ESPN Sprint Cup

October has been a stressful time on Yawkey Way, even more nerve-racking than most sports fans realize. To truly appreciate the blood pressure levels, you need only to take a look back at Saturday night.

As the clock chimed in the 11 o'clock hour, the Boston Red Sox were scrambling to rally from one run down and force their American League Championship Series Game 2 matchup with the Tampa Bay Rays into extra innings. While Sox owner John Henry kept one eye on the game in Florida, he was also glued to ESPN and the goings-on in the Bank of American 500 at Lowe's Motor Speedway in Charlotte.

That's where Roush Fenway Racing co-owner Jack Roush was coaching three of his five race car drivers -- Jamie McMurray, Greg Biffle and David Ragan -- into position for a potential race win, all the while asking for scoring updates from Tropicana Field.

By night's end only McMurray was able to crack the top five, and teammate Carl Edwards, dogged by mechanical problems, dropped from second to fourth in the Chase for the Cup standings.

Ninety minutes later the Rays scored the winning run in the bottom of the 11th inning.

"Hey," exclaimed Edwards, an admitted text-message buddy to several members of the Sox, "I'd rather be a championship contender and have a bad night than not be a contender at all."

Welcome to the wild life of the Fenway Sports Group, where stick-and-ball and tire-and-oil manage to work hand in hand. And Saturday's results notwithstanding, they do it pretty darn well.

I pronounce you Jack and John
On a chilly February '07 night at Jackie Robinson Park in Daytona Beach, Henry and Roush made the announcement heard 'round the NASCAR world. Henry and his Red Sox co-owners had purchased 50 percent of one of stock car racing's genuine superpowers -- the five-car, two-time Sprint Cup-winning operation of Roush Racing. The purchase took place through the Fenway Sports Group, a still-new Sox spin-off corporation in search of fresh opportunities and undiscovered revenue streams (hey, someone's got to pay Dice-K's salary). FSG, led by Sox executive Mike Dee, had already ventured into the PGA Tour with Boston's Deutsche Bank Championship, college sports with Boston College and the ACC, and the new frontier of online sports via a partnership with MLB.com.

Now it was in the NASCAR business, steered there by motortsports-mad John Henry.

In the nearly two years since, the rest of the monkey-see, monkey-do Cup garage has scrambled to follow suit, frightened yet intrigued by the idea of bringing on an ownership partner. Of course, the idea of those partners brining a likely influx of capital didn't hurt.

Most of those reactive deals have either failed to produce (Gillett Evernham Motorsports, where you at?), have yet to get going (Petty Enterprises + Boston Ventures = ?), or simply fell flat on their face (Ginn Racing, we hardly knew ye).

But Roush Fenway Racing has not only survived, it has thrived. Since the merger, its five Cup cars have won 15 races with four different drivers and the team has added wins across the lower divisions, including a 2007 Nationwide Series title with Edwards. Communication between Boston and Concord, N.C., has overcome every potential roadblock, revenues have held steady during brutal economic times, and the team has three cars in the '08 Chase and a fourth with a solid lock on 13th, aka Best Non-Chaser. And, oh yeah, the baseball team has been pretty good, too.

Not bad for a deal some industry wags predicted was destined for divorce.

"I think we approached it the right way from the beginning," said Roush Fenway Racing president Geoff Smith, who oversaw the merger from the NASCAR side. "We were very meticulous when we put the deal together. I joked that we all had to submit DNA samples before the partnership was approved. From the start we were all very careful to understand how the baseball people had been so successful at their jobs and they were curious to know how we had been able to achieve some success in racing. Nobody came in telling anyone else how to do their jobs. We learned from one another."

Curves and curveballs
What's being shared and taught has had nothing to do with pitch counts or gear selections. It's all about address books. The sales and marketing teams are constantly swapping names and ideas, eager to leverage relationships on one end to create new opportunities on the other.

"What John [Henry] believes in are big brands," explained Sam Kennedy, the Red Sox senior VP of sales and marketing, as he walked into Fenway Park for Game 4 of the ALCS. "We looked at other NASCAR teams to be involved with, but we kept coming back to Roush Racing. John has been a huge race fan for years and he knew that Roush was second to none when it came to performance and running its business."

When Henry cold-called Jack in the Hat in '06, even someone as singularly focused on racing as Roush realized the benefits of the Red Sox logo.

"I was not in need of cash," he said over the weekend in Charlotte. "I did not need to do this deal to pay my bills. But in a volatile sponsorship market the partnership made sense. And the northeast is really the last untapped market for potential NASCAR fans. What better way to reach them than through the Red Sox?"

NAS-CAH
Though still in its infancy, the sharing of Rolodexes has already led to new partnerships. Edwards now defends his house wearing Under Armour, a deal brokered through the apparel company's existing relationship with the Red Sox.

Ragan's sponsor, AAA, is now also a major client for the ballclub. Fenway Park hosts NASCAR weekends in conjunction with race weekends at New Hampshire Motor Speedway, the Sox (and corporate partner Lumber Liquidators) have ridden on the hood of the 99 Ford, and every home game features Roush Fenway Racing updates on the big screen between innings.

Every weekly FSG sales meeting includes Roush Fenway Racing coworkers, and U.S. Airways will be able to keep its Boston-to-Charlotte flights on the schedule thanks to a constant haul of staffers shuttling back and forth from New England to North Carolina.

If this fall has been any indication, those flights are also becoming increasingly packed with newbie NASCAR fans, anxious to visit the Charlotte race shops and the track in Loudon, N.H., all donning Roush Fenway hats and shirts.

"It's exciting to see New Englanders become so excited about racing," said new FSG Executive VP Brian Corcoran, who certainly knows of what he speaks. The New Hampshire native's career took him down pit road, serving as NASCAR's managing director for corporate marketing. Now he can't believe he's getting paid to go to his two offices -- one across the highway from Lowe's Motor Speedway and the other in the shadow of the Green Monster.

"There's a buzz about NASCAR that there's never been in this region before and I know it is because of Roush Fenway Racing. I have baseball fans come to me and say, 'I'm a big Matt Kenseth fan because he's one of our Red Sox guys.' Mr. Henry likes to say we're winning the region's millions of Red Sox fans over to NASCAR one by one, including the players. At the same time we're winning some race fans over to Red Sox Nation, including the drivers. I really think that's happening."

As October rolls on, Fenway Sports Group will keep working to convert the congregation, one lap and one at-bat at a time. Even if it means more of those long, tense nights.

Ryan McGee, a senior writer for ESPN The Magazine, is the author of "ESPN Ultimate NASCAR: 100 Defining Moments in Stock Car Racing History." He can be reached at mcgeespn@yahoo.com.