George M. Steinbrenner III is the most powerful owner in sports. Baseball rewrote its collective bargaining agreement in 2002 for the purpose of getting its hands on some of his money, both to chip away at his power and to prop up the weaker clubs. So rich are Steinbrenner's Yankees that they will carry a $184.2 million payroll this season, unflinchingly write checks for approximately $70 million in revenue sharing and luxury tax, and—even figuring in the cost of such extravagances as flying their own groundskeeper to Japan—still make a tidy profit.
Steinbrenner is imperial, his empire impervious more than it is, as Boston Red Sox president Larry Lucchino infamously declared in December 2002, evil. Age has changed him. The fainting spell in Sarasota has changed him. All the funerals have changed him. He's softer around the edges, given to sudden jags of crying and even more than ever ridiculously charitable with his money. However, ruling over the Yankees—from personally ordering the signing of free agents Gary Sheffield, Kenny Lofton, Tom Gordon and Travis Lee last winter to banning chewing gum wrappers in the batting cage—fully remains his life's work.
"I'm happier than I've ever been," he says about running the Yankees. "It's the best we've ever had it."
And he has no intention of letting go. He has two sons, Hank, 47, and Hal, 35, and two daughters, Jennifer, 44, and Jessica, 40. Hank, Hal and Jennifer's husband, Steve Swindal, 49, serve as the Yankees' general partners. Steinbrenner has never spoken with any of them about a succession plan. "No, I never really have," he says.
It is a sensitive subject. He knows, his associates say, that his sons may not be interested in running the Yankees. Hank spends most of his time with his father's horse racing interests. He only dabbles in baseball, such as in 2002 when he argued at a meeting of Yankees baseball operations executives for the team to trade for overpriced Toronto Blue Jays outfielder Raul Mondesi, who turned out to be a bust. "The Yankees go out and make the big deal!" Hank told general manager Brian Cashman, who opposed the trade. "It's what the Yankees do!"
"I'm not sure Hank understands me," Steinbrenner says. "He does not like the turmoil that's around [an owner]. He chooses to not be too much in that. Hal I'm very proud of, because he's as tough as they come."
Anyway, who ever heard of a king retiring? "Well, I don't look for any point that I'm going to retire by this time or that time," he says. "I'm an old coot who will hang around. I'll be around for some time, as long as the New York fans want me. I hope they understand they're Number 1 with me. I care about New York dearly. I like every cab driver, every guy that stops the car and honks, every truck driver. I feed on that. That keeps me working hard to be able to afford to do the things that we do."
"For years he's talked about, 'Is it time to turn over the reins to the family?' " says Harvey Schiller, a former chairman and CEO of YankeesNets LLC and a friend for more than 25 years. "But it's hard for some people in his position. I liken it to entrepreneurism. When you've built up the business so well, it's not easy to let it go. And I don't think he should give it up."