Trump Concierge Jay Baldridge Talks Hotel Whales

As lead concierge of one of the ritziest hotels in town, Jay Baldrige has his hands full with all sorts of requests for dinner reservations, night club entrances, and other outlandish demands and desires of the richest Whales visiting the Windy City.

So tell me about what you do as a concierge?
I do everything from greeting guests to making dinner reservations to arranging a helicopter pickup at Midway. Helicopters, jets, everything. It doesn't happen that often, but often enough where we have to know the procedure and how to take care of it. A lot of people who have that request are usually from places like New York or Los Angeles where there's helipads all over downtown. Unfortunately in Chicago they're all owned or operated by the government so they're for hospitals or the Coast Guard or so forth. The closest place is Midway Airport. So often time when we start to explain that it kind of gets shot down. The whole reason for helicopters is that they think it's going to be a lot more efficient. If they're coming in from the suburbs we have some high profile guests that do some performances out there but when we explain they're going to have to land at Midway Airport and they have another 45 minute drive in then it doesn't make a lot of sense. That's one of the problems we have in Chicago but from what I hear that might be changing.

Can you tell a whale right away or are they more inconspicuous?
They're usually inconspicuous. One customer was from Russia, I believe Russia has the highest concentration of billionaires in the world. We had a quite-wealthy guest who wanted to take a day trip to Niagara Falls, but they wanted to do it within 24 hours and they would have to get a visa to go into Canada so we decided to get them to Buffalo. When we quoted prices for a private jet to take them over there, they were flabbergasted to why it would cost so much in the U.S., he owns a whole fleet of jets in Russia and in Eastern Europe it doesn't cost nearly that much. But a lot of the high-rollers we get are actually from the states. People in the TV business, production companies, business owners, athletes. A lot of times pricing never comes up, it's thought of as tacky. You get a snide remark shot back of "did I ask how much it cost?" Once you hear that you never want to hear that again.

Where do people ask you for reservations the most?
Usually the Michelin-rated or the top-rated restaurants in Chicago. Ever since we started getting Michelin ratings it's really put us on to the culinary world. We were really overlooked and we're now gaining ground on it. A lot of our world-renowned chefs such as, well Charlie Trotter is retired and went back to school, but Grant Achatz, Homaro Cantu, Rick Bayless, have TV shows and are on a world stage. When people see those and see that the Michelin guide is now in Chicago, a lot of people look through that guide and request tables at those restaurants. The more popular ones are the ones that are less formal, the dining clientele these days is a little more for comfort than for lavish extravagance. Restaurants like Everest or Spiaggia are very elegant restaurants with coat and tie required, whereas some of the newer more contemporary restaurants such as Alinea and our restaurant Sixteen are a little more contemporary, a little more modern, and a little more comfortable for the guest experience. The first thing they say is "do I need a jacket? I didn't pack a jacket." People don't pack jackets anymore. There are occasions though, one high-profile guest had me plan his anniversary with his wife and the whole itinerary had to be planned via text message. He actually wanted to go to Spiaggia, a very elegant restaurant that he thought his wife would really enjoy for a birthday or a special day. We made arrangements at Spiaggia, had a chauffeur at the door, and came back to the hotel later. His prerequisite for the evening was to give his wife a brand-new BMW convertible for her birthday – you figure out how we're going to do it and how the rest of the evening ends, and we have to do it via text message. I just said "this is where you have to be at this time, have the car delivered to the hotel and I'll make sure it's parked. It'll be kind of my Oprah Winfrey moment." He kind of laid the rest in my lap, it turned out to be an exceptional evening. It was my idea to make her the celebrity of the evening, she always lived in the shadow of her husband. Instead of everyone addressing her husband they would address her first. I got her dozens of red roses that were just handed to her by complete strangers. At the end of the night we had her husband on the driveway, had our staff lined up, and had the convertible with the top down blasting this club song for happy birthday. Of course more champagne and the cherry on top was being presented with one of our best hotel suites. By the end of the night she was in tears, she was just completely blown away. That was a lot of fun.

