Thursday, September 4, 2025

Cup Mania - Part I: Cypress Dreams

The serious golf is well behind us, but there are two September weekends that should be circled on your calendar, with the first upon us.  While Ryder Cup venues have been mostly dreary affairs, the USGA and R&A have hit it out of the park, having alit at Seminole and the Old Course in recent years, and this week might just be the best venue yet.  At least the most photogenic....

Your humble blogger has personal history at Cypress Point, having played it twice in the Mesozoic Era (OK, technically the 1980s), ironically before I was a sufficiently avid golfer to understand what a lucky bastard I was.  Is it as good as they say?  That's an easy one, as it's far better than even its elevated reputation.  I usually tell folks that it's not only the best course they will never play, it's actually the best three courses they'll never play, as it's a sublime mash-up of parkland, dune and ocean-front holes, leaving only that finishing hole to ignore.

I'll lede with this hole-by-hole video of the course narrated by Condoleezza Rice, which is well worth 10:57 of your time.  Don't worry, I'll wait for you to finish before I move on.


Cypress Point has its own unique place in the history of our game, though the game has largely moved on from it to the game's detriment.  Cypress was the most interesting of the three historic Crosby Clambake venues, the scene for this iconic moment involving Jack Lemmon, Clint Eastwood and Peter Jacobson:

Yeah, while we were micromanaging membership polices, the Tour replaced Cypress with Poppy Hills, a trade so one-sided I can only assume it was negotiated by Brian Cashman.

I'm going to lean heavily on Geoff here, but the history is pretty wild.  There's two aspects that I find most interesting, the first being that Saint Alister MacKenzie, who created one of the masterpieces of golf, was no better than second choice for the project.  Seth Raynor had the job but unfortunately passed away before his design made it past the planning stages.

The second fascinating occurrence is the confluence of Mackenzie, Bobby Jones and fate.  By way of background, Pebble Beach opened in 1919, but the original golf course was by all accounts a fairly unremarkable effort by two amateur designers.  Pebble's coming out party was the 1929 U.S. Amateur, before which Chandler Egan, a former Amateur Champion and silver-medalist at the 1904 Olympics, created what is now Pebble Beach, assisted behind the scenes by Alister Mackenzie (who had built Cypress Point and was finishing Pasatiempo further up the coast).

What I love most about history is its randomness, and in this case we have in spades.  Bobby Jones arrives for that 1929 Amateur at the height of his powers, you might remember that he had a pretty good 1930, but then golf intervened:

“It would’ve only been a natural connection for Bobby Jones to hire Donald Ross,” said Pinehurst historian Lee Pace.

When Jones went to Pebble Beach to compete in the 1929 U.S. Amateur, it was assumed that Ross would design Jones’ new course.

Fate intervened.

In the first round of match play, Jones faced the then-unheralded Johnny Goodman, a 19-year-old from Omaha, Nebraska. Goodman would go on to win the 1937 U.S. Amateur – and the 1933 U.S. Open, becoming the last amateur to do so – but it was his performance against Jones that would create a ripple effect throughout the game.

Goodman won the first three holes. Jones staged a furious rally, but Goodman hung on, 1 up.

Jones, presumed by many to make a deep run in the championship, had to wait several days before his scheduled return trip home. He spent his time on the Monterey Peninsula. He played Cypress Point, designed by Alister MacKenzie, then took part in an exhibition at nearby Pasatiempo, also designed by MacKenzie, who attended the event and talked with Jones throughout the round.

Somehow I've gotten this deed into things without mentioning Marion Hollins, who was the force behind Pasatiempo and Cypress.  There's a famous story that the architect said it was a shame that the carry to where the 16th green is was too daunting, and that Marion Hollins just dropped a golf ball and pulled off the shot, proving it playable.  What's interesting to me is that I had heard (assumed, perhaps) that the scene was with Mackenzie, although on a recent broadcast it was said that she hit that shot in front of Seth Raynor, not the Good Doctor.  One of those stories perhaps too good to fact check.... 

