AS Wall Street smackdowns go, this one’s a doozy.  Carl Icahn says William Ackman is ânow the young gunfighter who wants to show he beat the older gunfighter with a big reputation.â  Mr. Ackman now leads Pershing Square Capital Management. His long court fight with Mr. Icahn involved a relatively small 2004 deal.  In one corner is Carl C. Icahn, the corporate raider who made C.E.O.’s tremble back in the 1980s and, at 75, is still chasing deals.  In the other is William A. Ackman, 45, one of Mr. Icahn’s figurative heirs and a leading practitioner of the bruising, Icahnesque craft politely known as activist investing.  These ultrarich men battled for seven years in multiple courts, over a relatively paltry $4.5 million. That might be real money to mere mortals, but to these two, it’s barely a rounding error.  So why bother? This battle, it turns out, was more about big egos than big money — and it has left both men spitting expletives. The scrape finally ended this month, with Mr. Ackman victorious. But, before it was over, the affair occupied a Who’s Who of powerful lawyers and ran up millions of dollars in legal fees, all because of an otherwise forgettable deal the pair cut back in 2004.  “The guy is a shakedown artist,” Mr. Ackman sneers. “His word is worthless.”  Mr. Icahn says: “He’s now the young gunfighter who wants to show he beat the older gunfighter with a big reputation. He just likes pounding himself on the chest.”  In the secretive world of hedge funds, most money managers prefer to keep low. Not Mr. Icahn and Mr. Ackman. They are media hounds who court public attention and regularly star at investor conferences. Both buy stakes in companies and agitate for change. Both bemoan what they see as management failures and try to shame companies into replacing their C.E.O.’s, shake up their boards and do whatever it takes to bolster the value of their investments.  In many ways, this is a generational battle, a clash of old Wall Street and new Wall Street. Mr. Icahn may at times seem trapped in the 1980s, right down to his Gecko-esque blue shirts with white collars and cuffs. After 50 years in this game, he still seems to think that most companies would be better off if they would just listen to Carl C. Icahn.  Mr. Ackman is the smart-alecky boy wonder in a crisp modern suit and a Charvet tie. He, too, has become wildly rich, albeit without the old Icahn gruffness. After losing a battle against Target in 2009, he choked up during a speech in which he quoted Martin Luther King Jr. and John F. Kennedy.  When he first met Mr. Icahn in 2003, Mr. Ackman was virtually unknown outside Wall Street circles. It looked as if he might remain so. His world was falling apart. Gotham Partners, the hedge fund he helped to found when he was in his 20s, had just blown up. The Securities and Exchange Commission and Eliot Spitzer, then attorney general of New York, were investigating him. His investors wanted their money back.  So Mr. Ackman cold-called Mr. Icahn.  He wanted to sell Hallwood Realty, a company whose stock traded at about $60. Mr. Ackman believed Hallwood was worth $140 a share. “By reputation, I knew he was a tough guy and a difficult guy,” Mr. Ackman says. “I wanted to make sure I could collect.”  He continues: “I insisted the agreement be short. I also insisted it have a mathematical example in it, so that there could be no question about the intent of the agreement.”  That’s not quite the way Mr. Icahn remembers it. He says that he was the one who was worried, and that Mr. Ackman was under investigation and desperate to sell. (Both investigations were later dropped.)  “I checked him out,” Mr. Icahn says. “He was in trouble with the S.E.C.; he had investors leaving him. A few of my friends called me up and said; ‘Don’t deal with this guy.’ ”  Mr. Icahn says he saved Mr. Ackman’s bacon, although he puts it more colorfully. The two hammered out a contract. Mr. Icahn said he would pay Mr. Ackman $80 a share and offered a form of insurance. If Mr. Icahn unloaded his shares within three years, the two would split any profit above a 10 percent return.
Carl C. Icahn and William A. Ackman battled in multiple courts over a 2004 deal, though it involved a sum of money that might seem like small potatoes to them.