NEW YORK - This night before Christmas, not far from where Clement Clarke Moore wrote A Visit from St. Nicholas, Isaac Simon will make his rounds, as he has most Tuesday evenings for six years.
Simon is not Santa. He is Jewish. His sleigh is a white Ford commercial van loaded with soup, bagels, milk and oranges. His sack is a black plastic trash bag filled with clothes. His recipients are those who will spend Christmas Eve on the street on the world's richest island.
'Anyone out there on that night,'' he observes, 'is taking homelessness to a whole sad new level.''
Simon, 41, is both a financial adviser who manages $160 million and a volunteer driver for the Coalition for the Homeless. As servant of the rich by day and the poor by night, he bridges a breathtaking material chasm.
'It's a city of extremes,'' he said last Tuesday as he drove the van through holiday traffic.
This year, as Christians mark an event that turns on a housing crisis - no room in the inn - it's a nation of extremes. A few live at unprecedented heights and in unparalleled splendor; many struggle to pay the mortgage, make the rent or find a place to stay.
In New York, where three high-rise apartments not even ready for occupancy are under contract for more than $90 million each, the homeless shelter census has passed 51,000, the population of Charleston, capital of West Virginia.
Although a national survey released last month found homelessness to be down, it's increasing in many places where upscale housing is booming, such as New York, Los Angeles and Boston.
Sometimes, there's a cultural conflict.
Two L.A. City Council members, spurred by complaints from residents who blame street feeding of the homeless for crime, noise and filth, have called for a ban on such programs. More than 80 municipalities have adopted or seriously considered similar prohibitions, according to the National Coalition for the Homeless.
In Honolulu, a state legislator last month destroyed shopping carts of the homeless with a sledgehammer, saying he was 'disgusted.' In Miami, residents' complaints led to proposed rules for the homeless in the burgeoning downtown, including no cooking fires in parks and no tents on public property.
The contrast between rich and poor has never been more obvious. Though the four-story chateaux and palazzi of the Gilded Age were invisible to the tenement poor a century ago, today there's no escaping sight of the high-rise rich.
In New York, their apartment towers are visible from Highbridge in the Bronx, where 43% of residents pay at least half their income in rent; from Jackson Heights in Queens, where almost 10% of housing units are severely overcrowded (more than 1.5 persons per room); from Coney Island in Brooklyn, which has a foreclosure rate approaching 40%.
From a penthouse, you can follow Simon's route around Manhattan, starting on the West Side and moving north to Harlem before circling back down Fifth Avenue, past the Metropolitan Museum of Art, FAO Schwarz and the Plaza Hotel.
Better, though, to imagine riding with him Tuesday night, as the shoppers retreat, the streets empty out, and the temperature drops on what for some is the darkest evening of the year.
7 P.M.: Broadway and W. 51st Street
Coalition for the Homeless vans feed hundreds of people on three routes 365 nights a year. Isaac Simon drives the uptown route almost every Tuesday.
The van pulls up to a regular stop, and the homeless materialize, lining up with their bags and backpacks. Their faces are shrouded by hats and hoods. Their bodies are tense against the cold. Each person is handed a white plastic bag and offered a pint carton of milk, an orange, a container of warm soup and a bagel.
'We appreciate it,'' a bearded man, Richard Connors, tells Simon. 'Are you kidding? What else would we do?''
Simon chats easily with these people, breaking the ice with a comment about someone's team jacket, or how cold it is. It's like his day job, he says: 'Instead of schmoozing with people with 10 million, I'm schmoozing with people with negative 10 cents.''
7:15 P.M.: W. 40thth Street, behind Port Authority Bus Terminal
In addition to feeding more than 100 people a night, Simon has become haberdasher to the homeless, dispensing new and used clothes at each stop.
After watching some Mexican day laborers shiver in line one night, be began giving away his own used clothes. Word spread through his office, and now his file cabinets are filled with bags of clothes, from sweatshirts to Armani jackets.
On the street, Simon acts like the type of itinerant peddler on whom Moore based his version of St. Nick. As the food is handed out, he moves along the line with his bag, helping people try on coats and sweaters and ripping open packs of gloves, socks and underwear that he purchases in bulk at a Korean discount store on 27 th Street.
Last Tuesday night, he waited on a rotund woman who said she needed a winter coat. From his bag he pulled one after another, each of which the woman haughtily dismissed.
'Size 8?'' she said after he handed her one coat. 'Do I look like a size 8?''
Finally, after lavish flattery from Simon, she agreed to keep the last one in the bag.
'No pictures,'' she said. 'No name.'' Like many others on the route, she values her anonymity.
7:45 P.M.: W. 79th Street and Riverside Park
Each stop has its regulars, including young and old, fit and infirm, white, black, Hispanic and Asian.
At 51 st Street, a heavyset disabled man sitting on a bench calls himself The Boss. As such, he does not go to the van; a volunteer brings food to him. Since he is The Boss, he does not say thank you.
