The Man Behind the Throne 

The most powerful man in Vermont politics has never held elected office. He’s never sought name recognition or the limelight. And his friends and longtime colleagues insist he doesn’t wield his influence for personal profit.

But, through Democratic and Republican administrations, Harlan Sylvester has had the ear of every one of the state’s chief executives — going all the way back to Gov. Tom Salmon in 1973.

Prominent businesspeople and pols flock to his corner office at Morgan Stanley Smith Barney on Swift Street in South Burlington, a Chittenden County substitute for the governor’s office in Montpelier. As chairman of the Governor’s Council of Economic Advisors — a post Sylvester has held since Gov. Madeleine Kunin was in office — the now 77-year-old personal money manager often sees the state budget before Vermont lawmakers do. Just don’t ask him to confirm, or comment on, his role as the governor’s proxy.

“Harlan never says, ‘I’m talking for the governor.’ He always tells people, ‘I might be seeing the governor’ or ‘I might be talking to the governor,’” says Steve Terry, a former journalist and executive at Green Mountain Power, who calls Sylvester a friend and serves with him on the Governor’s Council of Economic Advisors.

“He is very protective of that relationship with governors,” says Terry. “And, like all people I’ve known who follow the rule in the White House — that you never repeat what the president told you or discussed — as far as I can see, he’s used those rules in Vermont.”

Sylvester’s behind-the-scenes political prowess has earned him the dubious distinction of being part of what many insiders call the “Burlington Bishops” or the “Chittenden County Mafia.” The implication is that to run for statewide office, candidates — Republican and Democrat alike — must first “kiss the ring.”

Others in this esteemed club include former KPMG executive David Coates and insurance exec Luther “Fred” Hackett. While Sylvester and Coates are Democrats, they often support Republicans, such as Gov. Jim Douglas, who are in sync with their business-friendly views. Hackett has always been a Republican and lost a governor’s race in 1972.

Sylvester’s secretive ways have also earned him a long-standing, and perhaps at times unfounded, reputation as a puppet master, the proverbial “man behind the curtain.” The man some insiders call the “Prince of Darkness” declined to be quoted for this story.

“He’s got access to people with real money, and those people with real money will invest in politicians who will protect their interests,” says Garrison Nelson, a University of Vermont political science professor and longtime political observer. “Harlan’s basic goal has always been to keep the tax rates low for his high-end clients, and he’s found congenial Democrats and Republicans to go along with him.”

Sylvester also has a knack for sniffing out winners in multiple primaries and backing the ultimate victor in a statewide contest. This is one reason why pols of all political stripes reach out to him.

Sylvester is supporting Brian Dubie in the governor’s race, but that didn’t stop all the Democrats in the five-way gubernatorial primary — except Racine — from seeking his counsel.

“A lot of politicians will meet with Harlan because, even if you can’t get him on your side, you want to at least neutralize him,” says former Gov. Phil Hoff. “In other words, you just want to make sure he’s not working against you.”

A horse-racing fan, Sylvester knows how to hedge his bets to ensure he earns a little something from the winning jockey. He was said to be “intrigued” by Secretary of State Deb Markowitz in the Democratic primary. But when Peter Shumlin began to surge, he started talking up Shumlin as the Dem to beat.

The result? If Shumlin wins the governor’s race next week, Sylvester won’t be left out in the cold. He and Shumlin already have a relationship. In a carefully worded statement, Shumlin explains, “I don’t comment on private conversations I have, because I’m afraid they wouldn’t have any more private conversations with me.”

Early in his career, Sylvester was one of two regional managers to sit on the national board of the powerful investment firm E.F. Hutton, whose famous advertising slogan was “When E.F. Hutton talks, people listen.”

That slogan easily sums up Sylvester’s role in Vermont politics. No matter who is elected governor next week, one thing is clear: Like his predecessors, he’ll likely be listening to Harlan Sylvester.

From Blue Collar to White Collar

His clients are among the wealthiest people in Vermont, but Sylvester’s own Green Mountain origins are humble.

“He has never forgotten his blue-collar roots, living in St. Albans, and that’s an important aspect of Harlan that most people don’t know,” says U.S. Rep. Peter Welch. “No matter how successful he’s become, that connection remains, and it really infuses his beliefs, which he is more than willing to share with you whether you agree with him or not.”

Sylvester’s first encounter with politics came early — at 12, he served as a legislative page. That meant making the daily drive from St. Albans to Montpelier with two Franklin County lawmakers, one of whom was his Republican father. Harold Sylvester later became a Vermont Supreme Court judge.

“He often credits those rides with helping him understand Vermont politics and shaping his personal philosophy,” says Mark Snelling, the son of former Gov. Richard Snelling and Lt. Gov. Barbara Snelling, and a recent candidate for lieutenant governor himself.

Sylvester’s lifelong love for high school hoops started at Bellows Free Academy-St. Albans, where he was a star player. At the University of Vermont, he joined the jock-filled Kappa Sigma fraternity and played one season on the freshman basketball team.

He studied economics and political science and graduated in December 1959. After a six-month stint in the Vermont National Guard, he spent several years in the reserves.

According to Terry, Sylvester took out a loan to buy his first two business suits and went off to learn the ropes of high finance working for Hartford Insurance Group in Connecticut.

He returned to Vermont to work for Penn Mutual. In 1966, Sylvester took a job with the financial services firm F.I. du Pont managing people’s personal investments. From 1969 to 1998, he managed the office as his New York-based employers came, went and merged. In 2003, Sylvester’s checks came from Salomon Smith Barney. Then it was Smith Barney, which was owned in part by Citigroup. In 2009, Smith Barney merged with Morgan Stanley to become Morgan Stanley Smith Barney.

