Samuel Zell, the Chicago Tribune, and the Emergence of the S ESOP: Understanding the Tax Advantages and Disadvantages of S ESOPs

Samuel Zell’s acquisition of the Chicago Tribune Company (the Tribune) in December 2007 using a little-known type of Employee Stock Ownership Plan (ESOP) made headlines. In a complicated transaction, which took nearly a year to complete, the Tribune converted from a subchapter C corporation to a subchapter S corporation, established an ESOP that purchased 100 percent of the company’s equity, and sold Zell a call option giving him the right to purchase 40 percent of the company’s equity. Press reports claim that Zell’s novel structure enabled Zell to outbid other suitors. And financial commentators predict that many acquirers will employ that same structure as soon as acquisition activity picks up. Zell’s Tribune transaction also caught the eye of legislators, including Congressman Charles Rangel, who introduced a bill that would increase the tax on indirect claims – such as the one owned by Zell – on the equity of an S corporation held by an ESOP (synthetic equity). Although ESOPs are more than 30 years old, until 1998, an S corporation could not sponsor an ESOP. Over the last ten years, so-called S ESOPs have grown rapidly, but largely outside of public view. The Tribune transaction has focused a bright light on S ESOPs and there are some who believe that their current tax treatment is too favorable. Yet, there has been little in-depth analysis of the tax treatment of S ESOPs. Accordingly, this paper attempts to fill that gap by presenting a systematic economic evaluation of the tax consequences of using an S ESOP. It seeks to describe both qualitatively and quantitatively the tax advantages and disadvantages of using an S ESOP (with or without synthetic equity) relative to alternative available structures. This paper also estimates by how much the S ESOP structure likely allowed Zell to increase his bid for the Tribune

Section 83(b) Election for Restricted Stock: A Joint Tax Perspective

In the wake of the Financial Accounting Standard Board\u27s decision to require firms that grant employee stock options (ESOs) to treat such options as an expense, many large and sophisticated firms are switching from ESOs to restricted stock. Restricted stock - stock granted to an employee as part of her compensation and subject to the condition that if she leaves the firm within a period of time (often 3 years) she forfeits the stock - appears to be on its way to becoming the dominant form of equity-based pay in the United States. Yet, in spite of its prominence, little attention has been paid to how employers should design their restricted stock programs in light of tax considerations. The tax consequences to both the employee and the employer of a grant of restricted stock are deferred until the restriction lapses and the stock vests. There is however an exception to that general rule: If, within 30 days of receiving the stock, the employee makes what is called the Section 83(b) election, then both the employer and the employee are taxed at the time of grant. Employing a joint tax perspective that looks at the tax consequences to both the employer and the employee, this paper attempts to answer several compensation design issues raised by the use of restricted stock. Specifically, I address the question under what circumstances should the employer charge the employee explicitly for her restricted shares and when should the employer charge implicitly for the restricted stock through a lower salary. I also look at the desirability to the employee, the employer, and the employee and employer together of the employee making the Section 83(b) election. Finally, I look at the value to the employee and cost to the employer of the employee\u27s option to wait 30 days until making the Section 83(b) election

Reconsidering International Tax Neutrality

For decades, U.S. international tax policy has shifted back and forth between territorial-source-exemption taxation and worldwide-residence-credit taxation. The former is generally associated with capital import neutrality (CIN) and the latter with capital export neutrality (CEN). One reason why national tax policy has shifted back and forth between those benchmarks is because it is widely accepted that a tax system cannot simultaneously satisfy both CEN and CIN unless tax rates on capital are harmonized across jurisdictions. In this essay, I argue that the international tax literature contains two different and conflicting definitions for CIN. Under one definition, which goes back at least to Peggy Musgrave’s early writings and which has been adopted by politicians, lawyers and lay readers, CIN is understood to refer to a tax system that was competitively neutral. That idea can be conceptualized as a tax system that does not distort the ownership of capital (ownership neutrality). In the economics literature, ownership neutrality is closely associated with the recent work of Mihir Desai and James Hines, who coined the phrase capital ownership neutrality (CON) to describe a tax system that does not distort the ownership of assets. Under the other definition, which goes back to Thomas Horst and which has been broadly adopted by professional economists, CIN is understood to refer to a tax system that does not distort the consumption – savings choice (savings neutrality). In this essay, I show that the widely accepted and often repeated proof that a tax system cannot simultaneously satisfy both CEN and CIN is based on the assumption that CIN refers to saving neutrality. In contrast, when CIN is interpreted as ownership neutrality, the global adoption of a worldwide tax system simultaneously satisfies both CEN and CIN. However, global adoption of a territorial tax system still cannot simultaneously achieve both CEN and CIN because a territorial tax system violates CEN. Not surprisingly, the use of the term CIN to denote two different types of neutrality – ownership neutrality and savings neutrality – has produced much confusion for those trying to understand, influence and set international tax policy. Accordingly, I recommend that commentators either stop talking about CEN and CIN and talk instead about locational, ownership, and savings neutrality or if they continue to talk about CIN that they clearly specify whether they mean CIN as ownership neutrality or as saving neutrality

