Marriage proposals, Tiger’s favorite drink and a warm smile: Meet the soul of Pinehurst

Sheila Wilson

Sheila Wilson, the bartender at Pinehurst's Cradle Crossing, and her many fans.

Courtesy of Sheila Wilson

Every job in golf is a good job. But some gigs — like the bartender at Pinehurst’s Cradle (below) — make us especially envious! To browse more Best Jobs in Golf, click each link here: USGA Museum Curator | TaylorMade content creator | Luxury helicopter pilot | Titleist club builder | Superintendent’s dog | Course designer | Gold Putter Vault guardian | Social media content creator | St. Andrews Starter | Callaway equipment innovator | Course photographer TravisMathew executive


Before we get into the story about how John Daly drinks Crown Royal as if it were swing oil, and the story about the fellas who wanted their picture taken sans bottoms, and the tales of $500 tips and marriage proposals, Sheila Wilson is going to make us a drink. Our own drink. She’ll name it, too. 

All of it maybe tells her story best.

So pull up a stool. 

I hate to put you on the spot. But if I give you my drinking background, can you come up with a drink for me? 


halfway house pinehurst
Pinehurst unveils a fittingly awesome new halfway house dubbed the Cradle Crossing
By: James Colgan

I don’t know if it helps, but I’m a reporter for a golf magazine. I like rum, any kind of juice, not something sour. And I’d say I’m probably more of a beer drinker. But what would you come up with?

“OK, so a little sweet, right?” 

Yeah, yeah. 

“OK, um, you would love the Cradle Sunset. People who drink more beer and don’t drink like heavy bourbon and don’t like a sour, Cradle Sunset, I would recommend. But something with probably Captain Morgan, spiced rum, and we do that with — you would actually like the Blue Driver, to be honest with you. You could do something basic — Captain Morgan and probably another ginger ale. No, I would do a Malibu rum and pineapple with a splash of tequila for you. Do you drink tequila? Can you?”


“Oh, OK. That’s what I do for you. Malibu rum, splash of tequila — or do the opposite of the Cradle Sunset, with some pineapple.

What kind of fun name would we call it? If it helps you, too, I also have a very long Polish last name. 

“I was going to say — how do you pronounce that? Yeah, I saw it. How do you say your last name?”

Sheila Wilson
Sheila with some happy customers. Courtesy of Sheila Wilson

It’s Pea-uh-stOW-ski.



“Ooh, we got to have something with a ‘Ski’ in it. You got to have a ‘Ski’ in it. [Laughs.] Everybody that I know that’s Polish has the ‘Ski.’ Um, or the ‘Nick Ski.’ [Laughs.] Got to have ‘Ski’ in it. We got to put the ‘Ski’ in it. The ‘P Ski,’ yeah, yeah, yeah, something like that. We got to have that in it. Or the ‘Rum Ski.’ That’s it! The ‘Rum Ski.’ That’s it. ‘Rum Ski.’ OK, I was trying to think what liquor is in it. The ‘Rum Ski.’ 

“That’s your drink, baby. Absolutely.”

Let’s pause here and do our hellos. Gang, this is Sheila, and she’s the friendly face at the year-old Cradle Crossing, an aptly named bar at Pinehurst — it’s midway through the resort’s short course, the Cradle. Sheila’s a mother of three and a former grade-school teacher and she has become so much a part of one of the world’s finest golf destinations that they’ve singled out her and her skills on their damn webpage. If the golf courses are Pinehurst’s drink, Sheila is its straw.

OK, everyone good?

Sheila has some stories, and she tells them better than we ever could. 

‘I always tell people, they go, When do you close? I go, Whenever you stop drinking’

Sheila Wilson
Another great day, another great group at the Cradle. Courtesy of Sheila Wilson

What does a typical day look like?

“Well, we come in at 10, and we have the bar open by 11. And there’s already — depending on what day it is of the week, like yesterday, by the time I got here at quarter to 11, I was serving double-shot Transfusions by 11. Starting at 11 and nonstop till 10 o’clock last night.” 

Wow, OK. 

