Bernie Sanders was "really disappointed," Jonathan Leopold remembers, when the then-mayor of Burlington learned that his trusted city treasurer was no socialist.
"Socialism is a great idea, Bernie," Leopold says he told Sanders in the early days of Burlington's progressive era. "But it just doesn't work in practice."
A combination of idealism and pragmatism has long characterized Leopold's approach to governance. And 17 years after the bow-tied Vermont WASP from Buffalo, New York, and the wooly-haired Brooklyn Jew ended their triumphant run as the Odd Couple of Burlington politics, he's back - in the job he held previously for eight years.
Unlike the last time around, though, Leopold is no longer viewed as playing a supporting role in the City Hall show, but as the star. Many political insiders suggest it's Leopold who really runs the city, with Kiss as his understudy.
"There's a broad consensus that Jonathan is the guy who's in charge," comments City Council President Kurt Wright, a Republican first elected to represent the New North End in 1995. "The mayor makes the final decisions, I'm sure, but it seems like Jonathan runs the day-to-day operations while Bob stumbles in and out of controversies."
Many Democrats, and even some Progressives, discreetly second Wright's review of the Leopold-Kiss partnership. Joan Shannon, for example, a Democrat representing Ward 5 on the City Council, agrees that Leopold appears to be the dominant of the two.
Not everyone is OK with that. But of more than half-a-dozen sources who were in some respects critical of Leopold's performance, only a couple were willing to say so on the record. Political relationships tend to be overlapping and long-lasting in a city as small as Burlington, which results in a reluctance to name names.
One well-known figure, requesting anonymity because of his ties to both of the principals, observed: "Jonathan's running the city but no one elected him."
Another well-placed official, who agreed to be identified only as a member of the administration of former Mayor Peter Clavelle, sees a certain parallel between the Kiss and Bush teams. In an email message, this source likens the two administrations "not in terms of moral equivalency but in behavior and style - a weak, perhaps ill-suited leader surrounded by zealots who skillfully manage the release of information while claiming openness and operating with scant regard to the human element of governance."
Leopold and Kiss jointly deny that's how things are, although each acknowledges that the mayor looks to Leopold for guidance on financial issues.
"Bob Kiss is very different in style than a lot of executives I've worked under," Leopold says of his putative boss, a politician who still maintains an almost-invisible public profile a year after winning office. "He's very bright," Leopold adds in regard to Kiss. "He's slow in making judgments, very open-minded and respectful that he's on a learning curve."
Kiss, for his part, suggests that "those questions of style are only questions of style." Pols and pundits who see him as his treasurer's understudy "don't understand how government works," Kiss continues. "The mayor is the CEO. Jonathan's not going to do anything I disapprove of. We work together, and I do have a good understanding of the budget."
The city's $219 million ledger holds secrets that only characters with the fiscal acumen of Dickens' Dombey are able to unlock. Leopold knows his way around all the crannies of Burlington's budget, and he's equally well acquainted with the obscurities of the $120 million city employees' retirement fund. He's been burrowing into both documents during the past year, unearthing solutions to what he says were the "daunting" financial problems the Kiss administration inherited from seven-term mayor Peter Clavelle.
Having worked pre- and post-Sanders as an investment manager and financial consultant, Leopold loves what he's doing and is widely regarded, even by his political enemies, as very adept.
But in a recent pair of interviews in his corner office on the second floor of City Hall, the 57-year-old numbers maven insisted he sees budgetary expertise as only a means toward achieving higher ideals.
Money powers government at every level, Leopold points out. Understanding its mechanics in the public realm enables progressive-minded politicians to translate windy rhetoric into concrete programs that produce tangible improvements in real people's lives, he explains.
Leopold says he learned at the outset of his career that "if you want to understand how government works, you have to follow the money." His mentor in this matter was Doris Fraser, whom Leopold describes as a "brilliant" financial analyst who helped revamp Massachusetts state government in the early 1970s. At the time, Leopold had just graduated from the University of Vermont, and was working as a legislative staffer. His job was to study the recently enacted federal revenue-sharing law; more than three decades later, he still - without prompting - identifies is as PL 92-512.
