I met Jimmy Connors about 17 years ago, when I was an underage drunk.

He was playing in the annual tennis tournament at Carter Barron, an event then called the DC National Bank Classic. Not only was Connors one of the top players in the world at that time, but his athletic and verbal brashness on the court also made him stand out on the historically staid circuit (John McEnroe wasn’t yet good enough to showcase his dickhead routine). I wasn’t big on tennis, but I went to the match because I thought Connors was pretty cool. Those positive sentiments, however, didn’t stop me and my equally bombed buddies from heckling Connors all night long. “Where’s the centerfold, Jimbo? Didja bring the centerfold?” we yelled again and again and again, referring to the top seed’s wife, a Playboy playmate of the year in the 1970s. Ha ha ha! Belch belch belch!

Our buffoonish display inspired Connors to call us out of the crowd at the end of his match. Not to kick our asses, but to reward us for our pep. We accompanied him to a press conference, and he talked event organizers into giving us VIP passes for the entire tournament. We, of course, abused the privilege from the moment it was granted, cadging as much free food and booze as we could tolerate for the rest of the week.

The Connors encounter and other blotchy recollections of my wasted youth took up most of my thoughts last Friday evening. Connors was making his first appearance in the area since becoming involved with a fledgling tennis circuit for seniors for which he serves as both co-owner and featured attraction. Even at 43, Connors still has drawing power: Tickets for his opening match at the Corel Champions tournament at tony Woodmont Country Club in Rockville—with a face value of up to $50—were sold out. A lot of people who showed up were, like me, looking back.

Looking back, after all, is the whole reason the seniors tour exists. America’s nostalgia boom certainly isn’t limited to the sporting scene. Baby boomers have lots of disposable income, so concert schedules at large arenas and amphitheaters are top-heavy with pop acts from the 1960s and ’70s. Madison Avenue decided to have Ronald McDonald grow up in order to put the touch on boomers.

But the trend toward oldies acts in sports is particularly profound—and distressing. Blame it on George Foreman, but every boxer from the last two decades except Duk Koo Kim is lacing up the gloves again. And pro golf, which competes with tennis for country clubbers’ affection, has a thriving seniors tour. Golf translates more smoothly to middle age. As long as guys like Nicklaus and Palmer still have their swing, all tournament organizers have to do is move the tees up 15 yards, make the pin placements a little less challenging, and nobody’s the wiser.

Connors admits he decided to launch a seniors tennis tour after seeing how well it worked in golf. And there is definitely a void in men’s tennis today. The personalities parade that Connors led in the mid-1970s included the hunky Bjorn Borg and nasty boys Ilie Nastase and McEnroe; in recent years the “real” circuit has been dominated by big, strong stiffs like Jim Courier and Pete Sampras. Even worse, the game of tennis itself has gone south. High-tech equipment and weight training have created a generation of guys who bang winners on serves or after just one volley. I’ve seen dart matches with more sustained back and forth. The men should take a lesson from the women’s tour, which has flourished because women still volley and there is a lot of intriguing personal subtext. Not coincidentally, there isn’t any talk of starting up a circuit for 35-and-over females.

But in the absence of any drama on the men’s tour, Connors’ creaky glory looks pretty good. Connors’ opponent Friday was John Lloyd. Way back when, this would have been a steamroll job. Connors had 125 career wins on the pre-Depends tour; Lloyd had one. To tennis fans, the only link between the two is that they both used to be engaged to Chris Evert; Lloyd, at 42, is still in the public eye because he actually followed through and married her. But even though Lloyd was never in Connors’ class, the aging process has a way of leveling the playing field. Two dead guys, for example, will always play to a draw. And as the evening wore on, it was Connors who seemed closer and closer to death. His talents were obviously still far superior to Lloyd’s, but his level of play dropped considerably after the first set, when he began having more and more trouble reaching Lloyd’s lobs and dinks.

Neither player seemed overly concerned about winning or losing. The linesmen were awful all match long, so bad that in his day Connors would have headbutted a few of them or at least walked off the court. Judging by Friday’s comportment, the latter-day Connors has realized the merits of sportsmanship. On more than one occasion, he asked the umpire to reverse a call and award a point to Lloyd. The spectators cheered him each time.

Even as the quality of the tennis deteriorated noticeably, people minded their manners, with one audible exception. Connors had just made a long but ultimately vain run after a nice Lloyd drop shot (an anachronism in itself). “You would’ve gotten that yesterday!” screamed someone from the cheaper (if not cheap) seats. Yesterday, back when tennis was such an easy game to play, Connors would have given the guy the finger, but the comment, painfully obvious as it was, hit home. Connors stopped and looked toward the grandstands, and as he stuttered through a jokey rebuttal, his feelings appeared genuinely hurt. Shortly after the heckling episode, it became clear that his wounds weren’t all emotional. A hip injury he’d suffered a few months ago flared up, and as the second set progressed, Connors began limping, grimacing, and muttering curse words after most points. A little more than an hour into the match, he slumped in a courtside chair and told the umpire he’d resigned. As the forfeit was announced, the crowd gave a smattering of applause, and even though a doubles match was scheduled for later that evening, most headed quietly toward the exits.

I went to Connors’ post-match press conference, an affair that had depressingly little in common with the one I attended in my youth. Connors wasn’t at all triumphant or jovial here. He wasn’t even upright. He took reporters’ questions while lying on his side in the women’s locker room at Woodmont, nude save for his shoes and the towel covering his balls. Tournament organizers banned photographers from the session. His comments included how he “had given it all,” how he would “always play no matter what,” how he “can only play one way” and would “always fight until there’s nothing left.” Despite the words, as I looked at Connors prone on his gurney, I just felt sorry for him, looking so old and mortal. And I felt sorrier for myself.

—Dave McKenna