Geoff has a lot of Cypress coverage, beginning with this provocative post:

Spoiler alert, here's his sub-head:

No way.

Followed by this:


 Hate to argue with Geoff, but I'm not sure you could screw up a course on that piece of land....

Since this year’s Walker Cup host site opened in 1928, collective wisdom has insisted that any old schmuck with a handicap lower than 36, at least one eye, and magazine panelist business card could have taken Marion Hollins’ marching orders, accommodated financial backer Samuel Morse’s demands, worked from Seth Raynor’s first routing, and proceeded to design something comparable to what Alister MacKenzie, Robert Hunter, and The American Golf Course Construction Company pulled off at Cypress Point.

Not a chance.

A century removed from the 1925 to 1930s golf architectural gold rush that saw the art enjoy an incredible five-year burst of American designs inspired by National Golf Links and Pine Valley, masterworks like Cypress Point employed innovative techniques and design lessons learned to propel the art forward. This resulted in seemingly uber-natural works that “looked like they’ve been there forever,” but with a lot going on under the hood. By employing new tools and driven by a desire to do right by the canvases they were handed, several architects produced sophisticated designs capable of exciting golfers for generations.

I love his take on what followed this Golden Age:

The Great Depression put a sad and far-too-damaging halt to the guiding spirit of that robust
period. One that in California alone saw the creation of Cypress Point, a radical overhaul of Pebble Beach, Riviera, Bel-Air, and Pasatiempo. Even more remarkable? All were real estate developments.

When course construction resumed after World War II, the approach to financing, building, and designing courses within similar development schemes emphasized a mass-production, hard-is-good approach that protected land devoted to home sales. Those pesky details that affect golf shots or the overall experience became way less important. Armed with mass earthmoving tools, any craftsmanship or devotion to building a seemingly natural course full of intrigue gave way to a depressing uniformity.

Trent Jones to the rec courtesy phone.  That's collaborator Robert Hunter with the Good Doctor during construction at Cypress Point.

Geoff throws some shade to Raynor:

MacKenzie was at the center of these driving forces when the Cypress Point project received the necessary support to finally break ground. He brought a different personality to the job than his predecessor, Raynor, who had a portfolio of incredible works and big-name backers in Hollins and H.J. Whigham. But as a non-golfer engineer, Raynor’s best work amounted to the music equivalent of an ingenious cover artist. Raynor took the basics of “template” holes, taught to him by C.B. Macdonald, and regularly put new twists on those wherever he went. Raynor took difficult sites and made most of them (sorry, Lido) functional. But he was not an artist nor a salesman of MacKenzie’s ability. He could not have pulled off what MacKenzie’s team accomplished.

As a golf course site, Cypress Point had the usual site quirks related to soil, irrigation, and weather. Several holes required manufacturing that remains indecipherable today. Microclimates and differences in soil forced decisions about what kind of embellishments should be made to bring out the best features and to never do aesthetic battle with the dunes, cypress, pines, and ocean front holes.

That’s a fancy way of saying that Cypress Point did not need an architect to come in, play his Redan, Double Plateau, and close out the encore with a Biarritz. Nor would his deep, straight-lined, grass-faced bunkers have worked on a site of such unusual beauty.

In hindsight, we really can't know how Raynor's Cypress Point would have come off, w2e just know that Mackenzie's was, well 17 holes of perfection followed by an uphill walk back to the clubhouse.

Like a trusty group of session players who can play anything or improvise when called upon, the American Golf Course Construction crew could adapt to the inevitable hiccups and last-minute pivots of a golf course construction project. The Cypress job involved big personalities, but at least they were looking to build the best holes possible while also protecting real estate and tourism interests. Marion Hollins was there to guide the overall project as a visionary golfer who also could welcome A-list visitors, push the artisans, and inspire confidence in potential members or lot buyers.