Behind the bus terminal, there is the man Simon calls The Coat Man, because he never seems to have one, even though Simon usually has given him one the previous Tuesday.
Sabrina, an ancient woman who is missing several front teeth, lives across from the Cathedral of St. John the Divine. Unable to cross the avenue to reach the van, she grips her shopping cart and yells, 'I HONGRY!'' A food bag is brought to her. 'HELLO TO EVERYBODY!'' she yells to Simon.
At the Harlem Hospital stop, the alpha in line is a natty and pushy woman known (although she is Chinese) as Mrs. Gotti, who is apt to collect her bag of food, then disguise herself with a change of coat or scarf and get back in line.
The Accountant is a 40ish man at the Central Park stop in a bike helmet and reflective vest. He says he's a CPA but has been unable to find work for three years. Whenever they meet, Simon jokes, 'I hope I never see you again.'' But he always does.
7:55 P.M.: West End Ave. and 86th Street, outside the Church of St. Paul and St. Andrew
Simon manages his route as carefully as his investments.
He's learned to save time by having a few bags of food pre-assembled for stragglers; to have one crewmember chat up the line, thus making the process more personal; to give these people with so few choices at least one, even if it's just what color socks - white, black or gray.
He's learned not to schedule too many volunteers, because everyone wants to have something to do, nor too few, because you never know what can happen.
And he's learned that if something does happen, he can count on the homeless. Once, he lost the van keys outside St. John the Divine. A man in line darted off and came back minutes later with a flashlight. The keys were found.
Simon knows where to buy hot dogs if he's running short of food; when on the route to start offering people two soups, and thus avoid having leftovers; and that candy is always welcome, even if bought on sale after Halloween.
He knows how to defuse situations with chatter and distractions; in six years, he's been in the middle of only one fight, and that was on the Bronx route on Cinco de Mayo. Vanessa Greco, the Bronx driver, says Simon came close to getting laid out.
8:10 P.M.: Amsterdam Ave. and 112th St., outside St. John the Divine
Simon feels intimately familiar with his business clients. But there's so much he doesn't know about the homeless, so much he can't ask because he doesn't want to intrude: How did you get here? What's keeping you? Where do you sleep?
Why does Coat Man always need a coat? Why does The Accountant want only oranges and milk? Where is Mrs. Gotti, whom he hasn't seen in weeks? Why does the shy woman at the 51 st Street stop have a parrot on her shoulder, and why does the parrot not squawk?
8:45 P.M.: Lenox Avenue and 136th Street outside Harlem Hospital
The city says it tries to shelter the homeless without making it an appealing long-term solution. Simon's stated goal is different: 'to make their experience as enjoyable as possible.''
He tries simply to give the homeless what they want, as reflected by what they take and how fast they take it.
While he and his wife were on vacation in Las Vegas, he snagged an embarrassingly large supply of small cereal boxes from the breakfast buffet at The Bellagio, where they were staying. He brought them back in his suitcase for the homeless, whom he says snapped them up.
He lives to move such inventory. He says things such as 'I love underwear. If you're homeless and can't do laundry, you need lots of underwear.''
He delights in their acceptance of his offerings, proving that, as Mother Teresa told her volunteers, the poor are serving you as much as you are serving them.
9:10 P.M.: E. 57th Street and Central Park
Why does he do it? Not, he says, because of religion, guilt or image. It's because he's grateful.
He grew up in Binghamton, N.Y., an indifferent student who attended three colleges before graduating from Buffalo State. When he got to Wall Street, he stumbled onto a mentor who covered for him and promoted him.
'I ask myself, 'How did I get so lucky to have the job I have, when I could have been nothing?' I look at my two kids and think, 'I've won the Lotto.' ''
On the route, he loses sense of time and trouble, whether the market is up or down. He never feels like checking his Blackberry. And it's nice to be appreciated - not always the case in a city where a client might order a $100 appetizer at a restaurant, knowing he's not paying, and not even bother to e-mail thanks.
'In three hours,'' Simon says, 'what's better to do than this?''
9:30 P.M.: Madison Ave. and 55th Street, outside the Sony Building atrium
Simon finds the most frequent request he hears on his route the most troubling: 'Can you help me get a job?'' He can't, not when Ivy Leaguers are looking without success.
'The problem with this,'' he says, referring to the van, 'is we're not doing anything to break the cycle.''
But he will try to get these people through another night on the street. Besides the usual fare, he will hand out warm home-made Christmas cookies, and even more clothes than usual.
O. Henry, a Yuletide chronicler greater even than Clement Clarke Moore, wrote, 'The poorer you are, the more Christmas does for you.' Tuesday night, Isaac Simon will set out to confirm that observation. He hopes it will be a light night; he knows it will be a sad one. Yet he will love every minute.
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