The sky seems ready to dump a load of snow, and it’s so cold that even the tree looks freezing. The coatless Jennings, who hates to be late and who checks his Movado watch with the same frequency that most people blink, hurries over to the group.

No reporters have come out to the tree planting, a fact that the mayor notes with disappointment before his voice reaches the others.

Not to worry: He still works the little gathering like it’s the last hour of the campaign before Primary Day: a few jests, a couple of friendly punches on the arm, a joking exchange with a friend about the quality of his overcoat.

“Amore? Only people with money can afford that guy,” Jennings says, laughing and reaching to turn the man’s lapel inside out for a closer look at the tailor’s label.

This is the side of Jerry Jennings that the public sees: the joking, the joshing, the habit of addressing everyone from congressmen to cleaning ladies with the moniker “kiddo.”

But after eight years in office, the Honorable Gerald D. Jennings has developed a reputation for another side that too many people in Albany who have crossed him say they have seen—a side that wields political power to the point of making people afraid. Afraid for their jobs, afraid for their reputations, and, some say, afraid for their families.

He is neither cerebral, as Erastus Corning was often described, nor remote, a term that even some of Thomas Whalen’s friends used to characterize Albany’s last mayor. But anybody who thinks Jennings isn’t smart has never taken him on in a public clash.

The mayor had no opposition to speak of in his last race, none has appeared on the horizon since then, and still most people pick their public remarks about Jennings very carefully. There may be some unhappy apparatchiks in Albany politics, but there’s no sign that anybody’s about to start a revolution.

Ask many politicians deep into their time in office to reflect on the things they wish they had done differently, and their answers will likely focus on humbling lessons learned the hard way. Long tenures carry the risk of stumbling, but they can also humanize their subjects. Even Rudy Giuliani had enough sobering moments in his final months in office to make him look more like a lonely guy strapped with the world’s toughest job than a peevish bully picking on art museums.

Ask Jerry Jennings what he wishes he’d done differently, and his answer has nothing to do with somber introspection and everything to do with personal power—a quality he views as a natural outgrowth of his job.

“I don’t think I realized the amount of influence you can have as mayor of the capital city on state government leaders,” the mayor says, without missing a beat.

Influence is fine. Most people don’t have a problem with influence. It’s the other stuff they worry about—the stories of threats, implied or stated, of yanked contracts because someone crossed City Hall the wrong way, of petty shows of power that would be almost funny if they weren’t true.

If you can’t get the mayor to take your phone calls, if he’s ticked off at you and has temporarily banished you (and “temporarily” sometimes means years), then call his radio talk show on Friday mornings.

Unless you start swearing at him or otherwise violating FCC rules, he pretty much has to listen to you on the air, however much he may roll his eyes or circle his finger around his ear in the privacy of his City Hall studio while doing so.

It’s not a bad deal: The mayor gets an hour to promote himself and all that he’s done lately for the city, and the callers get Jerry Jennings—not the world’s most patient person—as a captive audience. Paul Webster, who ran against the mayor’s choice for school board last fall and won, takes wicked delight in occasionally popping up unexpectedly as a caller to the show.

Jennings has been doing his radio show almost steadily since 1994, first on what was then known as WQBK-AM (1300 AM) and now on WROW (590 AM). The show goes off the air during his campaigns. He insists that the callers are not screened or prepped in advance (“You kidding me?” he replied when asked) and says he pretty much wings it through predictable questions and complaints.

This is Jennings in his element. He’s dealing with a largely sympathetic and complimentary audience, and he comes off as benevolent and attentive, dispensing promises over the air that city agencies will be dispatched that same day to correct a problem. And usually they are.

He is masterful at this, at the art of reaching people and making them feel that he really cares. Those who have watched Jerry Jennings’ growth in office say this skill makes it all the more difficult to understand why the mayor reacts to reasonable opposition, much less open dissent, with such an intensely personal response.

“There are enough good things, enough good ideas that Jerry Jennings brings to the table that it always surprises me that he is so reluctant to tolerate any disagreement,” says Shawn Morris, alderwoman for Albany’s 7th Ward, who came on in 1994, the first year of the Jennings administration. “Any questions, and you get accused of being negative and shot down and shut out of the process. There’s no reason for it.”

Jennings says his critics should consider his record.

“One thing you learn in this job is you better have thick skin,” the mayor says. “All I want people to do is look at what I’ve done as mayor. I can’t please everyone all the time, and I learned that early on in this game.”