Cypress Point’s finished course featured a highly unorthodox routing. Before various design norms like par 72, returning nines, and other mysterious rules led to so many forgettable courses, this one violated every unwritten edict. Not many of the holes penciled in by Raynor made the final cut, nor should that matter. The West Coast Chapter of the Seth Raynor Marching and Chowder Society might disagree.*

That's the last 'graph before the paywall, so it's a hanging asterisk.  I excerpted it because of the routing comment, Cypress featuring for member play both back-to-back Par-5's, as well as back-to-back Par-3's (at least for member play).  

Geoff has lots of additional coverage, here focusing on the Par-5's:

The par-3s are deservedly famous, but the par-5s are as great as any in the world. A look at three front nine holes that bend left and violate design rules in all the best ways imaginable.

 I'm listening:

Cypress Point features a trio of par-5s in a five-hole stretch. On a normal, non-Walker Cup day, there are four “three-shotters” in its first 10 holes.

Another twist: the fun comes early in the round. The second, fifth and sixth holes are all par-5s and each bends to the left.

Cue up the panelist points deduction for a distinct and concerning lack of shot value balance!

On a course full of design abnormalities, no rule-bender better encapsulates why every other plaid-clad, blueprint-ferrying, finger-pointing genius is only vying for a distant second in the Grade I Greatest Golf Architect Stakes.

The outside world is unlikely to see much of the action on Cypress Point’s first three par-5s during this week’s Walker Cup. Not to worry. You won’t miss seeing how the architect ingeniously designed them to play. The fifth (and tenth) have been reduced to par-4s on the Walker Cup scorecard—as if it matters in match play. Maybe the USGA setup team did this so historians will someday ask, “who let the equipment get so juiced that we drag the masterworks down to the crass level of worrying about one corporation’s bottom line and their VP’s second-home purchasing power, above the game?” Or something like that.

If you’re coming to the Walker Cup, shut out the silly approach distances and pay special attention to the front nine’s par-5s while imagining how they play for mere mortals. There are design lessons to be learned!

 Those TV windows are a real problem.

I think Geoff is onto something here:

As with the other par-5s at Cypress Point, it’s MacKenzie’s focus on the lay-up shot that makes the second holes so lively and timeless. Like his hickory-era counterparts George Thomas and A.W. Tillinghast, certain architects built surprisingly long holes but finished them off with lightly protected greens. This prompted them to put more thought and decision-making into the second shots of par-5s, whereas today’s design focuses largely on the shot going for a green in two.

I would only add that I think Pete Dye refocused the world on creating interesting lay-ups, after the misery of the Trent Jones era.

Geoff isn't afraid to stake out bold positions:

The often-criticized finishing hole could play a pivotal role in the 50th Walker Cup.

Ok, Geoff, but the case seems to rest on matches being decided before reaching this hole:

An average of 9.5 matches have reached the 18th hole in the last six U.S. Walker Cups. Only six
contests came to Ocean Forest’s closer, while a whopping 13 of 26 matches made it to Seminole’s finishing hole four years ago.

During the 1981 Walker Cup matches at Cypress Point, eight of 24 matches reached a home hole that famously prompted Jimmy Demaret to label this year’s venue “the best 17-hole course in the world.”

There are hundreds of more impressive finishing holes than Cypress Point’s. It’s never helped by sitting just down the 17-Mile Drive from one of the very best at Pebble Beach. Other nearby closers at Monterey Peninsula CC’s Shore and Dunes, Spyglass Hill, Spanish Bay, and Pacific Grove are generally forgettable for similar reasons to Cypress Point: the architects needed to return golfers from the ocean-adjacent holes and back to clubhouses situated on higher ground.

But is the last hole for this year’s matches really as terrible as Demaret and plenty of others have implied? Or maybe just a letdown after the extraordinary journey that leads up to it?

Maybe there's a better case made behind the paywall?

Cypress Point’s 18th hole also receives harsher reviews than its neighbors because the rest of the course offers so much drama, jaw-dropping beauty, and thrilling shots to play. No other hole at CPC is as narrow or forces a layup off the tee. And the apathy toward No. 18 also prompts a question: does a finishing hole have to be a rousing, knockdown, drag-out extravaganza of thrills and spills to receive declarations of greatness?