“That was a Sunday. And that’s usually pretty slow, but on the average, you know how everybody sort of is, on average, probably 250 Transfusions a day out here. And then, they don’t count my speciality drinks that I created when I opened the Pine Cone [the longtime bar cart at the Cradle] — we have the Cradle Sunset; of course, I still have the Pine Cone because that’s an all-time favorite. So we’ll go through all the specialty drinks and things like that. But starting around 11. We close according to volume. I always tell people, they go, When do you close? I go, Whenever you stop drinking.” 


“Because you know, they got the fire pits going on. That’s the beauty of it when I’m out here working, you pretty much control — if there’s a big crowd, like last night, I had some military guys out here and they hung out till 9:30 or 10. Finally, I said, all right, you gotta go. I got to shoo you; it’s 10 o’clock. But it just depends. There is no set time. There’s nights where we close at 7:30, and then there’s times when we close at 10.”  

What days of the week do you work?

“It just varies according to our schedule. I’m usually out here four days a week, four to five days a week. And then there’s two or three other people that kind of come in and help out, which is good because I just got back — I was in the Bahamas for the NCAA women’s tournament. So I went out there, to Ocean Club, to watch. So I had a week off. My one week off. Then I always take a week off in June because I work with the U.S. Open. So I go out and spend a week helping out with the U.S. Open wherever it may be.” 

‘We all turn 5 after a while, after a couple Transfusions’

Sheila Wilson
Sheila, at your service. Courtesy of Sheila Wilson

When did you start working at Pinehurst? 


How did you get connected there? Why did you decide to start working there?

“I was teaching full time, and so during the summer, I would work the beverage cart and it was a blast. I had so much fun. So eventually, after a couple years, I retired from teaching and came on here full time.” 

What level of teacher were you?

“I was K-6, elementary, and I also worked with special needs kids, so my minor was in child psychology. I always tell people, especially when it gets a little rowdy here in the evenings, I say, my degree is coming in handy, we’re good.” 


“Because they’re, ‘What, you got a …?’ And I said, yeah, I still use it from time to time. We all turn 5 after a while, after a couple Transfusions.”  

‘And the more he drinks, the farther his drives got’

Sheila Wilson, John Daly
Sheila and John Daly. Courtesy of Sheila Wilson

Clearly you have a mixing background. Did you tend bar before?

“Only in college a little bit. Just in college. No, nothing — I’m an elementary teacher. But in college, of course, you always work a bar and stuff like that. But I do travel a lot, like I said, through golf and go to some of these resorts. Like I said, I just spent a week at Ocean Club and so you get a feel of tasting different drinks. And I’ve traveled around the country, I went to Paris for the Ryder Cup a few years ago, I’ll go to Rome next year, so you taste and you get to experience a lot of really cool, different drinks. And you talk to people. People are like, no, this is good. Or, I like cranberry, but I don’t know what to mix with it, so you kind of come up with things. Love talking to people about what they drink. Oh, and they got some crazy names. I wanted to add more, but they’re like, nope, can’t call it that, can’t call it that.” 


“Like, I used to know Tiger Woods’ favorite drink was the Duck Fart. I can’t put that on the menu. But that’s what he likes to drink. And then, god, there’s so many. Of course, I’ve met quite a few and I’ve experienced spending two or three days with John Daly several years ago. He likes Crown Royal, on the rocks. And the more he drinks, the farther his drives got.”


“Now he’s a hoot. I enjoyed spending time with him. I was kind of his handler. His manager goes, whatever he wants, you go get. Got it. 

“And I’m not a big drinker, but I do like tequila, but I’m not a big, big — no, not all out, bleh.”

What was Tiger’s favorite drink again?

Sheila Wilson, Emmitt Smith
Sheila and Emmitt Smith.

“It’s called a Duck Fart. I used to remember what it was — I had a long list of everybody’s favorite drinks. I think it’s a mix of — it’s almost like a shot. You have to look it up. I looked it up one time because I’ve met some of the players that come through here; like Webb Simpson will come through and stuff like that and we’re talking about drinks. And Bill Haas was here not too long ago. And of course, he had some great stories about Tiger. But yeah, I think it’s like a shot of something, but it’s a layer. I cannot remember, but yeah, that was always something that he liked, was a Duck Fart. 

