Tax Blog

Tribune Media vs. IRS: Implications for Chicago’s Tax Landscape

By Kelly Hanley, Esq., Chicago Tax Attorney

In the opinion of this Chicago Tax Attorney, few cases capture the intricate dynamics of debt, equity, and the IRS’s stance as vividly as the ongoing legal battle involving Tribune Media Co. and the IRS. Central to this dispute is the sale of the Chicago Cubs, a transaction that not only enthralled baseball fans but also tax attorneys and legal experts in Chicago and beyond. This article delves into the complexities of this case, shedding light on critical tax considerations and legal principles at play.

Background: The Chicago Cubs Sale

In 2009, Tribune Media Co. orchestrated a deal to transfer its controlling interest in the Chicago Cubs franchise, along with related assets, to the Ricketts family through Chicago Baseball Holdings LLC (CBH). This high-profile transaction in Chicago’s sports and business circles involved not just the transfer of a beloved baseball team but also a nuanced financial arrangement that would soon attract the IRS’s audit scrutiny.

The Core of the Dispute: Debt vs. Equity

At the heart of the conflict lies a critical question: Should certain components of the funding for this transaction be treated as debt or equity? This distinction holds significant tax implications, making it a focal point of contention between Tribune and the IRS.

The Transaction Structure

The deal’s structure was complex. Chicago Baseball Holdings, in a strategic move, made a substantial distribution to Tribune Media Co. The amount was staggering: $714 million in total. This distribution was not straightforward cash but was composed of two distinct types of debt instruments.

The first tranche of this funding was a $425 million senior debt sourced from third-party lenders. This form of debt is typically considered safer from an investment standpoint, as it is prioritized in terms of repayment over other types of debt in the event of a default. The involvement of external lenders in this part of the transaction added a layer of complexity and legitimacy to the financial structure.

The second and more contentious part of the distribution was the $249 million in subordinated debt. This debt came from RAC Education Trust Finance LLC, a significant part of which was owned by Marlene Ricketts. Subordinated debt is generally considered riskier than senior debt because it is lower in the hierarchy for repayment in case of insolvency. The involvement of RAC Education Trust Finance LLC, a closely related party, introduced additional layers of complexity and scrutiny.

Tribune Media Co.’s position on this financial arrangement was clear. They argued that both the senior and subordinated debt components of the distribution should be treated as nontaxable under specific tax regulations. This stance was rooted in a strategic interpretation of the tax code, aimed at maximizing the financial efficiency of the transaction.

However, the IRS viewed the matter differently, particularly concerning the $249 million subordinated debt. The tax authority’s disagreement stemmed from a fundamental question in tax law: when does a financial instrument cease to be a debt and instead be treated as equity? The IRS scrutinized the nature of the subordinated debt, raising questions about its true character and the intent behind its use in this transaction.

In the government’s view, the close relationship between the lending and borrowing entities, combined with the terms and conditions of the subordinated debt, pointed towards an equity-like nature rather than that of a genuine debt. This interpretation by the IRS challenged Tribune’s tax strategy, setting the stage for a legal dispute that would delve into the intricate nuances of debt, equity, and their tax implications.

Tax Court’s Split Decision

The Tax Court’s ruling in October 2021 was a mixed bag. On one hand, the court found itself in agreement with Tribune regarding the $425 million in senior debt. This portion, borrowed from third-party lenders, was considered by the court to be genuine debt, thereby making it allocable to Tribune. This part of the ruling was a win for Tribune, aligning with their stance and affirming their tax treatment of the senior debt.

However, the court’s view sharply diverged when it came to the $249 million in subordinated debt provided by RAC Education Trust Finance LLC. Here, the court took a turn that Tribune did not anticipate. Instead of recognizing this amount as a genuine debt, the Tax Court reclassified it as equity. This reclassification was pivotal – it meant that this portion of the transaction would be considered taxable, diverging significantly from Tribune’s tax strategy and interpretation of the law.

The Tax Court’s split decision did not settle the matter; rather, it set the stage for further legal scrutiny. Both Tribune and the IRS found aspects of the decision unpalatable and thus chose to appeal. This move signaled the beginning of an even more detailed and nuanced examination of the legal and tax principles at the heart of this case.