Not every great symphony, concerto, pop album, or story ends with a bang. A good sandwich peaks early before reaching the crust where you’re missing those initial bites. Same goes for a muffin. It’s pretty much all downhill after the top half.

In traditional storytelling structures, the second act’s conclusion is where stuff goes down before the ending provides (sometimes) a satisfying resolution. And it’s not like Cypress Point’s 18th offers a peaceful and gentle fade to black. Two very good shots are required, even if you aren’t entirely sure how to get there.

Part of the problem lies in what comes immediately before the 18th. Golfers are coming off the world-famous 375-yard 17th, even though it's got its share of awkward qualities, thanks to the cypress in the way of most average golfers’ tee shots. That will not be an issue for the Walker Cuppers, who will power drives past them thanks to their relentless high-intensity interval training.

After the beauty of No. 17, Cypress Point’s home hole plays through a narrow thicket of old Monterey cypress. Some are now mere twisted trunks, prompting Lewis A. Lapham, the son of club founding member Roger who hit shots during construction for MacKenzie, to write how the cypress looked “like an alfresco exhibition of modern sculpture.”

Draw your own conclusions from the video at the top of the post, but the tee shot is as awkward as anything I've ever experienced on a golf course.   

I think Geoff is on far more solid ground in discussing Cypress Point's most famous hole:

The most incredible one-shotter in golf will get a rare public showing during next week's Walker Cup. Its architect often sounded skeptical about Cypress Point's 16th working as a long par-3.

Do tell:

Alister MacKenzie never shied away from a hearty humblebrag. And the master architect was also no fan of losing golf balls to bodies of water.

At a time when hickories were still the stick of choice and balls were made of Malaysian tree gum, the vast majority of golfers couldn’t carry the ball 200 yards, leaving MacKenzie conflicted over what became a career-defining creation— Cypress Point’s par-3 16th—that most golfers would sacrifice a limb to tackle just once.

“Being a Scotsman, I am naturally opposed to undiluted water,” the designer of Cypress Point wrote. “The admixture of water with both highballs and hazards is an art depending to a great extent on the right time and the right place. My Scotch blood comes to the fore again in prejudicing me against any hazards which create the expense, annoyance and irritation of losing balls or even searching for them.”

When MacKenzie and Robert Hunter took over the Cypress Point design job following the passing of Seth Raynor, the decision had been inadvertently made to make the 16th hole a par-3 instead of a par-4.

The boss had made her feelings known.
Postcard with Alister MacKenzie on the tee (left), postcard of Cypress Point before golf (upper) and MacKenzie, Marion Hollins, H.J. Whigham and Robert Hunter during construction. (lower right)

What a thing!  To have built this golf hole when players were still sporting hickories is quite unbelievable.

“To give honor where it is due, I must say that, except for minor details in construction, I was in
no way responsible for the hole,” MacKenzie wrote. “It was largely due to the vision of Miss Marion Hollins [the driving force behind Cypress Point]. It was suggested to her by the late Seth Raynor that it was a pity the carry over the ocean was too long to enable a hole to be designed on this particular site. Miss Hollins said she did not think it was an impossible carry. She then teed up a ball and drove to the middle of the site for the suggested green.”

Long before cars and golf came along, the 16th hole site had become a tourist destination featured on postcards and visited by horse-drawn wagons. Taking away the destination for a private club meant the architects needed to get it right. Envisioning golf holes on the spot known as “Cypress Point” required little imagination. The former 17-Mile dirt path was dotted with grasslands and wildflowers just waiting to be converted to fairways. The real trick would be in finding the sweet spot for a tee.

In playing the hole way back when, I just hauled off and tried to cover the carry.  Amusingly, my first attempt almost made it, settling in the ice plants short of the green, but each subsequent effort came up shorter.  With a scorecard in your pocket you'd almost have top play out to the left towards that solitary tree, which felt quite awkward.

