The Chubb Classic at 39: Why Naples’ Senior Tour Anchor Still Matters

Look, I’ve been covering professional golf since the ’90s, and I’ve watched the PGA Tour Champions circuit evolve from a genteel retirement party into something genuinely compelling. The Chubb Classic—returning this week to Tiburón Golf Club for its sixth consecutive year—is a perfect case study in why these senior events have become essential to understanding modern golf.

What strikes me most about the Chubb’s longevity isn’t just the tournament’s staying power. It’s what the tournament represents: a community that has figured out how to keep elite professional golf relevant across generations. Not every city can say that.

The Stability Story Nobody’s Talking About

In my three decades around the tour, I’ve watched tournaments come and go with the regularity of snowbirds. Sponsors get cold feet. Venues change. Cities lose interest. But the Chubb—which began as the Aetna Challenge in 1988—has endured. That’s 39 years of consistent professional golf in Southwest Florida. The fact that it’s “the longest-running PGA Tour Champions event in the same metro area” isn’t just trivia. It’s a testament to something deeper: a community that values golf enough to keep showing up.

Having caddied for Tom Lehman back in the day, I watched him transition into the Champions Tour. And I can tell you—the Champions Tour isn’t where players go to fade away. It’s where they prove something new. These aren’t exhibition matches. These are competitors who’ve forgotten more about golf than most of us will ever know.

Leonard’s Repeat Bid Signals Real Competitive Heat

Justin Leonard’s defending his title this week after what can only be described as a statement victory last year. Consider this: Leonard finished 15-under and won by four strokes—that’s dominant golf by any measure, especially among players in their 50s. The fact that he’s a 12-time PGA Tour winner, including an Open Championship and Players Championship, tells you something about the caliber of competition the Chubb attracts.

“Justin Leonard earned his first PGA Champions Tour victory at last year’s Chubb, birding five of the final seven holes to finish 15-under and win by four strokes over Billy Andrade.”

That closing stretch—five birdies in seven holes—is the kind of finish you see from players who still have something to prove. Leonard’s not here for nostalgia. He’s here to win. And that competitive fire is what separates the Chubb from a typical senior event.

The Field Tells the Real Story

Walk through the 2026 field and you’re looking at a who’s who of golf royalty. Bernhard Langer—five times a champion here—is proof that mastery transcends age. David Duval and Tom Lehman, both former World No. 1 players, are competing seriously. Ernie Els, Chris DiMarco, Rocco Mediate… these aren’t has-beens. These are titans of the game.

What I find particularly fascinating is the breadth of eras represented. You’ve got players from the pre-internet 1980s competing alongside guys who dominated the early 2000s. That kind of competitive timeline—spanning four decades of professional golf—creates something special. It’s not just golf; it’s continuity.

The Local Angle That Matters

George McNeill, a 1993 North Fort Myers High School graduate making his Champions Tour debut, represents something I’ve always believed in: golf’s ability to create legacies within communities. McNeill’s got 300-plus PGA Tour starts under his belt, with 21 top-10 finishes and two victories. He’s earned his spot. But more importantly, his presence reminds us that tournaments aren’t just about who wins—they’re about what they mean to the people watching.

That local connection drives attendance. That’s why parking gets organized at the First Baptist Church. That’s why there’s a complimentary shuttle. That’s why the SERVPRO Hero Outpost provides free admission and food for military, police, fire, and EMS personnel. These details matter because they show a tournament that understands its community obligations.

The Sustainability Question

Here’s what concerns me slightly, and I’ll be honest about it: the PGA Tour Champions circuit is stronger than ever, but it’s also facing pressure from LIV Golf’s ambitions and the PGA Tour’s own restructuring. The Chubb isn’t facing existential crisis—Chubb Corporation’s sponsorship is solid, and the venue is locked in through at least another cycle. But the landscape is shifting.

What keeps the Chubb secure, I think, is precisely what the article highlights: charitable commitment. The tournament has supported more than 30 local organizations since 1988. That’s not marketing spin—that’s real community infrastructure. When a tournament becomes part of the civic fabric, it becomes harder to dislodge.

“A portion of the ticket proceeds will be donated to local charities throughout Southwest Florida. The Chubb Classic has proudly supported more than 30 charitable organizations since its inception in 1988.”

Why This Matters Beyond Naples

The Chubb Classic is a model for how professional golf can thrive at the regional level when executed with intention. It’s not trying to be Augusta. It’s not chasing the glamour of majors. It’s being what it is: a well-run, community-invested professional golf tournament where elite competitors still play for meaningful purses.

The broadcast window (Golf Channel, Friday 11am-2pm, Saturday-Sunday 3-5pm) ensures accessibility. The ticket pricing ($20-$50 for daily grounds) keeps it affordable. The veteran appreciation program recognizes who’s often filling those galleries. These aren’t accidents. They’re the decisions of an organization that understands its mission.

After 35 years covering this tour, I’ve learned that golf’s future isn’t determined by the biggest names or the flashiest venues. It’s determined by tournaments that show up year after year, build community, and never lose sight of why golf matters in the first place. The Chubb gets that. And in 2026, as it has for 39 years, it’ll prove why it belongs.