Tribune’s Arguments

Tribune’s legal strategy hinges on emphasizing the intent of the parties involved in the transaction. They argue this intent should be the determining factor in assessing the nature of the $249 million subordinated loan. Tribune posits that both parties to the transaction, themselves and the Ricketts family through RAC Education Trust Finance LLC, clearly intended this sum to be a loan, not an equity investment.

This emphasis on intent is crucial. Tribune believes that if the court were to delve into the motivations and understandings of the parties at the time of the transaction, it would have found clear evidence supporting the classification of the amount as debt. This approach seeks to move beyond a rigid, formulaic analysis and delve into the practical realities and mutual understandings that underpinned the transaction.

Tribune is critical of the Tax Court’s approach, which they view as overly mechanical and not reflective of the transaction’s real-world complexities. The Tax Court applied a 13-factor test from the case Dixie Dairies Corp. v. Commissioner. While this test is a standard tool in tax law for distinguishing between debt and equity, Tribune contends its application in their case was too formulaic and failed to capture the nuances of their specific situation.

They argue the Tax Court’s reliance on this test led to an oversimplified analysis, one that did not adequately take into account the full spectrum of facts and intentions that characterized the transaction. Tribune believes a more nuanced interpretation is necessary, one that considers what the 13 factors collectively reveal about the nature of the subordinated loan.

Tribune’s appeal to the court is, in essence, a call for a more holistic understanding of the transaction. They want the court to look beyond the checkboxes of the 13-factor test and consider the broader context: the negotiations, the agreements made, and the practicalities of how the transaction was structured and understood by those involved.

This approach is not just about reclassifying the subordinated loan; it is about advocating for a more flexible, context-aware application of tax law. Tribune’s arguments underscore a tension often present in tax law: the need for clear, consistent rules versus the reality that financial transactions can be highly complex and unique, defying simplistic categorization.

The Justice Department’s Counterarguments

A key element of the Justice Department’s argument centers on the nature of the negotiations that led to the structuring of the $249 million in subordinated debt. They point out that these negotiations did not occur at arm’s length, a term used in both legal and financial contexts to describe agreements made by parties independently and on equal footing.

In typical arm’s-length transactions, each party acts in their own interest and is not subject to the other’s control or influence. The Justice Department argues that this was not the case with the subordinated debt in the Tribune transaction. They highlight the fact that the lending and borrowing entities were closely related and controlled by the Ricketts family, suggesting that the terms of the debt might not have been negotiated as rigorously or objectively as they would have been between unrelated parties.

Another cornerstone of the government’s argument is the intra-family dynamics involved in the transaction. The subordinated debt was financed by an entity significantly owned by Marlene Ricketts, a member of the family that was acquiring the Chicago Cubs. The Justice Department argues that this family relationship between the borrower and the lender blurred the lines between what would typically be considered a debtor-creditor relationship and what might instead resemble an equity investment within a family-owned business structure.

The government contends such intra-family dealings often lack the clear-cut boundaries and formalities that characterize typical commercial lending transactions. They suggest that in such contexts, the movement of money might be more akin to equity investment, where funds are put into a business with an expectation of a return, rather than a loan with an obligation for repayment under specific terms.

Based on these observations, the Justice Department supports the Tax Court’s ruling that classified the $249 million as equity. In their view, the nature of the negotiations and the familial ties involved pointed away from a traditional loan structure. They argue these factors, taken together, indicate the subordinated debt was, in substance, more similar to an equity investment, where the lender (in this case, the Ricketts-controlled entity) had an ongoing financial interest in the success of the business (CBH and, by extension, the Chicago Cubs) rather than a mere interest in being repaid a borrowed sum.

This case is a classic example of the legal intricacies involved in distinguishing debt from equity in tax matters. It highlights several key considerations:

  • The Importance of Arm’s-Length Negotiation: The absence of such negotiation, as the government points out, often tilts the balance toward equity classification.
  • The Role of Family Dynamics: In cases involving family-owned entities, the scrutiny is higher, with a presumption that transactions might not always reflect commercial realities.
  • The Weight of Intent vs. Formality: While Tribune emphasizes intent, the IRS and the courts often look for formal indicia consistent with debt, such as documented agreements and adherence to repayment schedules.

