ESPN Sprint Cup

Tonight has officially become tomorrow morning.

John W. Henry really needs to turn off his computer, stow his steering wheel next to the pedals under his desk and hit the sack. Or if the billionaire owner of the Boston Red Sox insists on spending these wee hours online, he could at least scan the West Coast box scores or, as one of the lead dogs of modern hedge funds, figure out a way to turn around his struggling investment firm. Yeah, he thinks, I'm shutting it down now.

But he doesn't. A new challenger has logged on, trolling for a battle on the digital high banks of Bristol. One more race. OK, maybe two.

Henry is a capitalist god, a 57-year-old self-written success story. In financial circles he was once described as a "numbers genius" after earning billions for investors by deciphering the global futures market. In baseball circles, he's the owner who earned a ring in only his third season with a team that hadn't won one in 86 years. But late at night, when no one else is around, he shelves all concerns about lagging funds and nagging Steinbrenners, focusing only on making it around Thunder Valley with all four fenders intact on his virtual race car.

"I have the whole setup. Three screens, steering wheel, shifter, you name it," Henry says, describing a tricked-out simulation station. Henry loves the product so much, he bought the company that designed it and renamed it iRacing.

A few years ago, he added actual racing to his virtual hobby, tuning into NASCAR Nextel Cup races every Sunday afternoon. He fell in love all over again and, because he can, again bought the company (OK, half of it): Roush Racing, one of stock car racing's most successful outfits.

Roush Fenway Racing is the first major partnership between two big league organizations. Built on the vows of revenue streams and marketing gains, this marriage already has produced its double-take moments. But Matt Kenseth and Tim Wakefield playing catch in Daytona and Jamie McMurray and Josh Beckett joining each other's IM buddy list isn't why the deal was struck.

In the end, the goal was faster race cars and a stronger 40-man roster. And it has already forced rivals in both arenas to take notice.

"I don't know about baseball, but NASCAR has always been monkey see, monkey do," says Kyle Petty, driver-owner of Petty Enterprises. "Roush has made plenty of moves in the past we all thought were crazy. Well, now we're all doing what he was smart enough to pioneer. I bet if the Red Sox end up with a lot more money than everyone else, all the ballclubs will start to show up at the racetrack."

Unlikely partnership
Like John W. Henry, Jack Roush is an empire builder. The 55-year-old fedora-wearing motorsports mogul, a.k.a. "the Cat in the Hat," has won more than 250 races and four championships in NASCAR's top three series. A month after the Sox ended their near-century of frustration on the bloody right sock of Curt Schilling, Roush won his second straight Cup, on the heavy right foot of Kurt Busch.

The lead dog and the cat. Looking back, the unlikely partnership makes perfect sense. Looking forward, the impact looks downright scary.

"It's one thing to bring in a financial partner to help offset the out-of-control costs of racing," says Felix Sabates, who owns pieces of the Charlotte Bobcats and Chip Ganassi Racing. "It is something else entirely to bring in a high-profile partner with new ideas on how to market your team and how to recruit sponsors and who, just by adding his name, hands you a base of new fans."

In the spring of 2003, Roush and the Red Sox were in strikingly similar situations. Each belonged to leagues dominated by two-team rivalries -- NASCAR by Roush and Hendrick Motorsports and Major League Baseball by the Sox and the Yankees. Each had been the lovable loser, the one who always fell flat once the leaves turned colors. More to the point, Fenway Park was out of corners in which to cram seats and billboards, while Roush was running out of race cars with which to attract sponsors. So, as the Yanks and Hendrick stockpiled talent, the lead dog and the cat began separate searches for more dollars. One day, Roush answered Henry's cold call.

He listened intently as Boston's owner talked about how selling the Roush brand to only 10 percent of the 14 million Red Sox fans would create an unprecedented foothold in the region. Sure, it would take longer to assimilate all of Red Sox Nation, but wouldn't it be worth it?

Henry was preaching to the choir. These people loved race cahs, Roush had long believed. They just needed someone to root for. The six New England states are home to nearly 50 short tracks and have produced more than 40 current Nextel Cup crew members. A ticket on race weekend at the New Hampshire International Speedway is as difficult to score as a seat atop the Green Monster. Richard Petty and Bobby Allison both won Cup races in Oxford, Maine, of all places.

To Roush, the Northeast had long been NASCAR's last frontier. "Our fan base has covered a lot of areas," says Roush Fenway driver Carl Edwards, who grew up a Cardinals fan. "I'm from Missouri, and so is Jamie. Greg Biffle is from Washington, Matt Kenseth is from Wisconsin and David Ragan is from Georgia. But I think everyone in NASCAR knows the big untapped market is the Northeast. And there's no better avenue into New England than the Red Sox."