What are the top five reservations?
Alinea, Topolobampo, Sixteen, Gibson's is always on top for steakhouses, and Girl and the Goat. With reality TV, all these chefs are on a global stage now, people recognize them and like their personalities and they want to see if they'll enjoy their restaurant and their signature dishes. The one I'm most excited about is Grace.

How about nightclub requests?
Some of the clubs that really deliver for us are going to be The Mid, or Cuvee is a great spot that can provide some of that privacy and exclusivity. Sometimes they'll come out with a blanket statement like "we're looking for the best nightclub." That usually requires a good bit of follow-up: "Are looking for a dance club? Are you looking for an ultra-lounge? Are you looking for a DJ set?" There's so many different varieties and when you go around you'll see a different clientele at every one of them. Our job is to narrow it down and really see what kind of experience they're looking for. We have quite a bit of doormen and VIP hosts and managers in our phone book that we just dial up and put them on the guest list.

What are the most outlandish requests you get? Anything that you run to your friends to tell them about?
We start to get a little numb to a lot of those requests. One of the most interesting was a request for wild animals. We had to ship them overseas and it took about three months of work to have the animals quarantined and making sure they were well enough to be shipped, which involved getting certification from the USDA. They wanted them to be within three months old.

What was the most expensive request you've ever had?
Probably arranging for a fleet of Mercedes Benz's. The cars were going to be on call for four days and came to about $60,000. That was a pretty big charge I had to put through, making sure I hit the right amount of zeros.

I wonder how much they just sat at the hotel.
They sat quite a bit. The original quote was $80,000 but sometimes we dismissed some of the drivers.

Are there any restaurants that you have a hard time getting guests into?
Quite a few, actually. Some of the ones that aren't even on the radar are highly-coveted and that's a lot of the reason why guests want to go to them in the first place. One of the things I say to guests, especially with nightclubs, is "if you want to go somewhere that's not busy there's a reason why it's not busy. If it's packed it's going to be a fun place to go to." That goes with restaurants as well. Lucky for us, we have a lot of great relationships in the industry that gives us a little headwind. In the end we always come up with a compromise that makes everyone happy.

Do you get any crazy room service requests?
A lot of people look at the room service menu and the Sixteen menu and start ordering off-menu. Sometimes people want boxes of wine delivered from vineyards. They often see the menu at Sixteen and want it delivered to their room. One of our best dishes is called the Japanese breakfast, it's an amazing dish we had featured in Virtuoso Life Magazine in their fall food and beverage issue. People will go to Sixteen and look at the menu, then close it and say "I'll have the Japanese breakfast" even though it's not on the menu. That's more extravagant than ordering the most expensive thing on the menu. It's on the in-room dining menu but not on any other menu in the hotel. I love when guests don't take no for an answer because it gives us a challenge.

Are there any other off-the-menu requests that people ask for and you do?
Quite a bit. People have dietary restrictions and ask for carrot puree soup. It's nowhere on the menu but we make it. Chicken noodle soup too. We have concierges and bellmen that search the city and have it delivered to the room. We had one guest that had a very particular diet, he had just had surgery and was on a very organic no-additive diet and we had to go grocery shopping for him for the next four days and prepare soups in house for him.

Is there anything else people ask for that you can't do?
The only thing that every luxury hotel concierge could wish for in Chicago is a fleet of luxury yachts. We have a lot of guests that want that big Miami 40-to-55-foot Sunseeker and unfortunately we don't have the market in Chicago. We have short summers here. There's one company that actually has a great fleet of Sunseekers but they don't accommodate as much. We have guests that are looking for huge yachts, we have Lake Michigan and a lot of the guests that aren't familiar with it think it's the ocean. As fun as Lake Michigan can be, it can also be very dangerous. It's really not possible for anyone to rent out these large yachts that they have in Miami or L.A.

Do some guests never want to leave?
A lot of the guests that stay in the hotel end up buying in the building. Studios start out around $500,000, that's roughly 600 square-feet. The penthouse is just over 14,000 square-feet and the asking price is around $30,000,000. We have a lot of guests that come in and say "I could write a check for it right now but my spouse will kill me."

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