DATELINE 6/9/2025

The Links at Outlook

Rain, rain go away, Pin High's got some golf to play. RANGE IS CLOSED!

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In an act of pure denial against the laws of weather, reason, and perhaps God Himself, the Pin High misfits packed up their hopes and rain gear and headed to Berwick, Maine—where summer is just winter with slightly greener frost. You could call it a search for greener pastures, but the only green we saw was envy for anyone smart enough to stay home. The rain didn’t fall. It attacked. It wasn’t cats and dogs. It was moose and bears. Mike Mackan, soaking like a bread bowl in chowder, was heard muttering, “I’m soaked to the bones... and that’s a lot of bones.” Medically accurate? Doubtful. Spiritually accurate? Absolutely.

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Yet in a twist so improbable it could only be credited to divine pity or dumb luck, the rain stopped at exactly 10:00 AM. So naturally, we teed off like it was a sunny day in Scottsdale, delusional and undeterred. And yes, somehow, golf occurred.

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The People Who Shouldn't Have Been There—But Were

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Mr. Hate himself, Jim Orsini, graced us with a second consecutive appearance. A streak! Apparently, Rick Keefe’s interrogation tactics worked. Orsini came dressed like he was guiding a fly fishing tour through Yellowstone—fly vest and all—just in case the water hazard on 11 had trout. He pulled another Irish exit, but did he really leave? Or has he transcended the space-time of our league entirely? No one knows. Schrodinger’s Orsini.

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For the first time in recorded golf league history, both Orsillos appeared in the same zip code. The Mafia family theory thickens. Was there a summit? A warning? A witness relocation ceremony? Not asking, they’re not telling. Fuggedaboutit.

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Meanwhile, Gibby Gilbert basked in home-field wetvantage. Having moved to Maine a decade ago—possibly to be closer to lobster or the Poland Spring—he’s driven a small continent’s worth of miles to these events. Now armed with another new BMW, he’s redefined both dedication and credit card interest.

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Match Play Madness: When Results Actually Happened

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• Moran v. Gibby: Moran treated Gibby like a wet noodle, 4&3. Gibby’s golf galoshes failed to activate.

• Ozzy v. Keefe: Keefe WD’d after hole #1, citing reasons that wouldn’t hold up in small claims court. Ozzy advances.

• Kimball v. Mackan: Kimball took down Mike, again proving he’s the best net player to never lose a stroke on his handicap. Sorcery? Maybe. Consistency? Definitely.
   

Now we look ahead:

• Ozzy vs. James W. Troup: Troup has declared a “trouncing.” We love the confidence. We hate the humility.

• Kimball awaits the victor: There’s a good chance Phil is already sipping a Gatorade in the final.

• Goody vs. Russ Moran: Bunkmates, tripmates, now enemies. Golf is cruel like that.

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Reynolds Watch: Still Missing

Jimmy Reynolds is still MIA. Rumor has it he’s joined a private club so exclusive it doesn’t allow him in. If seen, do not approach. He may be deep into a meditation session or a really long backswing

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And Then Came the Villa-bomination

The real story? Yours truly—Anthony “Birdie Machine” Villa—went nuclear on holes 16, 17, and 18. Three birdies. In a row. That’s not golf, that’s glitching the matrix.

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• On 16, a 25-footer snuck in like a thief in the night.

• On 17, a dart to 20 feet, a chip, a putt, and a whole lot of sadness from Troup, who bet against me and paid the price.

• On 18, 3-wood missile, a wedge to 15 feet, and the right-to-left breaker of Timmy's spirit—and Troup's DraftKings wallet.
   

Final score: +5, beating Kimball by one and earning this old dog his second win of the year. And yeah, I heard you muttering, “Must be nice.” It is.

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Next Week: The Ledges, the Legacy, and the Missing Men

As the league prepares to head back to Maine—where logic says not to go but tradition says otherwise—we return to one of Jay "where's my shoes" Gilbert’s favorite tracks: The Ledges. It’s a homecoming of sorts, soaked in both rain and reverence. Jay may have passed, but his spirit absolutely lives on every time we slice one into the woods and swear at a three-putt. Playing his course again means something—whether you admit it or not.

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That said, there will be two notable absences: Troup and Villa, who have taken their talents (and egos) to Oakmont for the U.S. Open. Not to play, relax—just to heckle from inside the ropes, overanalyze grass blades, betting the ponies while working and pretend they’re part of the broadcast team. Priorities, gentlemen.

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So good luck to the rest of you brave enough to face The Ledges. Just remember: Jay will be watching... and laughing... every time you chunk one into the drink.