Equally formative in his political development, Leopold notes, was the eulogy Sen. Edward Kennedy delivered in June 1968 for his slain brother, Robert. Leopold recalls Teddy closing with the quote most closely associated with Bobby: "Some men see things as they are and say, 'Why?' I dream things that never were and say, 'Why not?'"
Those were words that shaped his life, Leopold says. "For me, the response was to get involved in government and to make a difference in that way."
Today, he's applying his skills to the challenge of preserving the principles and the programs that have transformed Burlington during the past 25 years. Leopold was there at the dawn of the Sanderista revolution, flush with the thrill of pioneering progressive municipal governance in America. And although that thrill is gone, he's back at the center of the action as a new Progressive mayor strives, in Kiss' own words, to "keep balancing budgets while putting people first."
Leopold is careful not to criticize either Clavelle or Brendan Keleher, his predecessor as treasurer. Both the city budget and the employees' retirement fund were in shaky shape when he and Kiss took over, Leopold does say, adding that the Clavelle administration recognized the problems - if not their full dimensions - and sought to address them.
Leopold describes the situation that awaited the Kiss team in this way: "A retirement system in serious trouble, a budget in serious trouble, four union contracts not settled and a grand list that wasn't growing. It was a fiscal version of a perfect storm."
Leopold adds that during last year's mayoral campaign he told Kiss, half-jokingly, that given the city's financial condition, defeat wouldn't be such a bad outcome. "I said, 'If you do lose this race, you won't regret it,'" Leopold recalls.
He notes, however, that Clavelle did respond effectively to the city's budget gap by winning approval for a local sales tax that prevented the shortfalls from reaching crisis stage. "Peter Clavelle doesn't get full credit for seeing things through," Leopold says. "A lot of mayors might have walked away and said, 'It's not my problem anymore.'" But even after the 2006 Burlington mayoral election, he adds, "Peter was in Montpelier to lobby for the charter change that permitted the sales-and-use tax to take effect."
Neither Clavelle nor Keleher would comment for this story. But sources who are close to both - and do not want to have their names associated with criticisms of the current treasurer - suggest that Leopold is overdramatizing the budget issues he inherited while characteristically presenting himself as a shining savior.
One former city official cites the example of Leopold claiming credit for restoring balance to Burlington's budget, but failing to note that an unexpected infusion of revenues from the city's electric department helped to make that possible.
However, even some defenders of the Clavelle-Keleher record do acknowledge that the City's retirement fund was heading toward difficulties in meeting its fiduciary obligations.
And Leopold wins high praise from financial experts for his efforts to save money by reforming the fund's management and to goose the rate of return on the fund's investments.
"Jonathan is adroit at making creative proposals and challenging the board to make sensible decisions," says Donald Horenstein, a member of the Burlington Employees' Retirement System board. "He's been able to bring people together regardless of whether they have a sophisticated financial background. My sense is we've accomplished more since Jonathan joined the board in 2006 than in the previous three years that I've been serving," adds Horenstein, a retired Wall Street investment analyst.
Karen Paul, who started her own money-management business in 1988 and sold it last year to Key Bank, agrees that Leopold has "a desire to find creative solutions to the retirement system's challenges." A member of the city's pension task force, Paul expresses admiration for Leopold's approach, which, she says, "isn't to say we'll raise taxes or give employees less benefits. He's also not looking for a Band-Aid but for a long-term fix."
Others are less laudatory of Leopold, whose style they see as disingenuous. Both he and Kiss put emphasis on inclusiveness. The administration has expanded citizen advisory roles on city financial matters, saying they seek recommendations from all parts of Burlington's body politic.
But that's just a ruse on Leopold's part, charges a left-leaning former city councilor. "Jonathan's not a team builder," says this figure, who declines to be identified because of his continuing ties to City Hall. "He has some difficulties listening to people who might have ideas different from his own. And I'm not sure Jonathan has the ability to show people they're a respected and important part of Burlington's government team." This former councilor says some city employees have left meetings with Leopold in tears "because he berated them and belittled them."
This inference of arrogance is echoed by many of Leopold's critics. But in both recent interviews, the treasurer and chief administrative officer came across as more self-effacing than self-aggrandizing. His enemies' rejoinder, however, is that Leopold is simply skilled at gulling credulous reporters.