Supreme Court and Seventh Circuit Views

A significant aspect of Tribune’s argument rests on precedents set by the Supreme Court and the Seventh Circuit Court of Appeals. These courts have historically underscored the importance of recognizing the separateness of legal entities in tax considerations, especially when each entity serves a distinct business purpose.

The doctrine of separate legal entities is a fundamental concept in both corporate law and tax law. It posits that different legal entities, such as corporations or limited liability companies, should be treated as separate from their owners for legal and tax purposes. This separation implies that the debts, obligations, and liabilities of a business entity are distinct from those of its shareholders or related entities.

The Supreme Court and the Seventh Circuit have consistently upheld this principle, recognizing that each legal entity, when properly formed and operated, should be viewed independently in the eyes of the law. This view is essential in ensuring that entities are taxed based on their own activities and financial transactions, rather than being indiscriminately merged with their related entities or owners for tax purposes.

In the case at hand, Tribune Media Co. leans heavily on these judicial precedents to bolster its argument. Tribune points out that Chicago Baseball Holdings LLC and RAC Education Trust Finance LLC were distinct legal entities, each with its own separate legal identity, ownership structure, and business purpose.

Chicago Baseball Holdings was established primarily to own and operate the Chicago Cubs, representing a significant investment in the sports and entertainment industry. On the other hand, RAC Finance was structured as an investment vehicle, primarily managing the private funds of Marlene Ricketts. Tribune argues that this clear delineation in purpose and structure between the two entities supports its stance that the financial transactions between them should be respected as legitimate and in line with the principle of separate legal entities.

Tribune’s reliance on this legal principle is strategic. By highlighting the distinct roles and purposes of Chicago Baseball Holdings and RAC Finance, Tribune aims to demonstrate that the subordinated debt transaction was a bona fide business arrangement between two separate entities. This argument is integral to countering the IRS’s and the Tax Court’s view that the subordinated debt was akin to an equity investment, primarily due to the close familial ties and the lack of arm’s-length negotiation.

Tribune’s goal is to persuade the court that, in line with the precedents set by the Supreme Court and the Seventh Circuit, the transaction should be viewed through the lens of the entities’ separateness and independent business objectives, rather than being overshadowed by the relationships of the individuals behind these entities.

The Role of Fiduciary Duty

An intriguing aspect of this case is the focus on Thomas Ricketts’ fiduciary duty in managing both the lending and borrowing entities. Fiduciary duty in a corporate context refers to the obligation of an individual, often a director, officer, or manager, to act in the best interest of the company and its stakeholders. This duty encompasses both a duty of care – to act with the diligence and prudence reasonably expected – and a duty of loyalty – to prioritize the interests of the company and its shareholders over personal interests. In the case of Thomas Ricketts, this fiduciary duty extended to both entities involved in the transaction, each with its own set of stakeholders and interests.

Tribune’s argument hinges on the assertion that Thomas Ricketts’ fiduciary duty to both entities inherently compelled him to enforce the debt agreement. Tribune posits that despite the familial connections involved, Ricketts was legally bound to act in the best interest of both entities. This meant ensuring that the subordinated loan was treated as a genuine debt obligation, subject to enforcement and repayment, just like any other business loan.

This perspective aims to counter the government’s suggestion that familial ties and the lack of arm’s-length negotiation in the transaction would inherently lead to the subordinated debt being treated more leniently, akin to equity. Tribune maintains that the presence of a fiduciary duty provided a safeguard against such leniency, ensuring that the financial obligations were upheld irrespective of family relationships.

The emphasis on fiduciary duty in this case raises broader questions about how such duties influence tax classification in family-controlled business transactions. Typically, the IRS and courts scrutinize transactions involving related parties to ensure that they reflect the economic realities and are not merely structured for tax advantages. The presence of a fiduciary duty adds a layer of complexity to this analysis.

In situations where an individual like Thomas Ricketts holds fiduciary responsibilities to related but legally distinct entities, the enforcement of financial agreements between these entities can be seen in a different light. Instead of being viewed solely through the lens of family relationships, the transactions can be analyzed in terms of the fiduciary obligations to uphold the entities’ separate interests. This perspective could influence how such transactions are classified for tax purposes, potentially differentiating them from straightforward family dealings where personal relationships might overshadow formal business agreements.