Albany attorney Jerry Weiss, a Jennings political ally, is suspicious of personal attacks on the mayor’s character, especially in view of Jennings’ record.

“In a city of 100,000 people, there are always going to be people who are dissatisfied,” Weiss says. “Things can always be better. But when people cast personal stones and talk about personalities, I tend to doubt their complaints. I then look beyond the complaint and ask myself, ‘Does this person have an agenda?’ And I usually find that someone willing to make a personal complaint is someone with an agenda.”

Among the good things that Morris—and almost anyone else—would list to Jennings’ credit: He struck a deal with the state that guarantees hundreds of millions of dollars to the city as payments in lieu of taxes for Empire State Plaza over the next 30 years. He has helped make Albany’s downtown far livelier, backing the construction of several new buildings. He has connected the riverfront to the city; a long-awaited pedestrian walkway linking downtown to the river is expected to open in June.

The mayor has backed a number of civic projects, such as the Citizens’ Police Review Board and the revitalization of Grand Street, that wouldn’t have gotten out of the gate without his support. He has forged solid relationships with minority leaders in the city, too. Jestin Williams, a longtime Arbor Hill activist and committee member in the 3rd Ward, praises Jennings’ accessibility and genuine concern for the city’s poorer residents, a trait that Williams traces to Jennings’ days on the Common Council.

Given these achievements, no one’s trying to shoot down Jennings’ reputation. It’s difficult to make a case against him on what he’s done for Albany. So why the spiteful streak?

It’s not like he doesn’t know what it feels like to be punished. This is the guy who was so shut out of his own party as a Common Council member in 1989 (for opposing a Pine Bush development issue backed by Democratic Party regulars) that he had to conduct a write-in campaign—a desperate measure, by any standard—to retain his own council seat.

You’d think that might give him a better understanding of people who try to buck the system (which in Albany means bucking Jerry himself), but the mayor shows little tolerance for such antics, as he demonstrated when Albany comptroller Nancy Burton quit in early 2001.

Burton had a long history as a political independent, and was never exactly the mayor’s philosophical kindred spirit. Burton joined the staff of state Comptroller H. Carl McCall after quitting, and declined to speak for this story, saying that she had moved on and didn’t want to revisit the past. But before she left City Hall, Burton said that Jennings and his ally, city Treasurer Betty Barnette, engaged in a systematic effort to isolate her to the point that she could no longer function as comptroller because she no longer had access to essential information.

Morris was one of the few people approached who was willing to discuss, however diplomatically, the mayor’s penchant for payback. More than a half-dozen other people queried about this side of Jerry Jennings declined to comment, with several stating a concern about retribution.

The mayor must know his own reputation for payback; he’s been heard making jokes about it. At a public meeting last winter on his proposal to move an $800,000 federal transportation grant from Lark Street to New Scotland Avenue—a proposal that triggered a storm of protest by Center Square residents—one resident stood to ask a tough question of the mayor. Before he answered, Jennings turned to Public Safety Commissioner Jack Nielsen, seated at the table with him, and said, “Jack, follow him home.”

Everyone laughed, but in Albany, that kind of joke isn’t always funny.

When he’s not being jocular at public meetings, the mayor adamantly rejects the suggestion that people don’t want to get on his bad side.

“There are some people out there who do not like my style,” he says. “I’m aggressive. I’m impatient. I like to see things accomplished. I don’t have time, number one, nor is it my style, to be vindictive. I don’t have a problem letting people know I have a problem with their position.”

That may be the only point on which Jerry Jennings and Elda Abate, owner of Elda’s restaurant on Lark Street, will ever agree.

In 2000, Abate bought the crumbling but historic St. Joseph’s Church in Arbor Hill for $1 from the Roman Catholic Diocese. The church is walking distance from a number of Albany nightspots that have opened under a renewed focus on downtown during the Jennings years—the Big House Brewing Co. and Jillian’s, on North Pearl Street, and an enhanced McGeary’s Restaurant on Clinton Square. Abate and her husband Mario envisioned the renovated church as a reception site for weddings and private parties that would fit in well with the downtown scene.

Abate is now fighting more than $70,000 in city fines for safety violations at the site, and has accused the city of using the fines as a backhanded effort to seize the church. Last fall, the city also shut down Bliss Lounge, a lounge/nightspot that Abate opened adjacent to her Lark Street restaurant, saying that she was operating it without a permit.

In a recent interview, Abate accused Public Safety Commissioner Nielsen of offering a quid pro quo: Her lounge could stay open if she ceded the church to the city.