For his part, Leopold does take credit for what he says is recent progress in devising sustainable ways to keep the city's promises to future municipal retirees. To illustrate some of the intricacies of his strategy, Leopold sketches a graph on a dry-erase board in his office. It's a professorial moment. But he doesn't lecture so much as explain.
Leopold has been in the public arena long enough to develop political finesse and media-spinning skills to complement his fiscal wizardry. He says he learned from Sanders to rely on unconventional wisdom in order to prove that "you can have a government that's progressive and that also follows good business practices."
Sanders was constantly urging his appointees to be imaginative in carrying out a progressive agenda, Leopold says. His own role as chief budgeteer became crucial as the mayor struggled in the early 1980s to implement his program despite hostility on the part of Burlington's Democratic old guard. Its members had retained control over the city's still-powerful commissions and were frustrating the vanguard's efforts to introduce a new order.
The Sanderistas wriggled out of that death grip by making the budget a more autonomous instrument, Leopold relates. As a result of reforms they introduced in the city's accounting procedures, for example, Sanders and Leopold uncovered a $1.9 million budget surplus. About $200,000 of that sum was used to seed the Burlington Community Land Trust, itself an innovative response to the perennial shortage of safe and affordable housing. Two years after its launch, the land trust won a United Nations award as a leading international housing initiative, Leopold points out.
He's just as eager to discuss the ways Burlington maneuvered through the esoterica of sewage-treatment-plant funding during the Reagan administration. Let's just say the city devised a financing method that, according to Leopold, became a national model for minimizing the local cost of water-pollution control.
When Sanders judged his time to be up at City Hall, Leopold was widely viewed as the heir apparent. But Clavelle, then director of the city's Community and Economic Development Office, made clear that he intended to run for mayor in 1989. Some veterans of Burlington mayoral campaigns say that Leopold resented Clavelle's intervention and that Clavelle, a self-described Winooski river rat, disliked Leopold's patrician manner. Since then, the two have not exactly been the best of buddies.
But Leopold says he tentatively offered himself as a mayoral candidate in late 1988, only as a tactical maneuver intended to leave the way clear should Sanders change his mind and decide to seek a fifth term. The prospect of holding a powerful elected office "has never appealed to me," Leopold says now. Besides, by 1989 he was exhausted from having worked up to 80 hours a week for the previous eight years, Leopold adds. Plus, "my kids were still young then. I didn't want to keep living that way."
Leopold's living "that way" again. His old job, to which he agreed to return, remains all-consuming.
Leopold worked hard to get Kiss elected, too, even taking part in what some campaign pros regard as the humiliating practice of waving signs alongside busy streets. Leopold supported the former director of the Champlain Valley Office of Economic Opportunity because, he explains, "I believed very strongly his management experience with CVOEO was much more appropriate a quality for the next mayor."
Again, Leopold takes pains not to criticize a key political player - in this case, State Sen. Hinda Miller, the Democrat who lost a mayoral race that many Burlingtonians were sure she would win.
Leopold wasn't among them. "I thought people were underestimating Progressives' chances of winning," he says. "I always believed a good Progressive candidate could win. And Bob Kiss was a good candidate."
Leopold insists he wasn't angling for his current job when he went to work for the Kiss camp. He had been spending two weeks a month in the Bahamas helping his son with a diving-business venture, and was not eager to loosen that family tie or to spend entire winter months in northern Vermont. But when Kiss offered him the post, Leopold accepted.
Both Mayor Clavelle and Chief Administrative Officer Keleher would be leaving at roughly the same time after having acquired considerable skill in their respective posts, Leopold says he reasoned at the time. "There would be a new mayor coming in with no direct experience," he says he further reflected. "And I thought I could bring some experience in regard to what needed to be done."
Which returns the narrative to its opening question: Is Leopold actually running the city while Kiss serves in a figurehead capacity?
Here's more from Kurt Wright: "With Peter Clavelle, regardless of our political differences, I always knew he was the mayor, he was the guy, he was the leader. It's not like that with Bob."
Kiss and Leopold will get the last words, however.
"People may well mistake Bob's quiet style for not being engaged," Leopold says. "That's not accurate; he's highly engaged."
Kiss points out, "I'm not Peter. I'm not Bernie. I do things my own way. In the legislature, I got results even though I wasn't outspoken. I'm doing the same as mayor."
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