The Second Legend of Sleepy Hollow: Hagestad wins third US Mid-Amateur
Amateur Golf

The Second Legend of Sleepy Hollow: Hagestad wins third US Mid-Amateur


---by Washington Flemma, Special to Golf News Net and
Found among the papers of Mr. Ryan Deidricht Knickerbocker---

SLEEPY HOLLOW, N.Y. – Nestled in the bosom of a spacious cove on the eastern shore of the Hudson at an expanse of the river called the Tappan Zee by the Dutch, but more recently stylized by one Italian as “Mario M. Cuomo Bridge,” where they prudently reduce speed to 45 miles per hour and implore the protection of Batman, there lies a market village known as Tarry Town, so named for the propensity of working gentlemen to tarry in the bars on payday and come home empty-handed to angry housewives brandishing rolling pins.

The next two weeks would be living hell for them.

Yet far more frightful than furious spouses are the myriad ghosts, ghouls, goblins, phantoms, phantasms, spectres, poltergeists, Beelzebubs, Saurons and various other Voldemorts that haunt the region high above the river banks, across from the frowning brow of the Palisades – a forested hamlet called Sleepy Hollow. A drowsy, dreamy influence seems to hang over that land and pervade its very atmosphere. Some say that the place was bewitched by a high German doctor during the early days of the settlement; others, that an old Indian chief, the prophet or wizard of his tribe, held his supernatural rituals there. And still others say that the Riddler tried to open a wormhole in space and time to another dimension and let loose some other DC Comics uber-villain.

Get our content ad-free by becoming a GNN member for $2/month!

Whatever the origin, certainly the place still continues under the sway of some bewitching power; the whole neighborhood abounds with local tales, haunted spots, and twilight superstitions and nightmares.

The dominant spirit, however, that haunts this enchanted region and seems to be commander-in-chief of all the powers of the air, the wind, the trees, the rocks, and all the minions of Hell itself is the supernatural manifestation of a golfer that haunts the holes of the Vanderbilt–Astor–Rockefeller estate: the Hagless Horseman.

“Wait,” you say. “Don’t you mean the Headless Horseman?”

No, I don’t. He’s a whole different guy altogether.

The Hagless Horseman is the terrifying alter ego of a champion amateur golfer named Stewart Hagestad. Stewart is one of the most decorated amateur players pf this or any generation. He’s won United States Golf Association events around the country, played internationally on USA teams and even was low amateur of the Masters one year. He needs a forklift as all of his trophies weigh a ton and a half. Better still, he carries the mantle of golf’s virtue as well as any amateur has in over a century, and that includes Bobby Jones and Jay Sigel.

But then came Sleepy Hollow.

Sleepy Hollow entranced him, snared him, possessed him, and he in turn succumbed to its enchantments:

  • Over 100 years of history;
  • Its membership an index of American elite society;
  • Designed by the greatest golf architect of that or perhaps any age, Charles Blair Macdonald;
  • The course an amalgam of the most strategic golf holes from around the world;
  • Every single shot on the course riding the razor’s edge of success or failure;
  • A majestic setting along the river so gorgeous it would earn the envy of every Italian master of the Renaissance Age.

Tell it true: Would you be able to resist Sleepy’s siren song? None who live can.

So, when the USGA brought the 42nd Mid-Amateur golf championship to Sleepy Hollow Country Club, they unknowingly set loose upon the field their ultimate doom. You had to sense it was coming – the Golf Gods know when to throw thunderbolts with both hands.

And so it was that on a day when the Golf Gods sparred with lightning and rain slashed across Sleepy Hollow Country Club that one Stewart Hagestad went into those woods and vanished and returned as the Horseman; transmogrified into all the fury and vengeance of the sporting gods, dispensing opponents completely and mercilessly before vanishing again into the mists of time and history like a reverie.

Kinda like “Night Rider” meets “Punisher,” but I digress.

Now ever and anon the Horseman is seen by the country folk hurrying along in the gloom of night, as if on the wings of the wind. His haunts are not confined to the valley, but extend at times to the adjacent roads, and especially to the vicinity of a certain haunted bridge. That’s at the crossover between holes three and 16.

Yet still, the tournament attracted suitors from all across the globe – 20 different countries and 42 different states – and, one by one, they fell in love with her blaze of golden sunlight, the purity of all she represented.

Golfers have foolish hearts toward trophies. And this particular trophy -- plump as a partridge; ripe and silver-cheeked as a morning of pale spring still clinging to winter’s chill -- was universally famed, not merely for its beauty but its vast symbolism. But to the hungry golfers, she was a little coquette.