“‘This administration wants St. Joseph’s,’ ” Abate says that Nielsen told her. “ ‘If you don’t give up St. Joseph Church, you’re going to be shut down.’ I said, ‘What do you mean, this administration? Do you mean the mayor?’ And he said, ‘Yes.’ ”

Nielsen denies the accusation, saying he never stated or implied that a deal could be struck. He insists all city agencies treated Abate properly.

“I’m going to be polite about this: She skews things to sound like other than they were,” Nielsen says. “I was very clear to tell her we have two issues here. My responsibility is to the citizens here. In both cases, I had citizen groups who came forward and had concerns about what she was doing. As for the church—we never wanted the church. By ‘we’ I mean the city.”

But Abate remains convinced that Jennings has applied undue pressure.

“We are going out of our mind to find out why this guy is doing this to us,” she says. “He’s a very powerful man. People fear him.”

If you’re running for city of fice in Albany and you aren’t on the mayor’s team, you can pretty much count on him putting up a candidate against you to force a primary. The Jennings candidates don’t always win—but maybe winning isn’t the whole point of this exercise.

“It was very intimidating,” says Common Council member Dominick Calsolaro, who was elected last fall after a primary against Kathleen Myers, a 1st Ward committee member who was backed—some said pushed—by Jennings.

Calsolaro had the blessing of the ward’s committee, but he had also been a leader in the neighborhood movement that opposed and then blocked the reconstruction of the Lincoln Park Pool, a Jennings pet project. A neighborhood group called Friends of Lincoln Park pool was created to protect the unique, lake-like structure as part of the city’s historic fabric. They helped postpone the mayor’s proposal to replace the structure with a smaller, modern pool. Then, Myers appeared as a candidate in the 1st Ward, less than two weeks before petitioning for the race started.

“The mayor’s people did all the petition work,” says Calsolaro, who has since worked cooperatively with the Jennings administration on several projects.

There is the argument that rough primaries are only to be expected in a city like Albany, where down-and-dirty politics have been part of the landscape longer than anyone can remember. Given that history, it’s hardly surprising that Jerry Jennings is well-schooled in the art of primaries, says one Albany veteran of ward politics.

“You’re stepping into his arena and spitting in his eye, and what do you expect—‘Well, I thought it would be a real clean process’?” asked the veteran, who spoke on the condition that he not be named. “Well, put down your civics book and get a reality check. A primary is nasty shit. I’ve run some nasty primaries.”

Most politicians schooled in the Albany way of doing things can accept rough and nasty. But one memorable Albany primary raised questions about whether the usual tactics crossed a line that sent a disturbing, even frightening, message.

In 1998, Jennings backed Albany County legislator Gary Domalewicz in a primary against Jack McEneny for McEneny’s state Assembly seat. The move was said to be payback for McEneny, who had run for mayor against Jennings in 1997 and gotten trounced.

In the only part of this story that’s even remotely funny, McEneny likes to tell how the city paved all the streets around his Colonial Avenue neighborhood during the ’97 mayoral campaign, but skipped McEneny’s street and another nearby street that had a bumper crop of “McEneny for Mayor” signs on the front lawns.

In the 1998 Assembly primary, McEneny kept his seat, beating Domalewicz three-to-one in the primary. McEneny’s daughter Rachel managed her father’s Assembly campaign, as she had his mayoral race.

The Domalewicz-McEneny primary then took a weird twist: In the early morning hours after McEneny’s victory, an Albany cop pulled Rachel McEneny over on her way home from an election-night celebration and arrested her on a drunken-driving charge.

The case ended up becoming an embarrassing debacle for both the cops and the prosecutor’s office. McEneny secured a blood-alcohol reading for his daughter through a blood test at a local hospital. The test results suggested that she would have needed a superhuman metabolism to produce the reading that Albany cops said they got on the Breathalyzer test. The court threw out the results, and a jury acquitted Rachel McEneny.

“It’s been three years for Rachel since going through that very traumatic and degrading experience, and since the jury has found her not guilty, and no one has had enough class to offer her an apology,” McEneny said.

McEneny says he has never had any evidence that suggests Jennings was in any way behind Rachel’s arrest. He endorsed Jennings in the mayor’s bid for reelection last year. He talks convincingly about how Jennings has been a good mayor for the city, about how he has responded to many of the problems that McEneny noted in his own campaign. But McEneny has also never forgotten what happened to his daughter, and he says such incidents can have a chilling effect in a city.

