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Gray Television Employees: Strategic Ways to Reduce Capital Gains on Appreciated Stock

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'Gray Television 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.

'Gray Television 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 Gray Television 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 Gray Television 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 Gray Television 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 type of retirement plan does Gray Television offer to its employees?

Gray Television offers a 401(k) savings plan to help employees save for retirement.

Does Gray Television match employee contributions to the 401(k) plan?

Yes, Gray Television provides a matching contribution to the 401(k) plan, which enhances employees' retirement savings.

How can employees at Gray Television enroll in the 401(k) plan?

Employees can enroll in the 401(k) plan through the company's HR portal or by contacting the HR department for assistance.

What is the eligibility requirement for Gray Television employees to participate in the 401(k) plan?

Most employees at Gray Television are eligible to participate in the 401(k) plan after completing a specified period of employment, typically 30 days.

Can Gray Television employees choose how their 401(k) contributions are invested?

Yes, employees at Gray Television can choose from a variety of investment options for their 401(k) contributions.

What is the maximum contribution limit for Gray Television employees participating in the 401(k) plan?

The maximum contribution limit for Gray Television employees is subject to IRS regulations, which may change annually.

Does Gray Television offer any financial education resources for employees regarding the 401(k) plan?

Yes, Gray Television provides financial education resources and tools to help employees make informed decisions about their 401(k) savings.

Are there any fees associated with managing the 401(k) plan at Gray Television?

Yes, like most 401(k) plans, there may be administrative fees associated with managing the plan at Gray Television.

Can Gray Television employees take loans against their 401(k) savings?

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

What happens to a Gray Television employee's 401(k) savings if they leave the company?

If a Gray Television employee leaves the company, they can roll over their 401(k) savings into another retirement account or take a distribution, depending on their preference.

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

Gray Television Pension Plan Name of the Plan: Gray Television does not appear to have a traditional defined benefit pension plan as of the latest available reports. Eligibility: Gray Television primarily offers a 401(k) plan rather than a traditional pension plan. Pension Formula: Not applicable.. Gray Television 401(k) Plan Name of the Plan: Gray Television 401(k) Plan. Eligibility: Employees are eligible to participate in the 401(k) plan after completing 90 days of service. 401(k) Plan Details: The plan includes employer matching contributions up to a certain percentage.

Restructuring and Layoffs: In August 2023, Gray Television announced a restructuring plan to streamline operations and improve efficiency. This included the elimination of certain positions, particularly in non-core areas. The company cited the need to adapt to changing media consumption patterns and economic pressures as key reasons for these changes. The restructuring is part of a broader strategy to enhance profitability and maintain competitive advantage in the evolving media landscape. It is crucial to address this news due to the current economic environment, which may impact job stability and career planning in the media sector. Changes to Company Benefits and Retirement Plans: In July 2024, Gray Television updated its employee benefits package, which included modifications to its pension and 401(k) plans. The company introduced changes aimed at aligning retirement benefits with industry standards and addressing financial sustainability. These adjustments are part of a broader effort to manage costs and ensure long-term financial health amidst fluctuating market conditions. Employees should stay informed about these changes due to the implications they may have on retirement planning and financial security in the context of ongoing economic uncertainty.

Gray Television (GT) Stock Options and RSUs (2022) Stock Options: Gray Television (GT) offered stock options to select executives and senior management in 2022. The options were granted as part of the company’s long-term incentive plan to attract and retain top talent. Restricted Stock Units (RSU): RSUs were granted to executives as well as key employees based on performance and tenure. These units were designed to align the interests of employees with shareholders. Gray Television (GT) Stock Options and RSUs (2023) Stock Options: In 2023, Gray Television (GT) continued to provide stock options primarily to senior executives and high-performing employees. These options were part of a revised incentive compensation plan. Restricted Stock Units (RSU): RSUs were granted to a broader range of employees, including mid-level management, with vesting schedules tied to performance metrics. Gray Television (GT) Stock Options and RSUs (2024) Stock Options: The company issued new stock options in 2024 under a refreshed equity incentive program. These options were available mainly to upper management and key contributors. Restricted Stock Units (RSU): RSUs in 2024 were expanded to include more employees, aiming to foster long-term commitment and reward performance over time.

Health Benefits Information (2022-2024) 1. Gray Television Official Website: Website: Gray Television Careers Details: Gray Television offers a variety of health benefits including medical, dental, and vision insurance. Their benefits package typically includes options for both employee and family coverage, with various plan tiers available to cater to different needs. 2. Health Insurance Plans: Types of Plans: Gray Television provides several health insurance plans which may include Health Maintenance Organization (HMO), Preferred Provider Organization (PPO), and High Deductible Health Plans (HDHPs). Specific details about plan costs and coverage options are generally available to employees upon hiring and during open enrollment periods. 3. Employee Benefits Review Websites: Glassdoor: Employee reviews often mention health benefits in the context of overall compensation. The benefits are generally considered competitive, with particular emphasis on the quality of medical coverage. Indeed: Similar to Glassdoor, reviews on Indeed highlight that health benefits are a key part of Gray Television’s compensation package. There might be variations in the benefits offered based on job position and location. Payscale: Offers insights into average salaries and benefits, noting that Gray Television provides standard health insurance options. LinkedIn: Discussions on LinkedIn sometimes include employee testimonials about the company’s benefits, including healthcare. These reviews typically praise the availability of comprehensive health plans. Comparably: Provides information on employee satisfaction with health benefits. Gray Television’s benefits are generally rated well compared to industry standards. 4. Recent Healthcare News: Healthcare Initiatives: Recent updates or changes to health benefits are often tied to broader company policy changes or industry trends. Specific details about recent changes might be less frequently updated in public sources but can be available through employee reviews or official company announcements. Employee Health Programs: Gray Television may offer wellness programs or health initiatives, such as mental health support or wellness challenges, though specific details might not always be prominently featured. Healthcare-Related Terms and Acronyms HMO (Health Maintenance Organization): A type of health insurance plan that requires members to get care from a network of doctors and hospitals. PPO (Preferred Provider Organization): A plan that offers more flexibility in choosing healthcare providers and does not require referrals for specialists. HDHP (High Deductible Health Plan): A plan with lower premiums and higher deductibles, often paired with Health Savings Accounts (HSAs). HSA (Health Savings Account): A tax-advantaged account that can be used to pay for qualified medical expenses, often associated with HDHPs.