How the players’ mouths watered as they looked upon this sumptuous promise of luxurious fare. In their devouring minds’ eyes, they pictured to themselves victory, glory, and accolades. Their hearts were buoyant as 263 of them set forth, knights-errant all. Oh, those poor Ichabods! For those who do not learn from literature are destined to repeat it.

And day after day, player by player, round after round, the news slowly spread. There is something here with us:  the Horseman rides…and tonight he comes for you!

Suddenly upon putting a golf tee in the ground on the first hole, players unleashed all the terrors of the night, all the phantoms of the mind that walk in darkness, preying upon the fear in your heart, every spectre besetting upon you in diverse shapes.

It’s a lonely perambulation around the course, an almost fatalistic waiting. When will the birds stop chirping? When will the stillness fall with deafening silence as though the world stropped breathing? And then what will you do when you finally hear the hooves pounding, the neighing of the giant steed, the gleam of the steel as it cuts like a scythe through the air.

One by one, the Horseman pursued them on their walk homeward, feeding off their terror, a will-o-the-wisp luring them one by one to the killing bottle, but toying with them first. Here and there sending fearful shapes and shadows on their path. Then more dim and ghastly glares of night as the last trembling rays of light faded, shrouding them in gloom…and impending doom.

How often did they shrink with fear? How deeply did their blood curdle at the sound of the wailing wind as though the Horseman’s voice cried out to them with the maniac cackle of some rubber-suited Scooby-Doo villain? How they feared to look over their shoulder, lest they should behold him tramping close behind.

Then it came. The rushing blast, wind howling among the trees, and the galloping Hagestad on his daily scourings!

The Blair Witch ain’t got nothin’ on the Horseman.

As they hear his approach – unstoppable, unconquerable – all the stories of ghosts and goblins that they had heard in the afternoon now came crowding upon their recollection. The day grew darker and darker; the sun seemed to sink deeper in the sky, and driving clouds hiding it from the sight. Evern the trees seemed to do his bidding, crowding closer, the intense claustrophobia cloying, choking you until finally you see him.

Silhouetted against the sky like the flag at the fifth green, dark and forbidding, you see him, towering like a giant, clubs gleaming like scimitars.

Then the flaming pumpkin slams you in the face.

One by one, the last of the players fell beneath the steely slash of the Horseman’s Taylor Made forged irons – forged in Hell or forged in the crucible of match play golf? I’m afraid this time it’s both.

The Hagless Horseman took the trophy and the medal and vanished, leaving many gallant but disappointed suitors in his wake, all feeling the gnawing loneliness of bitter defeat.

As for the future, Hagestad will return to Newport Beach, but we will see him for many years to come in golf, always at the vanguard of the amateur game, perhaps its greatest living ambassador. But the Horseman will return too – Hagestad’s steely nerve and iron will on the golf course. The Horseman never left Hagestad; its touch will always be there. And anyone who does battle with him will have the touch of the Horseman to contend with.

But for those of you who l might venture to Sleepy Hollow, heed this advice:  The Horseman is still there. He’ll always be there. And anyone who wishes to summon him to do their golf bidding need only journey deep into those woods, stand upon the haunted bridge, and utter this incantation:

Chief among the cursed souls that in that valley dwell,
A phantasm malevolent, most terrible and fell,
The Hagless Horseman is the woods’ most terrifying shade,
All those he beckons to are doomed to helplessly obey,
And to the Champion’s Graveyard this unconquerable king,
Our greatest heroes in defeat inexorably brings.
Patrolling bitter watches of the night their frightful end,
Until the Horseman rides once more and haunts us yet again…

About the author

Jay Flemma

Jay Flemma

Starting with a blog and a dream, Jay Flemma launched his first sports-writing website in 2004. Some 13 years and 25 major golf championships later, Jay has won multiple national sports writing awards. Besides GNN, his work has appeared in numerous books as well as on-line at Cybergolf,, GolfObserver, and many other sites and print magazines. When not trying to find a lost golf ball, Jay is an entertainment, copyright, Internet, sports and trademark lawyer in Manhattan. His clients have been nominated for Grammy and Emmy awards, won a Sundance Film Festival Best Director award, performed on stage and screen, and designed pop art for museums and collectors. Jay lives in Forest Hills, N.Y., and is fiercely loyal to his alma maters, Deerfield Academy in Massachusetts and Trinity College in Connecticut.