Lenny Kaplan, an elite name on the Baltimore restaurant scene, is not one to see the glass half empty. Of course, he might wonder if the glass could be a tad more polished, or served quicker, or filled exactly to the level it's always been filled, or offered in better lighting, or on a tablecloth spread with greater precision, or generally represent absolutely his quite well-defined notion of what the customer wants in a glass.

This is something of what makes Lenny, Lenny - a man noted both for setting high standards and occasionally chewing heads off the help. Perhaps this striving lies beneath the wistfulness Kaplan conveys one evening in his waning days as owner of the Polo Grill at the Inn at the Colonnade. After finishing a plate of rockfish with lobster sauce and steamed spinach on the side, he says he has relished his four decades in the restaurant business, has enjoyed feelings of success.

And yet.

"I have been lucky to be relatively successful," says Kaplan. And he repeats: "relatively."

On New Year's Eve, he'll do it one last time. The trim 65-year-old will ride the elevator down from the ninth-floor apartment he shares with his wife and restaurant co-host, Gail. He'll turn out in one dapper outfit or another to work the floor with that megawatt smile and his acute sense of doings around him that made him a successful basketball point guard in high school and college. It's the point guard who sets the play, ensures everyone's where they're supposed to be, anticipates next moves.

So it goes for the "front-of-the-house man," as they say in restaurant talk.

If he's not filling in for the chef in an emergency, find him day and night working the floor or sitting at the Polo Grill bar, first stool facing the restaurant, where he eyes the dining room like an air traffic controller watching radar. If by chance he takes a meal with friends, they can depend on many conversational interruptions as Kaplan prods his staff.

"In the middle, he'll say, 'Table 19 needs water,' 'Table 12 is waiting for their check,' " says Julius Zulver, who has known the Kaplans for about 30 years.

"It's the details," says Kaplan, who opened the Polo Grill in 1990. "Whatever they are. I don't think I'm picayune. I'm picky about the same details."

Forty-three years, several successes, one conspicuous failure at Lennys Chop House - countless details. Now it comes time for Kaplan, who once took over the renowned Pimlico Hotel restaurant from his father-in-law, to turn things over to his son-in-law. Rob Freeman, 37, who has been general manager since 1997, assumes ownership of the Polo Grill on Wednesday.

In months, the Polo Grill will be no more. While a few signature dishes may remain - fried lobster tail, for instance - Freeman says in the spring, he'll unveil a new name, a new lower-priced menu, a new expanded bar with a separate entrance and certain decor changes. Most of the particulars are being withheld until further notice, but clearly the Kaplans will depart their public roles.

Kaplan's exit marks an era ending, if only by virtue of his association with a couple of the city's most popular restaurants: the old Pimlico Hotel on Park Heights Avenue and the Polo Grill. Each in its day emerged as a center of Baltimore sociability and status.

January's "Table Scraps" column in Restaurant Digest, a regional food service industry magazine, notes Kaplan's departure, calling the Pimlico Hotel "a landmark eatery if ever there was one," and referring to the Polo Grill as "the place to be seen."

A rock's throw from the Johns Hopkins University's Homewood campus, the Polo Grill belongs in the American scrapbook alongside advertisements by Ralph Lauren, a man born Lifshitz who also understood "WASP" as an appealing brand identity. The antique-look prints on the walls showing white men playing polo and golf, the pool-table colored wall fabric, the cherry wood paneling - it all suggests the sort of patrician club that might have barred a Kaplan or Lifshitz in less enlightened days. Say, around the time Gail's father, Leon Shavitz, and Nathan Herr opened Nates & Leon's delicatessen on North Avenue in the 1930s.

Things have come along. At the Polo Grill now, there are little signs on each table announcing the end of the Kaplan era, summarizing the family restaurant history and suggesting a cultural story: "From Knishes to Coffey Salads to Fried Lobster."

