A Surreal Week at Pebble

I came to the tournament expecting the most memorable thing about the week to be the courses. Instead, it was our group. Rounding out our foursome for the opening three rounds: one of golf’s great entertainers and professionals, Peter Jacobsen, and Billboard-topping musician Ben Rector. Caddying for Peter was the most recognizable and legendary caddie in the game, Mike “Fluff” Cowan. The week at Pebble would be Peter’s final professional tournament; he was retiring at the event that launched his professional career in 1975. In many ways, things were coming full circle. 

Ryan French, my closest friend and Monday Q Info founder, carried by bag for the week. “This place feels like a simulation,” Ryan said after our practice round at Pebble Beach.

There were three courses to learn then: Pebble, Spyglass Hill and Monterey Peninsula. Learning one course in a week can be a tall order, especially when you’ve never played it. Learning three courses is nearly impossible. Places on each course were left entirely unexplored and uncharted, requiring improvisation if my ball ended up there. 

One thing was for sure: missing on the wrong side of a hole meant you were dead. This was especially true at Pebble Beach, where angles are everything. Success requires embracing the dramatic cliffs of the Pacific and picking lines that seem dangerously close to trouble. I never was able to fully commit to some of them.

Monday of tournament week was a pro-am for the Boys and Girls Club of Monterey. When I arrived at Monterey Peninsula, I had forgotten the tour pays pros $3,000 for these outings. It was the most pleasant of surprises, and riding high on the newfound knowledge of being given a month and a half of rent payments, I donated half of the $3k back to the day’s cause. 

Tuesday was the big practice day: Pebble Beach with Dylan Wu, Nick Hardy and Jim Knous, followed by the pairings party. Ryan and I were giddy walking from the range to the first tee. Even seasoned pros pull out their phones for selfies on 7 and 18. We kept asking the same question in different ways: How did we get here?

Surreal.

Then came the prank. As with any good prank, gently poking one’s deeply held fear is a great premise. One of Ryan’s great concerns was his social media habits landing him in hot water. 

As we reached the first tee at Pebble, Anthony Gallino — who ran the caddie service — approached and informed Ryan he had violated Monterey Peninsula’s social media policy. Members were demanding his credential be revoked. Tournament director Steve John was in on it and reinforced the message. Cameras captured Ryan’s disbelief.

“I want you to find a new caddie and win the tournament,” he told me, saintly and near tears.

While I was only playing along to promote the tournament, my mom and wife later said it was cruel. Ryan handled it with grace. I waited for retaliation. None came.

We savored every step, every hole, every swing. The place left us in awe.

Our group teed off Thursday on the back nine at Spyglass Hill. Ben’s opening drive lodged in the base of a tree. My second shot at the par-5 11th, our second hole of the morning, plugged under the lip of a bunker 40 yards from the green. My three playing partners hit their balls in the water at the 12th. I nearly lost my ball at the next. You could have been forgiven if you feared the worst for our group’s prospects. Grammy winner Huey Lewis, who was injured but still following his long-time pro-am partner, Peter, looked a bit somber. (As Huey introduced himself on the putting green before the round, I told him almost giddily I knew who he was). Then something magical happened.

We walked back to a tee tucked between the tall pines that frame so many holes at Spyglass. The owners of a nearby house appeared with two guitars – one for Ben and one for Peter. A talented musician himself, Peter didn’t miss a beat as our small gallery of 20 or so filtered down the cart path. After a few strums of an E chord, Ben and Peter then started a bluesy improv. Peter sang some golf-inspired lyrics. 

The mood of our group changed immediately. Fans had their phones out. Dogs were running around, bathing in the sunlight. The music blew away the tension like a warm breeze. As the blues riffs faded, Peter stepped aside and turned things over to Ben. Steve requested a song to “get him going.” Ben strummed a beautiful melody while standing in front of Steve. Playing the notes crisply, he freestyled a song about the various payment methods he would accept for the closest-to-the-pin bet Steve had lost on the previous hole. It was hilarious. It was beautiful.

“He has the voice of an angel,” Steve said walking off the tee. 

