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Deere Employees: Smarter Ways to Manage Taxes on Appreciated Stock

Healthcare Provider Update: Healthcare Provider for Deere: Deere & Company, known for its agricultural machinery and equipment, primarily offers healthcare benefits to its employees through a network of health insurance providers. These usually include notable insurers such as UnitedHealthcare, Aetna, and Blue Cross Blue Shield, depending on the specific location and employment agreements. Potential Healthcare Cost Increases in 2026: As we look ahead to 2026, healthcare costs are poised to increase significantly, largely driven by anticipated rate hikes in the Affordable Care Act (ACA) marketplace. Reports indicate that premiums could rise by as much as 75% for a substantial majority of enrollees if enhanced federal premium subsidies expire. Coupled with rising medical service costs and inflation pressures, the ACA's potential median premium increase of 18% could lead many employees and their families, including those at Deere, to face markedly higher healthcare expenses just as the industry grapples with supply chain and labor cost challenges. This situation underscores the urgent need for employee awareness and strategic planning in the upcoming open enrollment periods. Click here to learn more

'Deere 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.

'Deere 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.' Deere 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. Deere 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 Deere 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 Deere 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 Deere 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 Deere 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 Deere 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 Deere 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) Savings Plan at Deere?

The purpose of the 401(k) Savings Plan at Deere is to help employees save for retirement by allowing them to contribute a portion of their salary on a pre-tax or Roth after-tax basis.

How can employees enroll in Deere's 401(k) Savings Plan?

Employees can enroll in Deere's 401(k) Savings Plan by accessing the plan's website or contacting the HR department for enrollment instructions.

What types of contributions can employees make to Deere's 401(k) Savings Plan?

Employees can make pre-tax contributions, Roth after-tax contributions, and, in some cases, catch-up contributions if they are age 50 or older.

Does Deere offer a company match for the 401(k) Savings Plan?

Yes, Deere offers a company match for the 401(k) Savings Plan, which helps employees boost their retirement savings.

What is the vesting schedule for Deere's company match in the 401(k) Savings Plan?

The vesting schedule for Deere's company match varies based on the employee's length of service, and employees should refer to the plan documents for specific details.

Can employees take loans against their 401(k) Savings Plan at Deere?

Yes, employees may have the option to take loans against their 401(k) Savings Plan at Deere, subject to the plan's rules and limits.

What investment options are available in Deere's 401(k) Savings Plan?

Deere's 401(k) Savings Plan offers a variety of investment options, including mutual funds, target-date funds, and company stock.

How often can employees change their contribution amounts to Deere's 401(k) Savings Plan?

Employees can change their contribution amounts to Deere's 401(k) Savings Plan at any time, subject to plan rules and limits.

What happens to my 401(k) Savings Plan at Deere if I leave the company?

If you leave Deere, you can choose to roll over your 401(k) Savings Plan balance to another retirement account, cash out, or leave it in the plan, depending on the plan's rules.

Are there penalties for withdrawing funds from Deere's 401(k) Savings Plan before retirement?

Yes, there may be penalties for early withdrawals from Deere's 401(k) Savings Plan before age 59½, along with potential tax implications.

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

Deere provides RSUs and stock options to eligible employees.