“I wanted to create something with Medori, which is green. … On course 2 and course 4, we’re just famous for — it’s called the Love Grass. This really thick grass, just everywhere, especially on No. 2. And if you land in it, I don’t care how many times you kick that bunch of grass, the ball doesn’t come out, you know what I mean. You just, uh. So I wanted to call it the Love Grass or something like that. Make it green. But aka, people always say, ‘Where did your ball go?’ ‘It went in the s**t.’ Well, I can’t put that on the menu. Noooo. But yeah, that’s kind of the aka, the Love Grass. Because once it’s in there, you’re done.” 

‘It’s a good thing, buddy, you can sing because you’re terrible at golf’

Sheila Wilson
More good times with more good people. Courtesy of Sheila Wilson

You mentioned you have a list of pro golfers’ favorite drinks. How many players have you served?

“There’s been a few that have come through here. Then, of course, there’s always this random — every now and then you have other athletes. Not necessarily celebrities that come through here over the years that I’ve been here but athletes — basketball players; I had the Lakers one time. It was a hoot. I went, OK — huge, but I loved them, great group of guys. Chris Berman, terrible at golf, terrible, terrible. I had him on course 2 a few years ago, but no, he’s a hoot, he’s fun to hang out with and talk to and take care of. Needs to work on his golf game, but he’ll be all right. And a lot of coaches. You know, Mike Ditka. Bourbon, straight bourbon. He’s a bourbon kind of guy. Lot of college coaches come through here. I missed the fact that Nick Saban came through a couple years ago and I didn’t get to meet him. Obviously I’m a big sports — I went to N.C. State and I love my sports. But just athletes. Danica Patrick. Good golfer. She came through a few years ago. She’s an avid golfer. 

“So yeah, there’s quite a few, and they’re just great people, they really are. You just treat them like — that’s the thing, I don’t go out of my way. Who was it? I cannot think of — it might have been Ben Roethlisberger or one of those guys or something and I don’t mess with them. They just want to come here and hang out, have fun, relax. And I say, you want your picture taken? And they say, no, but I want my picture taken with you, and I go, OK. [Laughs.] 

“But then you got the Mannings that come through here every so often. Now they’re a hoot. What you see is what you get with Peyton and Eli. And Archie. They’re all real — very competitive those three, among those three. So you just have fun with it and you don’t — like I said, I treat them like a regular golfer. They’re just here to golf and have fun. And if they suck, I’ll tell them that. It’s a good thing you can play whatever because you’re terrible at golf. 

Sheila Wilson
Sheila in her element. Courtesy of Sheila Wilson

“Oh, and we have singers that come through. I did tell, I think it was Morgan Wallen a few years ago, but I told him, I said, it’s a good thing, buddy, you can sing because you’re terrible at golf. They were here during Covid when they weren’t traveling so they brought a big group here and came and hung out. And we had a blast on the Cradle. We did, we really did. They kind of had it to themselves for three hours one evening. And I didn’t realize Jake Owen was on a college team. He was good. And Morgan was with them. There was a whole handful of them. Shay from Dan and Shay. We definitely had a blast on the Cradle one evening with that group. Good group.”  

‘The ongoing thing is, how many proposals do you get a day?’ 

What is the funniest thing a customer has said or done?

“Funny or dirty? [Laughs.] It can get a little dirty. Funny. Ha! There’s a lot of jokes that get told out here that we won’t mention.” 


“We’ll have guests that come up and ask for certain drinks and I’ve never heard of them before in my life. Like Windsor Pisser. I don’t know what that is. And then, of course, other drinks. Like, they’ll have specialty drinks at their club — that’s always a hoot to hear. The Dick in the Dirt drink, stuff like that. I go, what? That’s kind of fun to hear different names. They have their own little club drinks.  

“The other thing is, the ongoing thing is, how many proposals do you get a day?” 


