New Update: Healthcare Costs Increasing by Over 60% in Some States. Will you be impacted?

Illinois Tool Works Employees: Strategic Ways to Reduce Capital Gains on Appreciated Stock

Healthcare Provider Update: Healthcare Provider for Illinois Tool Works: Illinois Tool Works (ITW) primarily partners with Blue Cross Blue Shield (BCBS) of Illinois as their healthcare provider. This choice reflects a focus on comprehensive coverage options for their employees, aligning with the company's commitment to employee health and well-being. Potential Healthcare Cost Increases in 2026: In 2026, healthcare costs are expected to surge, with Blue Cross Blue Shield in Illinois anticipating an overall premium increase of approximately 27%. This spike is driven by a confluence of factors, including escalating medical expenses, diminishing federal premium subsidy support, and substantial hikes from major insurers. As the Affordable Care Act premiums rise sharply-potentially impacting 22 million enrollees-ITW's employees may face considerable out-of-pocket costs if no congressional action is taken to extend the enhanced subsidies. This underscores the necessity for proactive strategies in managing healthcare expenses amidst rapidly changing market dynamics. Click here to learn more

'Illinois Tool Works employees can benefit from understanding that strategies like a Section 351 exchange, charitable donations, and tax loss harvesting may work together to help manage appreciated stock efficiently while aligning with broader long-term financial goals.' – Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.

'Illinois Tool Works employees should recognize that thoughtful planning with tools such as Section 351 exchanges, gifting strategies, and tax loss harvesting can help them manage highly appreciated stock while supporting both personal and philanthropic objectives.' – Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

How a Section 351 exchange can defer capital gains on highly appreciated stock.
Alternative tax-efficient strategies such as charitable donations, tax loss harvesting, and gifting.
The role of inheritance rules, step-up in basis, and combined approaches in long-term tax planning.

A Tax-Aware Q&A on How to Manage Highly Appreciated Stock

From the Section 351 exchange to other practical approaches, this Q&A addresses key considerations Illinois Tool Works employees may encounter when dealing with highly appreciated shares.

Section 351 Exchange: The Fundamental Approach

Q: What is an exchange under Section 351?
A: Under certain circumstances, an investor may transfer property, such as highly appreciated shares, to a company in exchange for its stock under a provision of the Internal Revenue Code that allows the deferral of capital gains or losses.

Q: What is the primary advantage of exchanging my appreciated stock through a Section 351 exchange?
A: The main advantage is tax deferral. Gains transferred to corporations may be postponed under Section 351, though this applies only if specific diversification requirements are met, especially when transferring to investment companies like exchange-traded funds (ETFs). ¹

Q: What is meant by the “Control Test”?
A: The investor or group of investors who use their portfolio assets to fund the new entity must own at least 80% of the voting power and 80% of the total number of shares of all other classes of stock in the new company immediately after the exchange. ¹

Q: When seeding an ETF, how is the Control Test usually satisfied?
A: It is typically satisfied by either a single substantial investor making a significant asset contribution or multiple investors pooling assets to create a seeding pool for the ETF’s launch.

Q: What is the ultimate tax payment date for the deferred gain?
A: The deferred gain is recognized when the ETF shares acquired through the exchange are sold; distributions from taxable funds must also be reported in the meantime.

Other Tax-Efficient Techniques

Q: What is a straightforward method, aside from a Section 351 exchange, to sell highly appreciated shares without incurring large taxes?
A: Donating shares directly to a qualified charity is one option that some Illinois Tool Works employees may benefit from.

Q: What tax advantages come with donating valuable stock to a charity?
A: Subject to holding period and adjusted gross income (AGI) limits, you can bypass capital gains taxes on the appreciation and may receive an income tax deduction for the stock’s full fair market value.

Q: What is a Donor-Advised Fund (DAF)?
A: A DAF allows you to donate appreciated stock, receive an immediate tax deduction, and then recommend grants to charities over time, while the assets in the DAF grow without tax impact. ²

Q: Can I give a family member my appreciated stock as a gift?
A: Yes. In most cases, the cost basis from the donor carries over to the recipient.

Q: Why would I give a family member in a lower tax bracket appreciated stock?
A: If they sell the stock, the lower income could result in a reduced capital gains rate, potentially as low as 0% for long-term gains. ³

Tax Loss Harvesting and Other Approaches

Q: What is harvesting tax losses?
A: Selling investments at a loss to offset gains from other sales is known as tax loss harvesting, a strategy sometimes considered by Illinois Tool Works employees seeking opportunities to leverage bouts of market volatility.

Q: Can I deduct a certain amount of loss from my regular income?
A: Yes. If your capital losses exceed your gains, you can use up to $3,000 per year ($1,500 if married filing separately) to offset ordinary income, with remaining losses carried forward indefinitely. ⁴

Q: What is a Qualified Opportunity Fund (QOF)?
A: A QOF provides investors with tax incentives for investing in tracts of land designated as 'opportunity zones'. Capital gains reinvested in a QOF within 180 days of being realized can be temporarily tax deferred, while QOF investments helpd for at least 10 years may confer a permanent capital gains exclusion. ⁵ That said, 2025 legislation changes may prompt IRS updates to this rule.

Inheritance and Step-Up in Basis

Q: What is meant by a “step-up in basis”?
A: This adjusts an inherited asset’s cost basis to its fair market value at the time of the owner’s death, eliminating capital gains accumulated during their lifetime. ⁶

Q: If I gift shares while living, will I receive a step-up in basis?
A: No. The original cost basis transfers to the recipient without adjustment.

