Author: James “Jimmy” Caldwell

Chris Gotterup’s Masters Bet With Himself: Why Self-Belief Matters More Than Ever I’ve spent 35 years around this game, caddied for Tom Lehman, and watched enough young talents flame out to know when someone’s got the right mental architecture to stick around. Chris Gotterup has it. And what strikes me most about his approach to Augusta National isn’t just that he’s arriving as a two-time PGA Tour winner this season—it’s the principle underlying his decision to get there. He turned down Masters invitations before he’d qualified as a player. Let that sit for a minute. The Psychology of a Champion-in-Waiting…

Pebble Beach 2026: When Power, Celebrity, and Golf Collide—And Why That’s Actually Good for the Game Look, I’ve been covering professional golf for 35 years. I’ve caddied for major champions, watched the Tour evolve through boom and bust cycles, and I’ve learned that when a pro-am field reads like a guest list for a billionaire’s wedding, something interesting is happening in the sport—for better or worse. The 2026 AT&T Pebble Beach Pro-Am is shaping up to be exactly that kind of event. And after spending a few days analyzing the roster, I think what we’re seeing here is less about…

Chris Gotterup’s Meteoric Rise Signals a Tour in Flux—and It’s Refreshing In 35 years of covering professional golf, I’ve learned that the most interesting stories aren’t always about the guys winning majors. Sometimes they’re about the players who seem to come from nowhere, catch fire, and force you to completely reassess what you thought you knew about the modern game. Chris Gotterup is one of those players. Now ranked fifth in the world after his back-to-back victories to start 2026—including last week’s playoff win over Hideki Matsuyama at the WM Phoenix Open—the 26-year-old Jersey native represents something I haven’t seen…

Pebble Beach 2026: Why McIlroy’s Season Debut Matters More Than His Odds Suggest There’s something poetic about Rory McIlroy returning to Pebble Beach as the signature event opens the 2026 PGA Tour season. I’ve covered enough opening tournaments over 35 years to know that how a superstar begins their calendar year often sets the tone for everything that follows. And right now, watching the model project McIlroy to miss the outright win despite his impressive 2025 season tells me something interesting is happening on the PGA Tour landscape—the competition at the elite level has genuinely intensified. Let me unpack what…

In my thirty-five years covering professional golf—and I mean really covering it, from the dusty ranges of Q-School to the manicured fairways of Augusta—I’ve learned that the most telling moments aren’t always the ones that fit neatly into our scorecards or highlight reels. Bryson DeChambeau’s topped drive at LIV Golf Adelaide this week is one of those moments. On the surface, it’s absurd. Comedic, even. A ball that travels 245 yards after being struck just a foot from the tee box, somehow finding its way to a birdie on a par 5? That’s the kind of golf story you tell…

Cameron Smith’s Adelaide Declaration: What LIV Golf’s Confidence Really Means for Professional Golf In my 35 years covering professional golf—including a stretch as Tom Lehman’s caddie back in the ’90s—I’ve learned to listen carefully when major champions speak with conviction about the sport’s future. So when Cameron Smith tells you he’s confident LIV Golf will be thriving two decades from now, it’s worth paying attention. Not because he’s necessarily a fortune teller, but because his confidence reflects something real happening beneath the surface of professional golf’s ongoing restructuring. Smith made those remarks ahead of the LIV Adelaide tournament at The…

LIV Golf Adelaide: The Tournament That Found Its Audience (And Then Some) I’ve been covering professional golf for 35 years, and I’ve learned that the most telling indicator of a tournament’s viability isn’t what the suits in the boardroom say—it’s what the fans do with their wallets and their time. By that measure, LIV Golf Adelaide has done something remarkable: it’s become genuinely unmissable in a market that was starved for elite golf. When LIV Golf first touched down in Adelaide in April 2023, there was legitimate curiosity but also understandable skepticism. Australia had hosted majors and big tournaments before,…

McIlroy’s Pebble Beach Return: Why This Signature Event Matters More Than You Think After 35 years covering professional golf—and having spent a few seasons watching the tour grind from inside a caddie’s bib—I can tell you that certain tournaments carry weight beyond their purse size and television ratings. The AT&T Pebble Beach Pro-Am that kicks off this week is one of them, particularly with Rory McIlroy returning as the defending champion. On the surface, this looks like a straightforward story: the world’s No. 2 player is back to defend his 2025 title. But what strikes me about McIlroy’s arrival at…