Sean P. McNamee v. Department of the Treasury, Internal Revenue Service, Docket No. 05-6151-Cv

488 F.3d 100, 99 A.F.T.R.2d (RIA) 2871, 2007 U.S. App. LEXIS 12016
CourtCourt of Appeals for the Second Circuit
DecidedMay 23, 2007
Docket100
StatusPublished
Cited by52 cases

This text of 488 F.3d 100 (Sean P. McNamee v. Department of the Treasury, Internal Revenue Service, Docket No. 05-6151-Cv) is published on Counsel Stack Legal Research, covering Court of Appeals for the Second Circuit primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

Bluebook
Sean P. McNamee v. Department of the Treasury, Internal Revenue Service, Docket No. 05-6151-Cv, 488 F.3d 100, 99 A.F.T.R.2d (RIA) 2871, 2007 U.S. App. LEXIS 12016 (2d Cir. 2007).

Opinion

KEARSE, Circuit Judge.

Plaintiff pro se Sean P. McNamee, the single-member owner of a now-defunct limited liability company (or “LLC”) formed under Connecticut law, appeals from a judgment of the United States District Court for the District of Connecticut, Christopher F. Droney, Judge, rejecting his challenge to a determination by the Internal Revenue Service (“IRS”) under Treasury Regulations §§ 301.7701-2 and 301.7701-3, 26 C.F.R. §§ 301.7701-2 and 301.7701-3, that, because of his failure to exercise his option to have his LLC treated as a corporation, McNamee was person *103 ally liable for the LLC’s employment tax liabilities. McNamee alleged principally that the Treasury Regulations, and hence the IRS determination, were contrary (a) to state law treating an LLC and its members as separate entities, and (b) to provisions of the Internal Revenue Code (or “Code”). The district court, concluding that the Treasury Regulations were both consistent with the Code and reasonable, ruled in favor of the government. On appeal, McNamee pursues his contentions that the regulations are invalid because they contravene state law and the federal statutory scheme. For the reasons that follow, we affirm.

I. BACKGROUND

The material facts appear to be undisputed. McNamee was the sole proprietor of an unincorporated accounting firm, W.F. McNamee & Company LLC (“WFM-LLC”), a Connecticut limited liability company that ceased operation in March 2002. WFM-LLC employed an average of six persons.

The Internal Revenue Code imposes two forms of employment tax obligations on an employer (hereinafter “payroll taxes”). First, the employer is required to pay unemployment taxes, see 26 U.S.C. § 3301, and to make contributions to its employees’ social-security and Medicare benefits pursuant to the Federal Insurance Contributions Act (“FICA”), see id. § 3111. Second, the employer is required to withhold from employee compensation and remit to the government (a) employee income taxes, see id. § 3402, and (b) the employees’ own mandated FICA contributions, see id. §§ 3101, 3102(b). With respect to the third and fourth quarters of 2000 and all four quarters of 2001, WFM-LLC made no payment of any of the required payroll taxes.

The Code recognizes a variety of business entities — including corporations, companies, associations, partnerships, sole pro-prietorships, and groups — and, based on the classifications, treats the entities in various ways for income tax purposes. For example, the income of a corporate entity is generally subject to a double wave of taxation, in that the corporation is taxed directly, see 26 U.S.C. § 11(a), and its individual shareholders are further taxed on dividends paid to them out of the corporation’s income, see id. § 61(a)(7). In contrast, an unincorporated sole proprietorship that is treated as such is taxed only once: the owner simply lists his business income on Schedule C of his individual tax return; the proprietorship entity is not directly taxed, see generally id. § 61(a)(2); 26 C.F.R. § 301.7701-3(b).

As discussed in greater detail in Part II below, the Code’s definitions of various types of business entities are broad, and to some extent they overlap one another. See 26 U.S.C. § 7701(a). In an attempt to eliminate ambiguity, the Treasury Regulations instruct that certain entities must be classified as corporations, see 26 C.F.R. § 301.7701-2(b), while other entities are permitted to decide for themselves whether or not to be treated as corporations, see id. § 301.7701-3. Thus, an entity whose classification as a corporation is not required (referred to in the Regulations as an “eligible entity”), and which has only one owner, has the option of being classified either as an “association” — which is defined in § 301.7701-2(b)(2) as a corporation — or as a “sole proprietorship” that is to be “disregarded as an entity separate from its owner,” id. § 301.7701-2(a).

An eligible entity exercises that option simply by filing IRS Form 8832, entitled “Entity Classification Election,” having checked the appropriate box on the Form. See id. § 301.7701-3(c) (the “check-the- *104 box” regulation). In the absence of such an election, an eligible entity that has only one owner is disregarded as a separate entity. See id. § 301.7701-3(b).

WFM-LLC, McNamee’s LLC, was not required to be classified as a corporation, and McNamee elected not to have it treated as one. Thus, under the Treasury Regulations, WFM-LLC was disregarded as a separate entity and was treated as a sole proprietorship. WFM-LLC’s unpaid payroll taxes for 2000 and 2001 totaled $64,736.18. The IRS, having disregarded WFM-LLC as a separate entity, assessed those taxes against McNamee personally and placed a lien on his property.

McNamee filed a timely administrative appeal. He did not dispute WFM-LLC’s liability for the unpaid $64,736.18. However, pointing to sections of Connecticut law providing that members of an LLC are not personally liable for the debts of the LLC, see, e.g., Conn. Gen.Stat. Ann. § 34-133 (West 2005), he argued that the IRS did not have the authority to “unilaterally pierce the corporate veil of an LLC simple [sic ] by looking at how it reports it’s [sic ] income,” and that the IRS’s application of the check-the-box regulation was therefore “in direct conflict with the right of an LLC member.” (McNamee Request for a Collection Due Process Hearing.)

In a Notice of Determination Concerning Collection Action(s) Under Section 6320 and/or 6330, dated October 23, 2003 (“IRS Determination”), the IRS Appeals Office rejected McNamee’s appeal. The unpaginated explanatory Attachment (“IRS Determination Attachment”) stated that the IRS’s review confirmed that “[WFM-LLC] was set up as a single member LLC, and that you, as the single member, did not elect association status .... ” (IRS Determination Attachment, first page.) After discussing the pertinent Treasury Regulations, the IRS concluded that, “[therefore, the LLC has been disregarded as an entity separate from you. You, as the single member owner, are personally liable for the employment tax debt of the LLC” (id. third page). The IRS also noted that, while the administrative appeal was pending, McNamee had terminated the existence of WFM-LLC (see id.

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Bluebook (online)
488 F.3d 100, 99 A.F.T.R.2d (RIA) 2871, 2007 U.S. App. LEXIS 12016, Counsel Stack Legal Research, https://law.counselstack.com/opinion/sean-p-mcnamee-v-department-of-the-treasury-internal-revenue-service-ca2-2007.