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Alexander Lynch at Brobeck, Phleger & Harrison could be considered one lucky guy. The New York-based partner bagged for Brobeck the initial public offering of Playboy.com, the online content operation of Hugh Hefner’s specialty publishing and entertainment empire. Playboy.com, based in Chicago and headed by Hefner’s daughter, Christie, is seeking to raise $50 million. And like any other high-profile Internet offering, another Silicon Valley firm will be seated across the table. Representing the underwriter is Jay Hachigian, a Gunderson Dettmer partner. The circuitous route that delivered the deal to the firms hasn’t yet been unraveled, but it appears to hinge on connections in the New York investment banking scene.

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