But Mr. Sykes does much more than all of those. When he announces to each new arrival, “Welcome to the Thompson, I’m Gary, hotel ambassador,” he may be that rarity in this age of title inflation: someone who understates his own importance.
There are the little things, of course. Mr. Sykes and his colleagues at the Thompson, Samuel Asante and Verdell Butler, have learned to inspect arriving vehicles for stray phones and wallets, and to reunite them with their owners before either gets too far. (“Oh, you’re good, you’re very good,” said a man after Mr. Asante bent into a black Mercedes and re-emerged with a chunky billfold.)
There is also the matter of the neighbors. The affluent professionals who live in a part of town like the Gold Coast, which is just north of the downtown Loop, have a near-endless capacity for headache-making. If a situation escalates, they can bring down the wrath of the local authorities, who may take a sudden interest in the hotel’s permitting needs.
Mr. Sykes and his colleagues go to great lengths to tend to the neighbors’ care and feeding. They offer up the hotel’s valuable curb space for short-term parking, for example, and keep the valet podium stocked with dog treats, or Cheerios for canines with plus-size physiques.
When a grim-faced neighbor announced that she had just thrown up while preparing for a colonoscopy, Mr. Sykes was quick to regale her with stories of successful procedures past. “I’ve been there,” he said in his sunny baritone.
Then there is the problem of intelligence gathering. Mr. Sykes and his colleagues are constantly alert to chatter that a new arrival has lost a piece of luggage or is celebrating an anniversary, so that a complimentary cosmetic bag or bottle of champagne can be arranged. They are often the first to detect a whiff of discontent from a V.I.P., like cast members of the network television shows who bed down there during filming.
One afternoon, a smartly dressed woman stepped out of a small S.U.V. and trooped toward the doorway. Mr. Sykes soon identified her as an undercover shopper who rates hotels. “That was a test,” Mr. Sykes told me, beaming. “But we caught it.”
The giveaway, he said, is that these shoppers instantly accept almost every offer to help — with dinner reservations, theater tickets — no matter how elaborate. “We never know for sure,” said Steve Shern, the Thompson’s general manager. “We just remain consistent in our approach.”
Not that the Thompson doormen have been unaffected by the rise of smartphones. Uber is a particularly sensitive subject. The doormen make about $9 an hour, but their earnings can exceed three times that with tips.
According to Mr. Sykes, tips from hailing cabs once accounted for a quarter to a third of his tip haul, but Uber has sliced that amount by at least half. Even bad weather no longer ensures a line of cab riders. “I used to be able to say, ‘It’s going to rain today; I’m going to make money,’” he said. “Not anymore.”
For Mr. Sykes, it was partly the stability of door-manning that made it attractive. He came to the hotel, then known as Le Meridien, on a three-day assignment from a temp agency in 1993, having been laid off from a hair care products company after a dozen years there. He talked his way into a full-time job as a bellman, then ascended the ranks to doorman and eventually head doorman.
(Becoming a doorman turns out to be a bit like becoming chairman of the Senate Foreign Relations Committee: Few are hired directly into the job; they can spend years accumulating seniority.)
The memory of losing his job lingers to this day. “They downsized me,” he said. “I learned that word and it terrified me.”
Nearly a quarter-century into his tenure, he still checks a daily operations report early in the morning so he can get a jump on important comings and goings. By the time he attends a pre-shift meeting shortly before 3 p.m., he has committed the key details to memory. “I just hold the paper to be social,” he said.
There are certain tricks in the repertoire of any good doorman, and Mr. Sykes is an enthusiastic practitioner. Trick No. 1: Go out of your way to cultivate children, who tend to have outsize sway over their parents’ lodging decisions. Trick No. 2: Always sneak a look at the baggage label of an arriving guest so you can refer to the guest by name. (Trick No. 2.5: Make sure it’s an up-to-date, airline-issued label to avoid unforced errors.)
But achieving doorman greatness requires something more subtle. It is about walking a narrow emotional line. If your posture is too tentative, you will appear grudging and stingy, one reason that Mr. Shern, the general manager, preaches the need to make eye contact when a guest is within 10 feet, and always, always to “greet them before they greet you.”
If you’re too eager, on the other hand, you will come off as smarmy and transactional. Each gesture may be interpreted as a play for tips. Explaining how Mr. Asante became a first-rate doorman, Mr. Sykes said: “Sam learned to calm down and talk to the guests.”
In effect, Mr. Sykes’s method is to develop a profile of each person he encounters — which he is constantly updating — and calibrate accordingly. To the pair of middle-aged women on their way to Gibson’s Steakhouse, he was the vicarious wingman. “Have the Turtle Pie with ice cream,” he counseled. “It is very fattening but delicious.” (“We will, Gary. We’ll be thinking of you when we do it,” they replied.)
To the overnight business traveler intent on handling her own luggage — the “one-bagger” in doorman parlance — he is the discreet aide-de-camp, opening doors and tending to cars without belaboring the interaction. “Let’s get you inside,” he will say. “My brain is yours. Take what you need and leave me the rest.”
For Mr. Sykes, the key to this exercise is to think of himself as playing a very long game — one whose goal is to maximize the number of guests who return.
“I make people happy when they come to the hotel. They talk to their friends and family, then lots of people come to the hotel,” he said. “And that gives me job security.”
An app has many things going for it. It is fast. It is cheap. But an app can’t heed emotional cues the way a person would (even if some are working on it.). It has yet to host a successful dinner party.
Jillian Jocson, a Thompson concierge, said people grill her on how many tables in a restaurant have a view of Lake Michigan, or whether the beef is grass-fed. “As if I’m their own personal Yelp,” she said.
Mr. Sykes said lots of people tip him for no other reason than they happen to like him, in the way they might tip a street musician who brings them pleasure.
Already, the apps have come for legions of service workers, including some skilled ones. They will no doubt keep coming for more. But as long as humans remain social creatures, there will be businesses lining up to employ the likes of Gary Sykes.
“I like to give people the personal touch,” he said. “You can put anyone here you want, but you can’t put a Gary here.”