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  • Writer's pictureMason Reed

#34 Cypress Point (Top 100 rank #2)

May 2024

One of the (many) weird things about this project is playing golf courses out of order. I guess in a perfect world you would start at number 100 and work your way to number 1. But that's not how it works and you play what you can play, when the opportunities arise. This was the case with Cypress, which many respected people claim is the best course in the United States. It's easy to see why that's the case - it has lore, ocean holes, remarkable views, an iconic course designer and very high prestige.

A friend of mine at work told me he knew a member and asked if I wanted to play. I couldn't believe it. This was three months in the works. I had the opportunity to bring one person and Matt Cannan joined me along with two people I work with. An "unaccompanied" foursome (no members with us). Matt and I have become very good friends in a short period thanks to - wait for it - golf. Around 2020 two Chicago friends - Matt Andresen and Ryan Van Pelt - were making plans to move to Austin, Texas where I live. They were looking for a golf club to join and were checking out Spanish Oaks where I play golf. They were placed in a group with a couple of my friends on a random weekday. I had to work and joined my friends mid-round and met Matt and Ryan on the golf course. It seems like golf uniquely creates friendships among like-minded people and Matt, Ryan and I hit it off immediately. I would guesstimate that we've been on more than a dozen golf trips together in the 3-4 years we've known each other. Beyond golf they've become close friends that I rely on for all kinds of personal and career advice. They are the kind of friends that would remain friends even if we all stopped playing golf. That said, golf is a very useful framework for catalyzing our interactions. Matt and Ryan had a similar group of close friends in Chicago and one of the magical things they did was merge together their Chicago friends with their new Austin friends. We've all become close and Matt Cannan and I became friends through that fusion of friend groups. Matt Cannan would reach out to me as I was going through some personal challenges and check to see that I was doing ok. Matt and I would share book recommendations and have the conversations about life/happiness/feelings that sometimes men struggle to have because they seem "soft." So it was easy for me to use my precious +1 spot to invite Matt C. as I knew he had played a ton of famous courses but not Cypress.

We ate an early dinner at a dive restaurant. One bottle of wine for three of us - mild by our standards. Matt and I rolled into our hotel (which felt more like a hostel) around midnight and slept for 5 hours or so. We got up at dawn, grabbed coffee in Carmel and hit some warm-up shots at the Pebble Beach driving range (which you aren't allowed to do but we sweet talked our way into it). Around 8a we arrived at Cypress and the magic began.

Like other courses with strong reputations, I arrived with perceptions of Cypress that turned out to be untrue. I thought the reception would be cold and the general feeling would be "you're welcome" for allowing me to play there. Couldn't have been farther from the truth. Our car pulled into the parking lot, immediately adjacent to the first tee and immediately a caddie walked out and complimented our rental car (ha!) and welcomed us. The locker room staff was lovely, the pro shop welcome was as gracious as you have ever met and all of the caddies were happy for us to be there. Off to a good start before hitting a single tee shot. On the tee box, our caddies told us we could hit a breakfast ball (a second shot in case the first one stinks) and that we could take pictures anywhere you wanted. Both of these things are largely frowned upon at classy golf courses. My favorite takeaway from this experience - beyond the magic of the course - was how incredibly confident the club must be to welcome guests and treat them to a top-notch experience. Many (most?) highly ranked courses treat their guests like they are lucky to be there and/or they make them walk on eggshells. I was really impressed that Cypress does the opposite; they made me feel like a rock star.

The course itself deserves it's reputation. The water holes speak for themselves but the inland holes are fantastic too. Holes 5 through 9 in particular stand out as as good of a stretch of golf you'll find anywhere.

I don't know if I'll ever make it back to Cypress; I treat these experiences as if it's the first and last time I'll ever play. That forces me to appreciate the experience even more and soak up every moment. I love the Monterey Peninsula though, so I do hope I tee it up at Cypress again - where I know I'll be treated like a star.


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