Hitmen for Hire

With two outs in the top of the seventh, slow-pitch softball's final inning, Gregg Connell approaches the plate with his team in an unfamiliar position: They're about to lose. It's a drizzly April day in Florida, and the best teams in the country have assembled at Osceola County Stadium, the Houston Astros' spring training facility, for the first big company tournament of the season. Connell, a 28-year-old bull of a man, drives the ball 400-plus feet for a triple, giving his squad, Resmondo, a 21-20 lead over Art Explosion. When I ask Connell about his clutch hit later, he shrugs his massive shoulders: "That's what I get paid to do."

He's not joking. Ostensibly, softball is an amateur sport. That hasn't stopped Travis Resmondo, a 37-year-old multimillionaire purveyor of sod throughout Florida, from paying each of his players up to $60,000 annually. If Resmondo fields the company softball equivalent of the Yankees, archrival Dan Smith, a 64-year-old California construction magnate, runs the Red Sox (though the team is known simply by his name). Each spends more than $500,000 per year on his team, more than double the closest corporate competitors. In the past decade, Resmondo has won five United States Specialty Sports Assn. World Series. Smith has won four. "It's sort of like Tiger and golf," says Don DeDonatis, who heads the USSSA, softball's largest organization. "If Resmondo and Dan Smith aren't at the tournament, nobody comes."

There's a downside to dominance, though. When Connell—who works full-time as an electrician—hits his clutch triple, the only cheers come from the Resmondo dugout. There are no kegs and virtually no fun. Just paid professionals doing a job.

The origins of softball can be traced to Thanksgiving Day at Chicago's Farragut Boat Club in 1887, where Harvard and Yale alumni had assembled to hear the results of the schools' annual football game. A Yalie tossed a boxing glove at a Harvard grad, who batted it away with a broom handle—a Eureka moment for George Hancock, a reporter on the scene who improvised a set of rules for a new game based on baseball.

By the late 1970s, 40 million Americans were playing softball, and companies spent lavishly on their teams. Steele's Sports, an Ohio sporting-goods manufacturer, fielded that era's equivalent of Resmondo—with one key difference. "We all worked for Steele's," says Mike Macenko, 54, a "Men of Steel" veteran who played first base. "When we weren't playing softball, we were doing deliveries and sales."

About 20 years ago tax laws changed so that companies could no longer write off softball expenditures as expenses. The number of well-funded corporate teams swiftly dropped, leaving the field wide open for a few softball-crazed entrepreneurs willing to spend hundreds of thousands of dollars each year to win the nation's top amateur tournaments, just for their own satisfaction. There are several, often feuding, governing bodies of softball, presiding over more than 100,000 sanctioned teams, not including the casual corporate, church, and social leagues that bloom each spring. The elite level, though, is an entirely separate universe. Players for Dan Smith and Resmondo live across the country and are flown in solely to play ball. Many work in the sporting-goods industry, while others are schoolteachers and construction workers. "Resmondo and Dan Smith are teams of hired guns," says Gene Smith, publisher of Softball Magazine.

The situation strikes even veteran players as odd. "I thought softball was about having a six-pack in the parking lot," says Jeff Wallace, a catcher who has played for Resmondo for 11 years.

As the top level of the game has been professionalized, the grass roots have withered. Only 12.8 million Americans play softball, according to the National Sporting Goods Assn., a sharp decline that Ron Radigonda, executive director of the Amateur Softball Association of America, USSSA's main competitor, chalks up to demographics. "The baby boomers grew the sport," he says, "and now they're in their 60s." Others blame technology. "With the composite bats, a 150-pound guy can hit a softball 400 feet, easy," Macenko says. "At the same time, they've doubled the compression of the balls, which are as hard as croquet balls, to make them go faster and farther." The result is that pitchers are sitting ducks for lethal line drives. Most pitchers in Osceola wore masks, and some batters target opposing players. "Who wants to deal with that?" Macenko says. "Why wouldn't you just play soccer or go bowling?"

Resmondo surrenders a home run in the bottom of the seventh. With the composite bats, homers are so common that the USSSA sets a limit of 16 per side for the top division, and sluggers don't even have to round the bases (though some of them could really use the cardio). It's double-elimination, and Resmondo wins its next two games before losing to the team sponsored by sporting-goods manufacturer Combat Sports. Jon Oram, who spent seven years in the Cleveland Indians minor-league system, hits the game-winning homer for Combat. Afterward, he concedes that his team got lucky. "Seven out of 10 times, Resmondo's going to beat us," says Oram.

Travis Resmondo was working and couldn't see his half-million-dollar dream team go down in person. When I call to check on his spirits, he isn't upset. The team is still fiddling with its roster, trying out new players such as Vernand Morency, an ex-minor leaguer who also played in the NFL for the Green Bay Packers.

Dan Smith goes on to take the trophy, just as it did last year (though Resmondo then dominated the rest of the 2009 season). Travis Resmondo told me he once threw an ice cream cone into Dan Smith's dugout to rub in a victory. The owners are fierce enemies.

They're also the last of a vanishing tribe. The ASA recently canceled its top division to eliminate juggernaut teams such as those of Resmondo and Smith, and there is no sign of another businessman willing to match their financial commitment. So someday, maybe not too far off, softball could revert to its old-fashioned form. Resmondo says he'll eventually step away from the sport. But not yet. "It's an ego thing," he says. "I wish we'd never lose."

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