Taylor Swift Was Seen Once Again Tipping Service Workers Like She's The Modern Day Frank Sinatra. More Celebs Should Follow Her Lead

(Sidebar - I love how you can tell she asked the bigger guy and the lady watching the monitor if she took care of them already, and they said no, so she pulls out more bills and greases them.)

I love seeing this so much. 

And before you clutch your pearls and scream "it was staged", let me stop you right there. Because this has been Taylor's m.o. since pretty much forever. 

She went into hostile territory in Foxboro a few years ago and was slinging Benjamins to all the Gillette workers (shout out to my girls Cindy, and Gabby). 

The owners of my favorite restaurant in New York tell me she tips $1300 on her bills and hands all the bussers and hosts $100 bills. 

This is the kind of flex Taylor really needs to hone, and become known for. 

She already has pretty much every other accolade you can have. Being known as "the best tipper in the world" is elite territory. 

It not only means and shows you have crazy disposable income. But it also demonstrates you're a generous, considerate person. Not a cheap bastard. (I think it's safe to say cheap people are universally hated because they are the absolute worst.)

This kind of behavior hasn't been seen since the days of Frank Sinatra. 

One of the best parts about being in the hospitality industry is meeting the different people I've gotten to know over the years around the country. Especially the old-school guys. 

The iconic Tavern on Rush, (the original, not the reopened one) was once owned by a legend named Marty Gutilla. 

I got to know Marty over the years, before he passed away in 2018, and as anybody who knew him would tell you, the man knew how to tell a story better than anybody. And he had thousands of them. He was like a mentor to me and I loved him very much. When he was young, he used to own the best clubs on Division St. (Which was the spot back in the day in Chicago). Just around the corner from "the viagra triangle" at State and Rush streets. There he met pretty much everybody who came through Chicago, as his place "Faces", and "The Playboy Club" (Hugh Hefner's first playboy mansion and club) were the hottest spots to be. From there he opened up Tavern on Rush, across from Gibson's, with Phil Stefani, and between that and Faces, he got to know and become friends with every politician, musician, and movie star you could think of back in the day. Sinatra included. 

The Sinatra stories Marty used to tell me would make the greatest book and movie ever. The guy was even cooler and smoother in real life than he was portrayed by the media. I could, and would, sit there and listen to him tell them for hours.

One of my favorite things that always stood out in those stories was how Sinatra never flaunted his money or power. But he was always so generous whenever it came time to pay for something or take care of just about anybody.

The legendary stories still float around Las Vegas and Hollywood of course, but hearing them direct, from somebody I knew well, about him rolling into spots in Chicago like The Pump Room, or Gene and Georgetti's, and throwing everybody working in the place a couple $100 bills was awesome. 

That would be awesome today. But even more so back then when $100 was worth big bucks.

The guy used to read stories in newspapers that would break his heart, and he would anonymously send gifts and money to families hit with tragedy to help them out.

He used to give millions to children's hospitals around the country.

Burt Reynolds once told a great story about Sinatra on Johnny Carson's show - 

While out to dinner one night at the popular LA eatery Nicky Blair's, Burt Reynolds caught the eye of Frank Sinatra, who was dining with his entourage. Summoning Reynolds, Sinatra invited him to a poker game he and his friends would be holding in the restaurant's kitchen after their meal. 

When he joined them, he found them "seated at a big round table in the middle of the kitchen, with all the waiters and busboys rushing back and forth." 

As Sinatra called five-card stud, there was a "big crash," as "an unlucky busboy had dropped a tray of glassware." As Reynolds recalls it, the owner, Nicky Blair, came in "yelling at the poor busboy," and Sinatra did not approve.

"How much do those glasses cost?" Sinatra asked his host.

"I don't know, Frank, a few bucks apiece."

Sinatra nodded to his two bodyguards, and one at a time, each counted out $3,000 in cash and Jilly handed it to Blair. He handed another $1000 to the busboy named Hector, "Now bring me three grand worth of glasses," he said.

The confused restaurateur started sending in busboys with trays full of empty glasses. Sinatra asked one for his name — it was Hector — and said, "Hector, break 'em!" The busboy did as he was told "until the floor was covered with broken glass."

"Frank told Nicky, 'If I ever come in and don't see Hector, I'll never come back."

At that point, before a card had been dealt, Reynolds got up to leave.

"'Where the hell are you going?' Frank said. "'Home,' I said. 'I got my Sinatra story.'"

The only other big name, "celebrity" I hear get talked about by people in the service industry like this today is Dana White. 

Anywhere you've been that Dana White has been, you can ask the manager or staff for a Dana White story, and they'll almost always have a good one that involves him throwing ridiculous amounts of cash to the staff.

My friends in Vegas told me that Dana White used to love playing cards, mainly baccarat, at The Palms. He's allegedly a really good card counter, and took them for a shitload of money, so they banned him. He would routinely tip the dealers, table servers, and anybody else on staff that he could $10,000+ a piece whenever he played. So they obviously all loved him. (Plus they said he's always very polite and friendly). When the workers found out he was banned, they threatened to stage a walkout and file a union grievance, demanding he be let back in to play. The casino complied and he got to come back and took great care of everybody. 

(Sidebar - the flipside of that story, from pretty much anybody, anywhere, that I ask who is the worst tipper, is almost 100% of the time Tiger Woods surprisingly. Which is really sad.)

I don't think we needed any more evidence that Taylor Swift is a great human. She takes care of her people better than pretty much anybody- 

And it's great to know that she sees the value in the people she comes in contact with in everyday life, and enjoys wetting their beaks. It's not just a great gesture, it's great karma. Hopefully more celebrities start to take notice and follow her lead.