Determining the Right Strategy

Q: What is the best course of action for me?
A: The most suitable approach will depend on factors such as your gain size, income level, charitable intentions, and liquidity needs.

Q: Do any of these strategies call for professional guidance?
A: Yes. Given the complexity of the tax code, working with a qualified financial advisor and tax professional is strongly recommended before implementing these strategies.

Q: Is it possible to combine these strategies?
A: Yes. For example, you might execute a Section 351 exchange on part of your portfolio for tax-deferred rebalancing while donating another portion to a DAF for an immediate deduction.

Q: Is there a loophole in the Section 351 exchange?
A: No. This is a legitimate tax code provision designed for corporate restructuring and adapted for use in the ETF market. It is intended for tax deferral, not permanent tax elimination.

Featured Video

Articles you may find interesting:

Sources:

1. Kitces. ' Using Section 351 Exchanges to Tax-Efficiently Reallocate Portfolios With Embedded Gains ,' by Ben Henry-Moreland and Brent Sullivan. 12 Mar. 2025.

2. Kiplinger. “ A Donor-Advised Fund Can Give Your Charitable Giving a Boost ,” by Samuel Gaeta. 9 May 2024.

3. Internal Revenue Service. “ Topic No. 409, Capital Gains and Losses .” IRS.gov , 8 July 2025.

4. Wealth Enhancement. ' 6 Essential Tax-Loss Harvesting Tips ,' by Jim Wiley. 6 April 2022.

5. Congressional Research Service. ' Tax Incentives for Opportunity Zones ,' by Donald Marples. 26 Apr. 2022.

6. Investopedia. “ Carryover Basis: What It Is, How It Works, Gift Taxes ,” by Julia Kagan. 16 Jan. 2023.

What retirement savings options does Illinois Tool Works offer to its employees?

Illinois Tool Works offers a 401(k) plan as part of its retirement savings options for employees.

How can employees of Illinois Tool Works enroll in the 401(k) plan?

Employees of Illinois Tool Works can enroll in the 401(k) plan by completing the enrollment process through the company’s benefits portal or by contacting the HR department for assistance.

Does Illinois Tool Works provide a company match for the 401(k) contributions?

Yes, Illinois Tool Works provides a company match for employee contributions to the 401(k) plan, subject to specific terms and conditions.

What is the maximum contribution limit for the 401(k) plan at Illinois Tool Works?

The maximum contribution limit for the 401(k) plan at Illinois Tool Works is determined by the IRS guidelines, which can change annually.

Can employees of Illinois Tool Works take loans against their 401(k) savings?

Yes, employees of Illinois Tool Works may have the option to take loans against their 401(k) savings, subject to the plan's rules.

What investment options are available in the Illinois Tool Works 401(k) plan?

The Illinois Tool Works 401(k) plan offers a variety of investment options, including mutual funds, target-date funds, and other investment vehicles.

How often can employees change their contribution amount to the Illinois Tool Works 401(k) plan?

Employees of Illinois Tool Works can typically change their contribution amount on a quarterly basis or as specified in the plan details.

What happens to my Illinois Tool Works 401(k) if I leave the company?

If you leave Illinois Tool Works, you can choose to roll over your 401(k) balance to another retirement account, keep it in the Illinois Tool Works plan (if eligible), or withdraw the funds, subject to taxes and penalties.

Is there a vesting schedule for the company match in the Illinois Tool Works 401(k) plan?

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

Can part-time employees participate in the Illinois Tool Works 401(k) plan?

Yes, part-time employees at Illinois Tool Works may be eligible to participate in the 401(k) plan, depending on specific criteria set by the company.

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

Name of Pension Plan: Illinois Tool Works Pension Plan Years of Service and Age Qualification: Employees typically need to have a minimum of 5 years of service to qualify for the pension plan. Full benefits may be available to employees who are at least 65 years old or have reached a combination of age and service requirements totaling at least 85 years. Pension Formula: The pension is calculated based on years of service and the average of the highest-paid years of salary. For example, it may be calculated as 1.5% of the average of the highest 5 years of salary multiplied by years of service. Name of 401(k) Plan: Illinois Tool Works 401(k) Plan Who Qualifies: All full-time employees who are at least 21 years old and have completed 90 days of service are eligible to participate in the 401(k) plan. 401(k) Plan Features: Employees can contribute a percentage of their salary up to the annual limit set by the IRS. The company may provide matching contributions up to a certain percentage of the employee's contributions. Document: Illinois Tool Works 2024 Benefits Summary

Restructuring and Layoffs: In 2023, Illinois Tool Works announced a restructuring plan aimed at streamlining operations and improving efficiency. This plan included workforce reductions in certain sectors to adapt to shifting market demands and economic pressures. The company stated that these changes are intended to bolster its competitive position in a challenging economic environment. The importance of addressing this news is heightened due to the current economic landscape, where companies are adjusting their structures to maintain profitability amid fluctuating economic conditions. Understanding these changes is crucial for employees and stakeholders to navigate the evolving business environment and its impact on their roles and benefits.

ITW offers stock options and RSUs as part of their employee compensation packages. Stock options at ITW allow employees to purchase company stock at a set price, usually granted to senior executives and key employees. ITW provides RSUs, which are granted to employees as a form of equity compensation, usually vesting over several years. The company typically awards these to employees based on performance and seniority.

Health Insurance: ITW offers comprehensive health insurance plans, including medical, dental, and vision coverage. Employees can choose from multiple plan options to fit their needs. Wellness Programs: The company provides wellness programs that include resources for mental health, fitness, and preventive care. Retirement Savings: ITW offers 401(k) plans with company matching contributions and other financial wellness programs.