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A Day at the Barstool Classic with Michael S. Portnoy, Esq.

On Monday, I was able to play in the Barstool Classic in Boston. This was my second Classic (after Colorado), but my first time actually playing in it. I was invited to golf with the Portnoy family, and let me tell you it was an ADVENTURE. I thought I’d chronicle not only what a day is like golfing with Cousins Mike, Murray, and Linda, but also what a day at the Classic is like. 

First and foremost, I’ve been around golf my entire adult life, having caddied in high school and college (where I was an Evans Scholar). Since then I’ve spent a lot of hours on the course, and I can confidently declare, the Barstool Classic is one of the best run events I’ve seen IN MY LIFE. No kidding. 

So what follows is a day golfing with the Portnoys at the Barstool Classic. 

Buckle up. 

When you arrive at the course, they take your bags as soon as you get there and put it on a cart for you. Effortless. You check in and they hand you a dope cooler bag with the name of the course, a bunch of gift cards for golf shit, a branded towel, and a facemask with the Classic logo on it. Drip for days.

They have a bunch of food set up and alcohol not only at the check-in but near the practice putting green that served mixed drinks and food across the way. Of course, Cousin Mike stole the show by posing with a Truly like he’d never held a can in his hand his entire life.

You see people walking around wearing their best gear to impress Riggs in an effort to win the $500 Peter Millar prize (check Barstool Sports DM) which is WILD. The driving range is packed and the vibe is a buzz. Some of the outfits were, how shall we see … interesting.

Only one person, however, qualified as Best Dressed.

Before things got rolling, I got interviewed by our social team and unbeknownst to me, I have apparently been inducted into the Portnoy family. Quite an honor, being Dave Portnoy’s (other) sister.

Mike and Linda arrived, looking GOOD in their matching outfits btw, checked in and got dialed in and ready to roll. Riggsy was there to welcome his old radio partners and cousins with welcome arms.

On the practice green, Linda probably rolled 100 putts -- not even lying. We couldn’t win but she was ready to show up and show out. Some of you might not know but she is an award winning golf coach (coaching men’s golf) and played with Dave in a number of mother-son tournaments. The chipping area was mint, the greens were rolled and it was clear the courses were going to be in great shape. 

We teed off behind Dana and his family, which was hilarious. There were pretty much coolers on almost every tee box with Twisted Tea, Truly of every flavor, and a cart girl that roamed around handing out free snacks and drinks as well. 

Can you tell they thought of everything? 

The golf was slow but it was GOLD. We had a cameraman follow us most of the way through, along with a social media person, capturing every move we made. 


Off the first tee, Cousin Mike lost one in the woods. Cousin Linda was heckling on the first tee as well. Murray was making fun of Mike’s athletic ability. I mean, what did you expect? Mike’s wife is a golf coach and his son is the U.S. Open Champion. TALL EXPECTATIONS.


Alas, the heckling clearly rattled poor Mike, who whiffed 3x in a row once he got into the fairway. He mashed probably 10 to 15 shots before I hit my approach shot. Just waiting, and watching, and laughing. Experiencing the pressure of a cameraman RIGHT behind you as you swing. 


Linda was taking this round EXTRA serious; she didn’t even want to give two foot gimme putts at first. “We’re playing everything down [until it’s in the hole]”. 

Hardoooooo. But then I missed my first two footer for par and I knew it was going to be a long day. 

We also had a group not taking part in the tourney playing behind us since we were the last tee time. They were IMPATIENT. These mutherfuckers hit into us MULTIPLE times even though it was obvious that we were waiting on every hole for Dana’s group. Linda, former Swampscott High coach, decided to lay the smack down on them. After one incident in particular where they almost hit us with a ball, she looked at me with a cheshire cat grin and said “you want to see me get REALLY nasty?” 


Then she noticed this group had an American Flag on their cart, which in her opinion meant they were probably packing some heat. 

Instead of getting shot, she took two extra cookies from the snack shack. 

REBEL. Love this woman so much. 

By that point Mike was done ACTUALLY golfing. He hit grounder after grounder for the first full nine and that is tiring and dejecting. He was frustrated and tuckered and ultimately just decided to drive ahead and hit tee shots and pick up his ball from the fairway. Don’t hate the move.

This continued til the end of the round, when he finally got his second wind, competing in a full hole for the first time on the back nine. He was in better spirits with the clubhouse in sight. After the round we debriefed and he, like the astute observer we know him to be, complimented me on my swing and golf abilities even though I had an incredibly off day. 

We had a socially distanced dinner out on the lawn as the event wrapped up which was perfectly set up, and had food that would rival normal high end restaurants. 

I dare say, it was one of the best events I've ever been to.

So anyone who’s considering golfing in the Classic? You will love it. It’s so well run and so fun, you can’t help but have a good time. 

Even if you’re Cousin Mike. 

P.S. Lotta people asking for my swing. It is below.