“I think there was a climate that would bring about that vindictive action; there was a climate in the city,” he says.

When asked if he thinks that climate still exists, McEneny replies, “I don’t think it matters if it exists, if people think it exists. It’s not necessary that law enforcement will go after your children; it’s necessary that people think you’ll go after their children. Perception.”

Hundreds of people in Albany still think of Mayor Jennings as Mr. Jennings. They’re the children and parents of children who went to Albany High School under him, first during his tenure as a teacher, then as an administrator.

Jennings has been out of the city’s public school system for almost a decade now, but his criticisms of how those schools are run have become one of the most contentious issues of his administration. He wants to appoint a couple of members to the school board, an idea that is not unique to Albany. Buffalo Mayor Tony Masiello has been trying for years to get a special bill through the Legislature that would allow him to have two school-board appointments in his city, but there has been little evidence that the Legislature is going to budge on the request.

Jennings started in the Albany school system in 1970, first at Philip Schuyler High School, then at Albany High as a social studies teacher. His ex-wife, Gracia Chicorelli, was part of a powerful Democratic family; her aunt, Regina Chicorelli, was a longtime member of the Albany School Board. (Jennings’ second wife, Mary Ann Severino, is a secretary at the high school.) The Albany school system was a bastion of political patronage back then—as was just about every other urban school district—but Jennings bristles indignantly at any mention of family connections in his first career. Slogging through night school got him his job, he says, not political pull.

He taught for five and a half years, and then became an assistant housemaster. By all accounts, he was exceptionally popular with parents and students. He ended up as the school’s vice principal, and it could be argued that those years provided formative lessons in the art of building a power base.

“At no point did he ever become the principal of the school, but there was an acknowledgment among the employees that he was one of the most powerful people in the building, if not the most powerful person in the building,” says Bill Ritchie, president of the Albany Public School Teachers’ Association and a guidance counselor at Albany High in the middle years of the Jennings era there.

Neither Superintendent Lonnie Palmer nor school board president Theresa Swidorski would comment on Jennings’ interest in the school system.

Paul Webster, elected to the board last fall, decided to talk, and says the mayor’s interest in seeing the schools improve is understandable. Webster disagrees with Jennings on how that interest should be applied. If the mayor wants to influence the school system, Webster says, he should do so by continuing his laudable record of obtaining state and federal aid for the city, and then channel as much of that aid as he can into reducing Albany’s poverty level.

“I agree with his concerns that the schools must do better, that the schools could be better managed from an administrative and academic standpoint,” Webster says. “Jerry and I just differ on who should have control of the schools. No one wants to deal with the fact that the parent of the average child in the Albany school district is a single minority mom who is living at or below poverty.

“The mayor alone can’t fix the school ills.”

This isn’t the first time Webster and Jennings have disagreed.

In 1994, Webster recalls, his public opposition of the mayor cost him a contract. At the time, Webster was the owner and publisher of the Sojourner Herald, a monthly newspaper geared toward the city’s minority community. At the time, the city regularly published a quarter-page ad in the paper, touting Albany’s home-ownership incentive programs.

Webster joined forces with a group of community activists protesting a proposal backed by Jennings that would have removed $90,000 in community development block grant funds from six community groups, and given the money to the Albany Police Department for use in departmental antipoverty programs.

“We were like, ‘You know, the police department is not an antipoverty group, and it’s not a community-development group,’” Webster recalls. The protest pressured the administration into restoring the funds to the community groups. A month later, the city yanked its regular quarter-page ad from the Sojourner Herald. The ad cost $100 a month, not an inconsequential amount to a small paper, Webster said. Webster has never had any indication that the mayor personally ordered the ad to stop, but he also fully expected that the ad would be the cost of his stance on the block-grant money.

“I considered it a victory,” he says, adding that he gets along fine with the mayor these days.

“You can disagree with the mayor and still work with him, and I think people have to learn that,” Webster says. “And I think the mayor could do a better job working with those who don’t necessarily share his view.”

Bob Berry, who worked as a strategist and media advisor on Jennings’ first mayoral campaign in 1993, gives a harsher assessment. Berry had a falling out with Jennings shortly after Jennings took office in 1994; Berry says the mayor inexplicably cut him off, and later severed ties with several other people who gave him early support.

“The man had so much potential,” Berry said. “I believed in him with my heart and soul. I believed in him as a brother, and to see how many people have been hurt and ignored is difficult. Nobody is willing to stand up to Jerry, because there’s this fear factor. And arrogance will be his downfall.”