The Tax Cuts and Jobs Act’s Incorporation “Incentive”

Many observers have asserted that the reduced corporate tax rate instituted by the 2017 Tax Cuts and Jobs Act (TCJA) has transformed entity choice for business owners, incentivizing owners of businesses structured as sole proprietorships or passthrough entities to incorporate their businesses and to use these new corporations as pocketbook investment vehicles to invest in and hold portfolio investments, substantially reducing wealthy individuals’ tax obligations and Treasury’s tax collections. This brief offers a different view, and discusses why predictions of widespread conversions to the corporate form at a substantial cost to the fiscal position of the U.S. are overstated. The brief explores the various purported tax advantages to incorporating, both when business owners are looking to invest substantial profits in portfolio assets, as well as when retained earnings are reinvested in the business and produce ordinary income.https://repository.upenn.edu/pennwhartonppi/1069/thumbnail.jp

Gray-Market Imports: Causes, Consequences and Responses

This article explores the issue of gray-market imports. The author explains the four causes of gray-market imports and explores the possibility of private remedies in order to stem the flow of these imports. The article then turns to the possibility of protection in the public sector by discussing pertinent statutory provisions and the development of the case law in this area

On the Disparate Treatment of Business and Personal SALT Payments

The Tax Cuts and Jobs Act, H.R. 1, would eliminate the federal income tax deduction for nonbusiness state and local taxes while maintaining the deduction for business state and local taxes. That disparate treatment has generated a storm of negative commentary. In this short essay, I consider whether the federal tax law should allow a deduction for business state and local taxes assuming that there is no deduction for nonbusiness state and local taxes. I argue that investors and businesses, including pass-through businesses, should be allowed to deduct state and local property and sales taxes, but not general income taxes

Compaq Redux: Implicit Taxes and the Question of Pre-tax Profit

This paper takes a new look at the cross-border dividend-stripping transactions that gave rise to the Fifth Circuit’s opinion in Compaq v. Commissioner and the Eighth Circuit’s opinion in IES Industries v. Commissioner. In both cases, the circuit courts held for the taxpayers and rejected the Commissioner’s claim that the transactions lacked economic substance because the taxpayers were sure to lose money on the transactions before taxes. These cases generated extensive commentary that was split into two diametrically opposed camps. One group argued that the decisions were correct because the transactions were economically profitable business transactions. The other group argued that the transactions were blatant, abusive tax shelters; and that the courts should have struck them down. Because the commentators in the second group conceded that the transactions generated a pre-tax profit, these commentators also offered a range of proposals to modify or replace the pre-tax profit test. Although the tax benefit of crossborder dividend-stripping was sharply reduced by subsequent Congressional enactments, that action hid rather than resolved the issue whether the tax shelter jurisprudence is fundamentally flawed because there is a class of abusive transactions that produce a guaranteed profit before tax, but do not run afoul of the anti-abuse provisions in the tax law. This paper argues that the Compaq and IES Industries transactions do not reveal any fundamental failings with either anti-abuse jurisprudence generally or the pre-tax profit test in particular. This paper demonstrates that the circuit courts reached the wrong conclusions in those cases because the parties, the courts, and the commentators all ignored implicit taxes. That is not surprising because the implicit taxes in these cases were difficult to see. These taxes were negative implicit taxes, which drove down the cum dividend price of the stripped stock, and therefore made the transactions appear profitable before taxes. However, once implicit taxes are taken into account, the transactions in those cases are properly understood to be unprofitable before taxes. Finally, nearly ten years ago, Charlotte Crane observed that tax doctrine has all but ignored implicit taxes and she challenged commentators, lawyers and judges to think carefully about how implicit taxes can be incorporated into tax doctrine. My proposal to calculate pre-tax profit for the purpose of anti-abuse jurisprudence before both implicit and explicit taxes is, I believe, the first proposal to explicitly recognize implicit taxes in tax doctrine