In a later post, Geoff gives us one of his characteristic by the numbers bits:

    • 1928: Opened for play
    • 2: Architects of record (Alister MacKenzie and Robert Hunter)
    • 2: Consulting architects since 2014 (Bill Coore and Ben Crenshaw)
    • 70: Par for the Walker Cup (36-34)
    • 72: Par at Cypress Point (37-35)
    • 6,620: Walker Cup yardage (3,409-3,211)
    • 73.1/141: Course rating and Slope
    • 0: Sprinkler heads with yardages to the green
    • 63: Course record by Ben Hogan, Jim Langley, Adam Scott, Casey Reamer, Kramer Hickok
    • 3: Par-5s in the first six holes (non-Walker Cup pars)
    • 137: Yardage of the shortest hole (No. 15)
    • 579: Yardage of the longest hole (No. 2)
    • 141: Feet above sea level, highest property point (5th green)
    • 23: Feet above sea level, lowest property point (14th fairway)
    • 4,500: Average green square footage
    • 157: Total property acres
    • 32: Acres of fairway
    • 30: Acres of rough
    • 104: Bunkers
    • 3: Holes with the Pacific Ocean in play (15-17)
There's lots of other good stuff in the post, but I especially like that Geoff focused on this:

Match Play Moments

The fifth and tenth are listed as par-4s but will be the only two of the 10 par-4’s like to see more than a wedge for an approach shot. Modern distance absurdity could give birth to some fascinating match-play moments if players are feeling frisky (or desperate).

9th - This one has been drivable since MacKenzie and Hunter figured out how to nestle a green into the dune. But now that it’s essentially a long par-3, there could be scenarios where the outcome of the tee shot by the player holding the honor could lead to—gasp!—a lay-up. The right side provides a much better angle into any hole location.


Just a great hole through the dunes.

  • 14th - This 391-yard dogleg right generally calls for an automatic layup and this should be the case again. The risk of taking on the dogleg involves a lost ball or unplayable lie in the cypress that surrounds the second half of the hole. But in match play featuring a bunch of young golfers who need a bold shot to get back in a match? It’ll take a drive carrying 315 yards but will leave a flip sand wedge and much better view of the tiered green compared to what lay-ups will see. It’s 360 to the front of the green. But is the direct line worth the risk?
  • 17th - Perplexity has always dominated the thought process on this 381-yarder thanks to a cluster of Monterey cypress in the fairway. The maimed but still standing giants stand where most golfers would like to hit their best drive. Downwind and with firm fairways, players may try to blow past the trouble to set up a flip wedge shot into a pretty quiet green. Weather, the state of a match, the less imposing condition of the cypress could all factor into the drama. Smart golfers are most likely to still lay-up now that modern launch angles and the less-imposing cypress only obstruct views instead of shots.
Sure, though I'm wondering how the lads will handle No. 16.  We expect them to go for everything but, while they can readily reach it, any dispersion will end up wet.  Also remember that the Walker Cup does not include fourball, so only one ball in play each hole.  If the player with the honor goes for and misses the green, doesn't his opponent lay up?

I hope I've whet your whistle and that you'll tune in to see one of the truly special places in golf.  Not that watching is all the easy, as here are your TV windows:

Where to watch Walker Cup 2025

Saturday, Sept. 6: 12:30 p.m.-3:30 p.m. (Foursomes), Peacock

Saturday, Sept. 6: 7 p.m.-10 p.m. (Singles), Golf Channel

Sunday, Sept. 7: 12:30-3:30 p.m. (Foursomes), Peacock

Sunday, Sept. 7: 7 p.m.-10 p.m. (Singles), Golf Channel

Set your DVR.  I expect to be signing up for Peacock, only to cancel immediately.  

Enjoy the Walker Cup and Cypress Point, and then next week we can circle back and pick up our Ryder Cup blogging.  Have a great weekend. 

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