The Pimlico - where waitress Claudia Coffey created the eponymous melange of tomatoes, hard-boiled eggs, chopped iceberg lettuce, onion, Parmesan cheese and seasonings - was a child of 1950s American eating, with notable innovations by Shavitz. The menu thick as a U.S. road atlas included everything from chops to chow mein. Kaplan tells how Shavitz added Chinese food to the menu, but not before he went up to New York and hired a Chinese chef to assure authenticity.

Soon after Kaplan married his University of Alabama sweetHeart, Gail Shavitz, in August 1959, her father offered him a job at the Pimlico. A newly minted bachelor of science in business administration, Kaplan had waited tables in the Catskill Mountains as a kid but otherwise knew little about restaurants.

"My father-in-law said, 'I don't want you to do anything for a year. I want you to walk and watch,' " says Kaplan.

With crowds massing to 300 on Preakness day and New Year's Eve, and a staff over 150 strong, there was enough to watch. Kaplan watched the action and watched Shavitz watching. Shavitz was the gregarious, roundish man often seen standing by the kitchen of the Pimlico with a towel draped over his arm watching each order go out, wiping clean the rims of the plates. He would fuss with the garnish, sending plates back for a makeover if the food was not arranged just so.

Thus Kaplan found his calling in the restaurant business, a haven for compulsives and hardly famous for the gentle touch of management by consensus.

Kim Acton, who owns the Pazza Luna restaurant in Locust Point, can't say enough flattering things about Kaplan, to whom she is grateful for her first job in the restaurant business - as a part-time hostess at the Pimlico. While she talks about Kaplan with reverence, as a great teacher and friend, at the same time she says, "there were times he made me mad, there were times he made me cry. There were times I walked out on my shift" in anger.

The staff member who slipped up on a detail or two would be subject to the eruption of Mount Kaplan, often in public view, says Acton.

"He'd simply rip his glasses off his face and scream in front of guests," she says. "The guests, I'm sure, were appalled by it."

Mark that up to expectations, says Kaplan, not least his own expectations of himself.

He says he's probably more mellow now than in years past, but no less forgiving of what he considers poor performance, anything that "might embarrass me or make me look bad to my guests. ... Whatever transpires ultimately reflects on me. Our guests have put their confidence in me. If we don't perform, then I've let them down."

Harold Marmulstein, the Polo Grill's first executive chef and creator of the famous fried lobster tail, knows the complaints about Kaplan but says he considered the boss a kindred spirit and they got along well.

"I'm a very strong personality, and I know what I'm doing," says Marmulstein, now executive chef at Dick & Harry's in Atlanta. "If you're not a strong personality, if you're not aggressive enough, he'll run up and down your back."

For all his bluntness, Kaplan left former chef Stephen Bohlman feeling he'd been misled. Bohlman, who had worked with Kaplan in the 1990s, left a job early this year to become the Polo Grill's executive chef, thinking he had a future with the business. In the fall, Bohlman learned accidentally that Freeman was making plans without him.

"I felt betrayed," says Bohlman, who quit in October when he was told he would not have a job in the new restaurant.

Kaplan and Freeman have only high praise for Bohlman's work, saying the new restaurant demanded new leadership in the kitchen.

Marmulstein and Jonathan Charmatz, who had met at the Culinary Institute of America, were the chef and sous chef team that put the Polo Grill on the map when the place opened in March 1990. Reviewers were dazzled by rockfish with chanterelles, penne pasta with chicken, an appetizer of crisp soft-shell crab "cunningly seasoned," said Baltimore magazine, with dill, coarse mustard and horseradish.

Pretty soon you needed a few weeks notice to get a weekend reservation. Zagat raved, as did the Mobil Travel Guide. Leon Shavitz's son-in-law - who had by then also come and gone in the early 1980s as manager of the John Eager Howard Room and the Owl Bar at the Belvedere Hotel - had struck out on his own in splendid fashion.

And yet.

