But the 49-year-old Dukeman can't help but be a little jealous of New England's younger generation, which missed the years of heartbreaks and watched Boston turn into the most successful sports town in the nation -- a city that has won a title in all four Major sports over a seven-year span, the first to have that much success.
"People now," he said, "these kids growing up, they think these sports teams in New England win all the time. They just think winning a championship is just part of being a sports fan in New England. We had pain, man."
But Dukeman has lived through it and come out with a smile. His job with the BoSox Club -- which, he assures you, is a volunteer gig (though with some pretty neat benefits) -- has been a "dream come true."
He's the top dog in a community that includes roughly 850 members. The club is meant to give inside access to the biggest of Red Sox fans; from those who have lived through the bloody sock to those who could only cringe as Aaron Boone's home run left Yankee Stadium.
Talk to Dukeman and one thing is evidently clear: Not only is he particularly passionate about his position, but he's forced it (at least he says) on his entire family.
"My kids were in bed sleeping with their Cowboy-Up T-shirts on when Boone hit that home run," he said, discussing the Red Sox's eventual loss to the Yankees in the 2003 American League Championship Series. "And I realized, 'Oh my God, when I wake up tomorrow I'm going to have to tell them [the Sox] lost -- just like I always have, and just like me my whole life. Now I'm going to be doing it to them. It's really happening.' I'm hanging this Red Sox thing on my kids."
It comes with the job. But it also has its perks.
Through the years, Dukeman has met the likes of Dustin Pedroia, David Ortiz, Pedro Martinez, Roger Clemens, Dennis "Oil Can" Boyd, Buck O'Neil, Fred Lynn, Rico Petrocelli and his personal favorite, Carl Yastrzemski.
"That's the coolest thing that's happened to me," Dukeman said. "Once we got through talking about all that happened to him as a player, we spent most of the time just talking about fishing and golf. He was great. And for me, as president of the BoSox, meeting Carl and some of the players from my childhood -- like Fred Lynn and Jim Rice, Rico Petrocelli, and all those guys. That's what it's all about."
Don't be fooled -- Dukeman does have a day job. He works for the Commonwealth of Massachusetts, in a job he chose not to identify, but when he does retire, it's all BoSox from there.
The events he so adoringly organizes are meant to enhance the experience of all the members. Each person pays $90 a year and spends a few bucks extra for tickets to each event. But the club has just one stipulation to enter: You have to be a Red Sox fan.
As far as Dukeman knows, the club is the first of its kind. The Indians have a fan club, but it operates differently. Dukeman's job is to make sure everyone that's part of the club has one heck of a time being in it. And, oh yeah, meeting Hall of Famers isn't too bad either.
It's a job Dukeman hopes to never lose. And whether they like it or not, his family members are coming along for the ride.
"It's part of the package with me and the Red Sox," he said. "My wife knew what she was getting into. We've gone down to Spring Training since we've had kids and she enjoyed it. We brought our children up the right way."