher, Flynn & Company LLP must meet specific criteria to participate in cash balance retirement plans. These criteria typically involve employer contributions of 5-8% of the employee's salary. The company ensures compliance with contribution regulations by maintaining consistent cash flow to meet the annual contribution requirements​(Gallagher_Flynn_Company…).

What are the current IRS contribution limits for cash balance retirement plans in 2024, and how does Gallagher, Flynn & Company LLP implement these limits to maximize the retirement savings of its employees, particularly those nearing retirement age or with higher incomes?

IRS contribution limits in 2024: The IRS contribution limit for cash balance plans in 2024 is over $200,000 for participants aged 60 or over. Gallagher, Flynn & Company LLP implements these limits by allowing employees to contribute significant amounts, especially those nearing retirement, helping them maximize their retirement savings while reducing their tax burden​(Gallagher_Flynn_Company…).

In what ways can employees of Gallagher, Flynn & Company LLP expect their retirement benefits to be calculated under a cash balance pension plan, and how do the different factors affecting this calculation impact long-term financial planning for employees?

Retirement benefits calculation under a cash balance plan: Retirement benefits in a cash balance plan at Gallagher, Flynn & Company LLP are calculated based on the percentage of the employee’s salary credited to their account each year, plus an interest credit. This structure allows employees to plan for long-term financial stability, although it may result in lower overall retirement benefits compared to traditional pension plans due to the even distribution of contributions​(Gallagher_Flynn_Company…).

What steps does Gallagher, Flynn & Company LLP take to communicate updates or changes in cash balance retirement plan regulations, and how can employees stay informed about their rights and obligations under these plans?

Communication about plan updates: Gallagher, Flynn & Company LLP regularly communicates updates and changes in cash balance retirement plan regulations through company-wide communications and financial advising services. Employees are encouraged to stay informed by contacting the company’s financial advisors or reviewing regulatory updates to understand their rights and obligations​(Gallagher_Flynn_Company…).

Can you elaborate on the specific tax benefits associated with cash balance retirement plans that are offered by Gallagher, Flynn & Company LLP, and how these benefits compare to those available through other retirement plans?

Tax benefits of cash balance plans: Cash balance retirement plans at Gallagher, Flynn & Company LLP offer significant tax benefits by allowing for higher contribution limits than traditional 401(k) plans. These higher limits enable employees to lower their taxable income, making these plans advantageous for employees seeking to minimize tax liabilities and increase retirement savings​(Gallagher_Flynn_Company…).

How does Gallagher, Flynn & Company LLP support employees who are considering transitioning from a traditional pension plan to a cash balance retirement plan, and what resources are available to facilitate this decision-making process?

Support for transitioning to a cash balance plan: Gallagher, Flynn & Company LLP provides resources and personalized financial advising to employees considering a transition from a traditional pension plan to a cash balance plan. The company ensures that employees understand the benefits and limitations of both plans, offering guidance to facilitate informed decisions​(Gallagher_Flynn_Company…).

What strategies does Gallagher, Flynn & Company LLP recommend to employees who are in a position to "catch up" on their retirement contributions, particularly for those over the age of 40, to take full advantage of the higher limits associated with cash balance retirement plans?

Catch-up contributions: Employees over 40 at Gallagher, Flynn & Company LLP can take advantage of catch-up contributions due to the higher contribution limits of cash balance plans. The company recommends that older employees maximize these contributions to enhance their retirement savings and benefit from the associated tax advantages​(Gallagher_Flynn_Company…).

How does Gallagher, Flynn & Company LLP determine the annual employer contribution rates for its cash balance retirement plan, and what factors influence the sustainability of these contributions in the long-term financial health of the company and its employees?

Annual employer contribution rates: Gallagher, Flynn & Company LLP determines the employer contribution rates for cash balance plans based on a percentage of employee salaries, typically ranging from 5-8%. These contributions are influenced by the company’s financial stability and commitment to providing robust retirement benefits for long-term employee financial health​(Gallagher_Flynn_Company…).

If an employee at Gallagher, Flynn & Company LLP has additional questions about the cash balance retirement plans and needs further assistance, what are the best ways for them to contact Gallagher, Flynn & Company LLP to receive tailored guidance or information?

Contact for further assistance: Employees at Gallagher, Flynn & Company LLP who have additional questions about the cash balance retirement plans can contact the company through their financial advisors or reach out to their local offices for tailored guidance and support. The company’s financial team is available to provide personalized information and assistance as needed​(Gallagher_Flynn_Company…).

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.
Arthur J. Gallagher recently announced a series of restructuring efforts aimed at streamlining operations and improving efficiency. This includes significant layoffs and changes to employee benefits. Given the current economic volatility and the evolving tax and investment climate, it is crucial to stay informed about these developments to navigate potential impacts on retirement planning and investment strategies.
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For more information you can reach the plan administrator for Arthur J. Gallagher at 2850 Golf Rd Rolling Meadows, IL 60008; or by calling them at +1 847-953-3000.

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