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Jeremy Spector’s practice involves tax planning, IRS controversy work, and the structuring of corporate transactions, with particular emphasis on advising professional sports leagues and teams and on representing large taxpayers through the IRS audit, Fast Track, and Appeals processes.

Mr. Spector has been ranked as a leading tax lawyer in the Legal 500 US for his “superb legal advice and practical business guidance," by Chambers USA, which has noted his practice’s “dominant presence in the sports industry,” in Who’s Who Legal: Sports & Entertainment, and as a Law360 MVP. He is co-chair of the firm’s sports practice and a vice-chair of its tax group.

Representative clients in the sports world include the National Football League, Major League Baseball, the National Basketball Association, the National Hockey League, Major League Soccer, the UFC, Fenway Sports Group, the United States Olympic Committee, and dozens of professional sports clubs.

  • Secured a “no change” letter from the IRS Examination division after its challenge to the economic substance of a taxpayer’s $1.1 billion financing program.
  • Settled an Appeals case regarding a franchise owner’s built-in gain upon the sale of his franchise, with the taxpayer receiving a multi-million dollar refund from the government.
  • Advising the National Hockey League on domestic and cross-border tax, corporate, and intellectual property issues related to the creation of the NHL Network, and, separately, the NHL’s business activity outside North America.
  • Representation of an MLB club in a $300 million dispute with the IRS regarding the club’s affiliated cable network.
  • Currently representing approximately a dozen professional sports franchises in IRS audits.

Tax Controversy Matters

  • Persuaded a state Department of Taxation to reverse its long-held, industry-wide position regarding sports clubs’ apportionment methodologies and to consequently drop 14 separate club audits.
  • Representation of an NFL club in a $275 million dispute with the IRS regarding stadium financing, player contracts, and broadcast agreements.
  • Obtained reversal of an IRS Chief Counsel Advice memorandum regarding the tax treatment of a league-wide disability insurance program.
  • Lobbied the Treasury Department on a client’s fringe benefit issue, resulting in an example being inserted in new regulations adopting the client’s facts and proposed legal conclusion.
  • Secured “no change” letters in income tax audits of two sports leagues and three leagues’ for-profit affiliates (five separate audits).
  • Negotiated an extremely favorable industry-wide settlement with the IRS National Office regarding the tax treatment of acquisitions of professional sports franchises and related assets.
  • Successfully resolved Fast Track appeal of a communications company’s tax treatment of a governmental fine, based on a novel legal theory and resulting in the deductibility of the majority of the fine.

Tax Planning Matters

  • Structuring John Henry’s sale of the Florida Marlins and his simultaneous acquisition (as lead investor) of the Boston Red Sox, Fenway Park, and NESN as a tax-free like-kind exchange.
  • Representation of multiple NFL clubs regarding their respective billion-dollar stadium development projects. Issues include structuring club and league real estate and financing transactions, use of tax-exempt bond financing and personal seat licenses, coordination among affiliated taxable and tax-exempt entities, and counseling on transaction documents (leases, management agreements, etc.).
  • Representation of the NFL and other sports leagues in tax, corporate, legislative, and PR matters related to the relinquishment of their tax-exempt status. Projects involved tax planning, meetings with IRS executives and members of Congress, and coordination of audit defense strategy.
  • Advising Roush Fenway Racing on driving and endorsement agreements with Cup Series drivers, and advising Major League Soccer on marketing deals with its players.
  • Advice regarding franchise transfers, including Chris Cohan’s sale of the Golden State Warriors, the NHL’s purchase and sale of the Phoenix Coyotes, Major League Baseball’s relocation and sale of the Montreal Expos, Fenway Sports Group’s purchase of a 50% interest in Roush Racing, and the USTA’s acquisition of the Western & Southern Financial Group Masters tournament.
  • Drafting World Baseball Classic agreements with leagues, federations, venues, and players.
  • Counseling clubs and all five leagues on crafting and drafting bonus and deferred compensation arrangements for players and front-office executives, including with respect to Section 409A issues.
  • Representation of the NBA, NHL, and NFL regarding their pre-season, season-opening, and other regular season games in Europe, including the foreign tax consequences to players and teams.
  • Establishing multi-entity, multi-jurisdictional organizational structures for leagues’ taxable and tax-exempt activities, including charities and foundations.
  • Continuing advice to Sotheby’s on the sales and use tax ramifications of auctions.
  • Legislative and strategic advice to Amazon.com regarding the state taxation of online sales.
  • Advice to various broadcast stations and their private equity owners regarding station acquisitions and related marketing agreements.

Pro Bono

  • Foundation for All DC Families, Catholics for Equality, Marylanders for Marriage Equality, and Human Rights Campaign – Tax and corporate advice to these organizations that engage in both non-partisan research regarding same-sex marriage and legislative advocacy supporting marriage equality.
  • Funders Together to End Homelessness – Tax and corporate advice to this entity that serves as a national network of philanthropic funders.
  • Community Tax Aid, Inc. – Representation of the Board of Directors of this low-income tax clinic in front of the IRS regarding a federal grant received by the organization.
  • Georgetown Children’s House Endowment and Washington Child Development Council – Tax, governance, and general programmatic advice to these organizations that promote quality child care and childhood development in the District of Columbia.
  • Law360, Tax MVP (2017) 
  • Chambers USA, Tax (2020) and Sports Law (2014-2015)
  • Legal 500 US, Tax - US Taxes (2013-2017)
  • Legal 500 US, Not-for-Profit (2013-2017)
  • Legal 500 US, Sports (2014-2016)
  • Legal 500 US, Tax: Tax Controversy (2012, 2014-2015)
  • Legal 500 US, Telecoms and Broadcast: Transactional and Tax (2012)