“I get a lot of phone numbers during the day. [Laughs.] That’s always the joke, They come and go, how many times has this happened to you today. Well, a lot. Or business cards. Or phone numbers written on a $20 bill. Yeah, I get quite a few.” 

Sheila Wilson
Sheila with a young customer. Courtesy of Sheila Wilson

What’s the strangest thing a customer has said/done?

“I take a lot of pictures of people — they want their pictures made out on the Cradle and stuff. And the strangest — well, it really wasn’t the strangest; one of the weirdest — is their tradition is wherever they go, they wear matching boxers. And they drop their pants to have their picture made.” 


“And I said, please tell me you have boxers on under your shorts because don’t do this to me if you don’t have anything on under those shorts.” 


“So that was kind of weird, taking pictures of grown men in their underwear. That’s their tradition — wherever they play, they have to have their picture taken in their underwear by the bar. I’m like, OK. And I happen to be the lucky one to do that. It just depends on the evening — a lot of crazy stuff happens.” 

What is the biggest tip you’ve ever gotten?

“Five-hundred dollars.”

‘I always tell people, when you play 2, don’t get excited for about 5 seconds’

Do you ever get to play the courses?

“Yeah, yeah, I do. I don’t play out here as much. I try to play — because I’m also a member, so I get to play 2 and 4, which 2 kicks my butt. I tell people all the time when they play 2, you’re going to say FDR. And I said, out of respect, say it that way. Because that’s the nice way to say it. You know what that means obviously?”

I don’t! Tell me. 

“OK, who designed the course? Donald Ross. So F-D-R. [Laughs.]” 

[Laughs.] All right, all right. 

“One time I said that would be so disrespectful, but if we put FDR on a hat, we’d sell the crap out of it. Yeah, we would. I don’t think his family would appreciate that. Because the course is a great course, I love Donald Ross, and it’s amazing the things he’s accomplished and all the courses he’s built, but 2 is all turtleback, it’s all — I always tell people, when you play 2, don’t get excited for about 5 seconds; I said count, because it’s probably going to roll off the green. So I said do the one, one-thousand, two, one-thousand because nope, it’s going to roll off. And I said, don’t go for the pin, go for the center. I said Donald Ross did this dirty, little trick. Makes it very difficult to stay. And so that’s where the FDR comes from.” 

‘This is the happy place at Pinehurst’

We’re about 45 minutes in now, and at this point, we’ve taken up too much of Sheila’s time. She is a busy woman, and there’s no tip that we can give that can possibly compensate her for all that we have learned. But we have one more question. It’s the reason we came.

Why do you think your job is one of the best in golf?

Sheila Wilson
Sheila and Barstool’s Sam “Riggs” Bozoian. Courtesy of Sheila Wilson

“For one, everybody, once they get on the Cradle, attitudes change. It’s stress free. My job is to de-stress everybody, I guess, from coming off of 2 or 4 or whatever course. And there is no stress because, you know, I always tell people, take your shoes off, relax. And it is. It’s a completely different — the whole golf attitude, once players get out here, is just so chill. There is no temper, there’s no worry over the score or pace of play. You know that. They get to hole 3 and they’re going to stop and sit in the adirondack chairs, have a drink and then, OK, well, we’ll play some more. You know, shoes off. Everybody’s happy. Everybody’s relaxed. We talk. …

“It’s just a cool place to work because once everybody gets here, of course, they’re in love with the Cradle, they love the Cradle, they love the bar. And that’s the biggest thing — very relaxed atmosphere. That’s probably the biggest because it’s just happy. This is the happy place at Pinehurst.”   

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Nick Piastowski

Nick Piastowski Editor

Nick Piastowski is a Senior Editor at and Golf Magazine. In his role, he is responsible for editing, writing and developing stories across the golf space. And when he’s not writing about ways to hit the golf ball farther and straighter, the Milwaukee native is probably playing the game, hitting the ball left, right and short, and drinking a cold beer to wash away his score. You can reach out to him about any of these topics — his stories, his game or his beers — at