The remainder of the round I put on a ball-striking clinic, practically placing the ball where I wanted it. Although there are plenty of potential pitfalls around Spyglass Hill, I avoided them. After 12 holes Peter told me he was shocked I didn’t have PGA Tour status. He told me I had the game to win and I needed to start believing it. 

Peter would repeat this often over the three days, cheering me on and sharing anecdotes about his career to illustrate how quickly good things can happen to a professional golfer. While I knew Peter would be entertaining and talkative, I hadn’t expected this level of generosity. I had considered what my role might be in helping Peter make his curtain call in a memorable way. Instead, he used his final start to lift me.

With the last tee time off the first tee at Pebble Beach on Friday, we were playing in prime time. The gallery was massive. Friends and family had flown in to follow. 95 percent of the fans were there to watch Steve. For me, Friday meant something else. It would be Peter’s last competitive trip around Pebble Beach. I opened with a three-putt bogey and spent much of the day fighting to stay in the game. Even with that internal battle, our group built on the fun we had generated the previous day. As I rolled in a 12-foot slider for birdie on 4, a lone fishing boat floated in Stillwater Cove. It looked like something from a Hemingway novel.

At 18, with the sun low and water glowing, Steve gathered us for a selfie. For a moment, we were four kids in our own world. The sun was low on the horizon and reflected off the glassy expanse of water. We all avoided sending our tee shots left into the Pacific.

I stood 240 yards from the green on the right side of the fairway and studied the crowd all the way to the green. Countless fans standing several deep lined the fairway between my ball and the green. A concert had begun near the clubhouse, a cover band loudly playing Neil Diamond’s “Sweet Caroline.” I waited through the first verse.

“What are you waiting for?” Ryan asked.

“The chorus,” I replied. 

After the crowd sang along, I refocused and hit a piercing 2-iron directly at the flag.

“Be good!” I said.

The ball landed softly on the front edge and stopped. It was a little unlucky, but this was now Peter’s stage.

It never ceases to amaze me how great players rise to the occasion in their final competitive moments. Peter played his third shot from about 130 yards to a pin cut a few paces from the left edge of the green, not to mention the Pacific. His tempo remained steady, and he hit an unwavering draw that stopped eight feet behind the hole. We waited for Peter to lead the group to the green. We were smiling, laughing, all of us soaking in the moment.

Steve rolled in a 40-footer, sending the crowd into a frenzy. As we high-fived and the crowd chanted Steve’s name, Peter was reading his putt. Fluff and Peter agreed to play one cup of left-to-right break. As if it was routine, Peter poured the putt into the heart of the hole. I applauded along with the crowd. A storybook ending at Pebble. 

The third round was cut day, and we were at Monterey Peninsula. Ryan was brilliant on the bag. I got off to a hot start, let a couple of shots slip away, birdied three holes coming home, and had a 40-footer for birdie at the last. I stroked it and watched with dizzying excitement as the ball rolled into the hole for a five-under 66. Fist pumps were thrown. High-fives connected. Hugs were shared. Everyone was laughing and cheering. That improbable birdie putt was one for all of us.

But golf is hard and Sunday was a reminder of how cruel the game can be. 

I played with two pros and an amateur as the winds freshened, the greens firmed, and the grind sharpened. Hundreds of thousands of dollars hang in the balance on a Sunday, and that reality sinks in somewhere during the back nine, when you’re running on adrenaline. A couple of misjudged winds and approaches on the closing nine led to a disappointing final round of three-over. 69-72-66-75 to finish T-49. 

Driving away from the course I hung my head. While it had been an exhilarating week, the back nine on Sunday was costly. Then came a text from Steve:

“Watched every shot. I’m sure you’re slightly bummed but this week was about grit and excellence. You inspired me as I witnessed it. I’ve seen a lot in my days and I went along for your soaring ride as I was drawn in to your incredible skills. You don’t have a weakness. As Peter kept saying, use this as a springboard forward, both on confidence and opportunity. Onward.”

Surreal. 

Those words. That opportunity. That land. 

That’s what awaits golfers at Pebble Beach. My dreams still drift over Stillwater Cove. 

One day, I’ll return.