When Tokio Marine Holdings Inc. sought to enter U.S. life insurance -- uncharted territory for the Japanese insurer -- it turned to the same attorneys and bankers that walked it through its first U.S. insurance deal in 2008. Macquarie Group Ltd. and Sullivan & Cromwell LLP advised Tokio on its $2.66 billion acquisition of Delphi Financial Group Inc., announced in late December.

The Delphi acquisition is part of Tokio's broader international expansion, which began in 2008 with its $696 million purchase of Lloyd's of London insurer Kiln Group Ltd. and its $4.7 billion deal for Bala Cynwyd, Pa.-based property and casualty insurer Philadelphia Consolidated Holding Corp. Fox-Pitt Kelton Cochran Caronia Waller's John Waller and Ian Brimecome advised Tokio on those deals, and Macquarie inherited the Tokio relationship after acquiring Fox-Pitt in late 2009.

Macquarie's James Anderson, Pete Nero and Anthony Schwartz -- all former Fox-Pitt bankers -- represented Tokio on Delphi. Anderson had been providing Delphi with advice since 2005, which proved helpful when his team began working with Tokio last summer to help it narrow its acquisition focus. "I knew the [Delphi] business and the footprint of the U.S. business," he says. Delphi fit nicely with Tokio's Philadelphia Consolidated unit. "There was no overlap in the businesses, no redundancies, and the customer base was similar," presenting cross-selling opportunities.

Robert DeLaMater and Melissa Sawyer led the Sullivan & Cromwell team on the Delphi deal in New York, and Izumi Akai and Keiji Hatano provided counsel in Tokyo. DeLaMater says the firm's ties to Tokio date back almost two decades. DeLaMater spent three years in Sullivan's Tokyo office in the 1990s, helping Tokio Marine on a Japanese online brokerage joint venture with Charles Schwab & Co. in 1999. Sullivan & Cromwell also worked on "smaller, more discreet corporate and securities law questions" for Tokio, he says.

Sullivan & Cromwell, says DeLaMater, represented J.C. Flowers & Co. LLC when it sold Fox-Pitt to the Aussie bank for $147 million in September 2009. For Delaware corporate counsel, Tokio hired Richards, Layton & Finger PA.

Wilmington, Del.-based Delphi, for its part, selected its longtime counsel for its sale to Tokio, receiving legal advice from Morris, Nichols, Arsht & Tunnell LLP's Rick Alexander and James Honaker. The firm's relationship with Delphi began when associate Chad Coulter left to join the insurer in 1991. He became Delphi's general counsel in 1998.

Representing the special committee at Delphi were Scott Barshay, Andrew Thompson, Lauren Angelilli and Eric Hilfers of Cravath, Swaine & Moore LLP. Delphi founder, chairman and CEO Robert Rosenkranz, who holds just under half of the company's voting rights, took legal counsel from Cleary Gottlieb Steen & Hamilton LLP's Daniel Sternberg, Paul Shim and Arthur Kohn. The Delphi special committee used Lazard's Al Garner, Gary Parr and Joseph Cassanelli for financial advice, representing the investment bank's first mandate for Delphi. -- Michael Rudnick

Both new and old faces surfaced to advise acquisitive Gilead Sciences Inc. on its largest deal yet, the $11 billion purchase of Pharmasset Inc., announced in late November. But one face noticeably absent was Dewey & LeBoeuf LLP's Richard Climan, who had counseled Forest City, Calif.-based Gilead on some of its largest deals, including its $1.4 billion purchase of CV Therapeutics Inc. in 2009 and its $2.5 billion deal for Myogen Inc. in 2006. Climan handled those deals while with Dewey and Cooley Godward Kronish LLP, which he left in 2009.

Gilead turned to Skadden, Arps, Slate, Meagher & Flom LLP's Stephen Arcano, Brandon Van Dyke and Franklin Gittes for this latest deal. Skadden may have been tapped due to its recent work counseling Gilead on debt offerings. The Pharmasset acquisition included $6.2 billion in debt financing, the first Gilead acquisition in at least a decade with significant debt. Skadden knows Gilead's debt structure, having worked on a $2.2 billion convertible note offering in July 2010 and a $1 billion senior note offering in March. Sullivan & Cromwell LLP's Matthew Hurd, who led the team that advised Pharmasset, praises Skadden on its inaugural Gilead deal. "Skadden had to both negotiate a deal with us and negotiate financing -- all in a very compressed time frame," he says.

The sale to Gilead marks Sullivan's first mandate for Princeton, N.J.-based Pharmasset, which had not done any deals in its 13-year history. Pharmasset approached the firm in late summer to examine strategic alternatives including remaining independent, Hurd says.

Hurd's team includes Krishna Veeraraghavan, Hydee Feldstein, Neal McKnight, Nader Mousavi, Ronald Creamer, Matthew Friestedt, Matthew Brennan, Richard Urowsky and Brian Frawley.

Morgan Stanley's Steven Harr, Jessica Chutter, Susan Huang and Ari Terry provided Pharmasset financial advice, helping it reel in a $137 per share price tag, an 89% premium to its close the prior trading day. Pharmasset's pipeline of hepatitis C treatments helped its shares climb from $10 in January 2010 to nearly $132 at the end of August.

For financial advice, Gilead turned to Barclays Capital's Jed Brody and Matt Young and Bank of America Merrill Lynch's Ivan Farman, Edmund Baxter, Robert Glassman and Matt Panuwat. Barclays and BofA also provided debt financing for the deal.

BofA's Alan Hartman and Mark Robinson, both now with Centerview Partners LLC, advised Gilead on the 2009 CV Therapeutics acquisition, sitting across the table from Barclays' Frederick Frank, now with Peter J. Solomon Co., and Young.

While Barclays has not worked on any deals for Gilead until now, it has been involved in its debt financings. -- M.R.