It's as if there were some restaurant equivalent of a biological clock. The Polo Grill thrived through its first year, by which time about 90 percent of American restaurants fail, says John Antun, founding director of the National Restaurant Institute. Trouble began as the restaurant approached its 10th year, an anniversary that 99 percent of restaurants do not live to celebrate, says Antun.

In the last three years, Kaplan has gone through executive chefs the way New York Yankees owner George Steinbrenner used to go through field managers. They just couldn't find the right combination, he says. As Freeman recollects, seven chefs have come and gone since 1999.

Crowds were off from the early years, especially in the last 12 months, but it's hard to say if that was due to the upheaval in the kitchen, competition from new restaurants or the sort of cooling effect expected in any restaurant's life.

Baltimore magazine this fall noted that "the tumult" in the kitchen did not show in the quality of the food. Ironically enough, the magazine's October issue hailed Chef Bohlman's re-appearance as a return to the good old days.

Just as the turmoil was beginning at the Polo Grill, Kaplan experienced his first big business setback. In April, 1999, Lennys Chop House at the Harbor Inn Pier 5 closed after only 15 months in business. Bigger than the Polo Grill, the classic American steak house was to be the crowning achievement of Kaplan's restaurant life.

"Lennys Chop House was my end game, my ultimate goal," says Kaplan. Unlike the Polo Grill, which is obligated to provided breakfast, lunch and room service for Colonnade guests and condo owners, the Chop House was open only for dinner. With its giant gilt-edged mirrors and rosy wood trim, the Chop House was clearly meant to be a showcase.

Kaplan put the best face on the closing, saying at the time that he simply could not agree on lease terms with the Pier 5 partnership. The actuality seems somewhat more complicated, as Kaplan wound up being sued by the Pier 5 partnership for nonpayment of rent. This summer, he agreed to pay a $46,000 settlement.

Kaplan's answer to the suit claimed that the Pier 5 partnership, through member Michael Lasky, came up $350,000 short of its promised $1.6 million investment. The Kaplans said they wound up sinking more of their own money into the deal, putting the restaurant at a disadvantage.

While he has only good things to say about Kaplan, Lasky says the partnership's investment had nothing to do with the restaurant's failure.

"He had the customers," says Lasky, founder of the now defunct Psychic Friends Network who declared bankruptcy in 1998. "He had all the business, why did he lose it?"

Says Kaplan: "It was just a combination of things."

Perhaps construction around President Street discouraged customers. Perhaps the valet parking was a problem. Perhaps the place was hard to find. Kaplan is not inclined now to blame anyone else: "It was my responsibility to make it work, and it didn't."

He acknowledges that the Chop House failure may have influenced his decision to leave the Polo Grill.

"Did it affect me psychologically? Certainly it did," says Kaplan. "It certainly said to me: 'How long do you want to continue to do this?' "

Kaplan, father of three, grandfather of six, will continue working as a restaurant consultant and may have a bit more time for golf, poker and running up to Manhattan to see opera. If pressed to give an operatic preference - "there's not much in opera I don't enjoy" - he mentions Giuseppe Verdi and Richard Wagner.

He's sitting at a table near the center of the Polo Grill, a venture that was born in his imagination when he visited Stars restaurant in San Francisco in the late 1980s. For openers it was just what he envisioned. The conclusion seems somewhat less so.

"It may not have been on the terms I would have liked," says Kaplan.

The exact meaning of that is unclear, as the master of details withholds details about this. Perhaps he might have made more money, he says. Perhaps the glass might have been more perfect yet. He's not dismissing the success he's had, or the good times or the personal satisfaction. Yet, he's talking about places like Tio Pepe and the Prime Rib, restaurants that year after year "found the magic bullet that I think are necessary: consistent food, good service, value."

On New Year's Eve of all nights, prone as it is to blend longing and expectation, Kaplan will make the show one last time. There'll be hats and noisemakers and a full house, much as it was when the Polo Grill was packed every weekend.

"It's a wonderful, vibrant feeling," says Kaplan. "I have loved every second of it."