The Chicago Tax Landscape: Broader Implications

Chicago, with its vibrant business landscape, often becomes the backdrop for intricate tax disputes. This case exemplifies the type of complex transactions that can arise in major metropolitan areas, where large family-controlled businesses and high-profile deals are more common. For tax professionals in Chicago, cases like these are a rich source of learning and adaptation.

The outcome of this case will have significant implications for how businesses in Chicago structure their transactions, especially those involving related parties. It serves as a cautionary tale for companies to meticulously document their financial arrangements and ensure they align with both the form and substance required by tax law.

As the case progresses, it will likely influence how businesses in Chicago and beyond approach similar transactions. The final ruling could set a precedent affecting not just sports franchises but any business dealing with similar issues of debt, equity, and tax implications.

Implications for Tax Planning and Compliance

The ongoing legal battle between Tribune Media and the IRS offers several lessons for businesses and tax practitioners:

  • Thorough Documentation: The importance of meticulously documenting transactions cannot be overstated, especially in related-party dealings.
  • Understanding IRS Scrutiny: Transactions involving large sums, especially in family-controlled businesses, are likely to attract IRS audits. Understanding the criteria the IRS uses to evaluate such transactions is crucial.
  • Strategic Planning: This case underscores the need for strategic tax planning that considers both legal and practical aspects of a transaction.

Chicago Tax Attorney Insights

The Tribune Media Co. case against the IRS serves as a rich repository of insights for Chicago tax attorneys and tax resolution firms. It unravels a complex web of tax concepts, legal interpretations, and corporate transactions, offering a practical, real-world example of the challenges and intricacies of tax law.

Illuminating Complex Tax Concepts

For tax professionals, particularly in Chicago where the case has local significance, the Tribune Media dispute is a vivid illustration of the complexities inherent in tax law. It demonstrates how transactions can be viewed through different lenses – as debt or equity, as arm’s-length negotiations or familial agreements – and how these interpretations can significantly impact tax obligations. The case provides an opportunity for tax attorneys to dissect and explain these intricate concepts to their clients, enhancing their understanding of how tax law applies in complex financial scenarios.

The Value of Expert Advice

One of the key takeaways from the Tribune case is the indispensable value of expert advice in navigating the often murky waters of tax law. The nuances of the case – involving the distinction between debt and equity, the role of fiduciary duty, and the implications of intra-family transactions – underscore the need for skilled guidance. Tax attorneys and advisors are equipped to interpret and apply complex tax regulations to specific business scenarios, providing clarity and direction to their clients.

The Crucial Role of Tax Resolution Firms

Tax resolution firms play an instrumental role in advising businesses on how to structure their transactions to comply with tax laws while also meeting their financial goals. In cases like Tribune’s, where the structure of a transaction can significantly impact tax liabilities, the expertise of these firms becomes invaluable. They help businesses navigate the complex interplay between corporate finance and tax regulations, ensuring that transactions are not only financially sound but also legally compliant.

Beyond transaction structuring, these firms also provide critical guidance on maintaining compliance with evolving tax laws and regulations. They stay abreast of the latest tax developments, court cases, and IRS rulings, enabling them to offer up-to-date advice to their clients. This proactive approach to compliance is crucial in avoiding disputes with tax authorities and in minimizing the risk of costly litigation.

Perhaps most importantly, in the event of a dispute with the IRS, as was the case with Tribune Media, tax resolution firms represent businesses, advocating on their behalf. They bring to the table their expertise in tax law, negotiation skills, and experience in dealing with tax authorities. Their role involves not only defending their client’s position but also exploring avenues for resolution, whether through negotiation, settlement, or litigation.

For businesses in Chicago and beyond, the Tribune Media case serves as a reminder of the complexities of tax law and the value of having expert advisors by their side. Tax resolution firms and attorneys provide indispensable guidance, from structuring transactions and ensuring compliance to representing clients in disputes. Their expertise is not just a resource; it is a requirement in navigating the intricate and ever-changing landscape of tax law.


The Tribune Media vs. IRS case, set against the backdrop of Chicago’s dynamic business environment, offers a fascinating glimpse into the complexities of tax law. It highlights the challenges businesses face in structuring transactions and the importance of understanding the nuances of tax legislation. As this case unfolds, it will undoubtedly continue to be a topic of interest for Chicago tax attorneys and businesses alike.