The deal was done by the start of the 2007 season but only after a grueling process that Roush Fenway president Geoff Smith describes as "everyone having to submit a genetic sample for testing." Henry's Fenway Sports Group purchased its share of Roush Racing for a price believed to be in the $60 million range, a number big enough to shake the financial foundations of a Cup garage, but barely enough to earn a get-to-know-me lunch with Dice-K. "The garage perception was that Jack Roush had to find some outside money to keep going," Smith says. "But we didn't need a group to underwrite our team to keep afloat. They invested only because it makes business sense."

That's not to say there aren't other NASCAR teams that need capital infusions. In fact, courtships of investors had begun long before the Roush Fenway union. Perennial also-ran MB2 Motorsports became an overnight contender after it was bought by golf resort mogul Bobby Ginn, who used his cash to lure Mark Martin from Roush. Richard Childress Racing was helped back into the upper echelon by what Childress describes as "a small group of outside backers."

But just as the gap has grown between the Yanks and the Sox and the rest of baseball, rival NASCAR owners also fear the repercussions of the rich becoming richer. Monkey see, monkey do: The next big deal is expected to be announced by summer's end, when Ray Evernham's three-car operation becomes part of George Gillett Jr.'s sports empire, a portfolio that includes the Montreal Canadiens and Liverpool FC of the English Premier League.

"Outside investment is not a new concept," Evernham says. "But after the Roush deal, we've seen an increase in the profile of potential investors. I said I was looking for a partner, and the phone has been ringing since. Whether it's one large investor or taking a team public, we are about to see a huge change in the NASCAR ownership landscape."

Adds Mike Dee, Red Sox COO: "I kid that it's like Trading Places. 'The Dukes are cornering the market on orange juice! Let's get in!'"

Learning curve
Aftershocks of the deal may already be shaking Nextel Cup front offices, but they have yet to be felt in the pit stalls of Roush and the clubhouses at Fenway. Both sides continue to sift through details, jetting between Boston and Charlotte to discuss how one side can best help the other. Sales staffs are sharing contacts, and Fenway marketing specialists are lending expertise to sell Roush's NASCAR more effectively to children. And accountants are figuring out how to divvy up the eventual profits between those shopping for left-side tires and those looking for left-handed relievers.

Still, the merger was apparent to every Sox fan at the homestand against the Rangers on the last weekend in June, the same weekend of the Lenox Industrial Tools 300 at the New Hampshire International Speedway. Roush Fenway showed off its fleet all around the ballpark, where it glimmered alongside the World Series banners and peanut vendors, turning Yawkey Way into Pit Road. Fans in Big Papi jerseys cheered as Carl Edwards threw out the first pitch (his heater impressed catcher Jason Varitek) and Roush Fenway drivers stood shoulder-to-shoulder with the Sox starting rotation and discussed strategy with Terry Francona.

Of course, that's all window dressing, secondary to the critical questions: Will longtime baseball fans want to learn about track-bar adjustments? And will career gearheads be compelled to brush up on the infield-fly rule? Those who know the lead dog and the cat, who have already celebrated wins over Barry Bonds and Jeff Gordon on the same day, aren't betting against them. "I had dinner with one of our limited partners the other night," says Dee, "a 68-year-old Bostonian who never paid attention to NASCAR in his life. He said, 'I gotta tell ya, I can see the appeal. I flipped by and stayed on it. I enjoyed watching it.'"

One down. 13,999,999 to go.

While Roush Fenway Racing works to win over New Englanders, here's how the rest of NASCAR can make its own friends in the Northeast Corridor.

• Produce a local hero -- Jersey's own Martin Truex Jr. is the new face of DEI, but there is plenty of room for another tristate rep -- and plenty of guys for the job. "There's a ton of talent up there," says Greg Zipadelli, Tony Stewart's Connecticut-born crew chief. "The right kid just needs the same kind of opportunity Martin had." Smart money's on Gibbs Racing's Joey Logano, a 17-year-old from Middletown, Conn.

• Clean up Watkins Glen -- The France family's road course is nestled in New York's scenic Finger Lakes region. But muddy parking, view-blocking pines and a confusing maze of chain-link fencing make attending a race there an unpleasant adventure.

• Make the Meadowlands happen -- "We have our awards banquet at the Waldorf," says Dale Earnhardt Jr., "but the only way we'll show New York City what we're about is to race there. Hell, shut down Times Square, and we'll race there." Surely, Junior would settle for the proposed 1.25-mile oval that would ring the Meadowlands horse track across the Hudson.

• Shorten the 24 Hours of Pocono -- If NASCAR wants New Yorkers to make a two-hour drive, Pocono Raceway must cut its Cup races from 500 miles to 400. Nothing turns off new fans like a midrace nap.

• Marry models and move to Manhattan -- Hey, it works for Jimmie (who rents) and Jeff (who owns), two guys who are seen at the city's trendiest troughs. "When I first saw Jeff Gordon, I was like, What's he doing in here?" says Jay-Z. "Now it's no big thing. He's a New Yorker."

Ryan McGee, the editor-in-chief at NASCAR Images and a motorsports writer for ESPN The Magazine, is the author of ''ESPN Ultimate NASCAR: The 100 Defining Moments in Stock Car Racing History.''