Sylvester’s political access and financial prowess helped position his company to sell bonds on behalf of the state of Vermont.

His brokerage was the firm of choice during Douglas’ tenure as state treasurer and earned several hundred thousand dollars in commissions selling state bonds that fueled construction, roadwork and other state capital investments. During the tenure of current Treasurer Jeb Spaulding, the commissions have mostly gone to Citigroup, though Smith Barney is often a secondary broker in state bond sales led by Citigroup.

A review of bond sales shows Smith Barney has a strong track record of selling bonds to Vermonters and regional investors, which is considered preferable to offering them to investors from out of state.

“He always spent a lot of time working close to the people who manage the state’s money, but he didn’t directly gain anything from it; he just wanted to make sure he had a seat at the table,” says Art Ristau, who served as Kunin’s secretary of administration. Ristau also worked for governors Salmon and Snelling.

“If there ever was a bond issue on the table for the state or VSAC [Vermont Student Assistance Corporation], he would belly up with a quote,” Ristau says. “He’s very competitive. He loves the action; he loves to be around the power, the money, and the influence.”

Influence Broker

Sylvester has been a bridge between politics and commerce since Gov. Salmon was elected in 1972 — almost 40 years ago.

“He had emerged as an important personality in the Vermont business community, and we had some mutual friends,” says Salmon. “He’s … very much keyed in to trends in the business and investment world, given his calling in life, but he’s also just as much a very astute observer of the political world, and everyone would hope to have him working in their interests.”

It was during Salmon’s tenure that Sylvester earned a spot on the Vermont Racing Commission — a panel he has chaired since the Dean administration. While it currently subsists as an “office” in Rutland with no budget allocation, the commission was once a well-oiled conduit for tickets to the racetrack in Saratoga.

“Harlan is a very bright, engaging person who is incredibly smart and loves politics,” says Kunin, who acknowledges she benefited from Sylvester’s counsel before and after she became Vermont’s first female governor.

“He just feels passionately about certain issues, and it’s important for any administration — Republican or Democrat — to hear those voices,” says Kunin. “It’s even more important for Democrats, who are always under suspicion that we are not pro-business, even when we are.”

Kunin and Sylvester got off to a rough start, though. He urged her to back conservative Democrat Treasurer Stella Hackel in the 1976 primary for governor, but Kunin backed Hackel’s opponent, Brian Burns, because she preferred his positions on women’s issues.

“[Sylvester] was quite upset … and remained so for quite a while,” recalls Kunin.

In the end, however, as Kunin rose through the ranks in state politics, Sylvester’s hard feelings softened. By the time she was governor, he had returned to his rightful seat beside the throne, serving as the chairman of her council of economic advisors. He handpicks its members with the gov’s blessing, according to Terry, in an effort to bring together male and female leaders in business, politics, nonprofits and higher education.

Sylvester makes himself available to any aspiring politician — be they Democrat or Republican, blessed with name recognition or not.

“He has a great intellect, a great knowledge of Vermont and great contacts,” says Mark Snelling. “He was a mentor of mine. I started working on my dad’s 1976 campaign and got to know him. Shortly thereafter, I really wanted to do something and get more involved, and he turned to me and said, ‘Give these people a call,’ etc.”

Discretion is always part of the deal. For all his influence, Sylvester’s name rarely appears in the Vermont media — even when he’s the subject of a story. Retired businessman and author Bill Schubart broadcast a Vermont Public Radio commentary in August lamenting Vermont’s “shadow cabinet,” whose members “vet and bless candidates of their choosing and will.” There was no direct mention of Sylvester, Coates or Hackett, but that’s precisely the trio he was referring to.

Besides declining to be interviewed for this article, Sylvester at one point tried to put the kibosh on it.

The official reason: His employer does not allow brokers to speak to the press.

The unofficial reason: The gag order makes him invaluable as a confidant to politicians. Reporters, too. Sylvester served as a loyal anonymous source for the late Peter Freyne and visited the ailing political columnist every day during the last months of his life. At Freyne’s memorial service, he declined to be one of the speakers.

That self-effacement extends to Sylvester’s community-service work. He and his wife, Joan, have given generously to organizations that work with the mentally ill, the homeless, and the poor.

Snelling recalls when Sylvester was stepping down from the board of the Medical Center Hospital of Vermont — now Fletcher Allen Health Care — after nearly a decade of service. MCHV held a customary dinner in honor of the departing board members.

“He had done a tremendous amount of work for that hospital and had mentored many of the trustees. But, when the night of the dinner arrived, Harlan was nowhere to be seen,” says Snelling. “That’s typical of Harlan — work behind the scenes and disappear when the limelight arrives.”

Only once — during Gov. Howard Dean’s run for president — was Sylvester properly outed.

The American Prospect credited Sylvester for the Democrat candidate’s fiscal conservatism, noting, “Dean has been guided for more than a decade by a behind-the-scenes kingmaker named Harlan Sylvester, a senior executive at Salomon Smith Barney in Burlington who chairs Dean’s council of economic advisers.”

No mention that Sylvester’s Vermont license plate number is “100” — the first number the governor can assign to “regular” citizens after the 99 assigned to high-ranking elected officials, judges and cabinet secretaries. That was a little gift from Gov. Dean.

But search Google for images of Sylvester, and three gravestones pop up — with other guys’ names on them. Sylvester even managed to stay out of his UVM college yearbook.

“He always keeps you guessing — he never plays out his hand,” says Terry. “That’s what makes him so mysterious.”

Always a Horse in the Race

When it comes to party loyalty, Sylvester is flexible. Despite being a lifelong Democrat, he easily went from championing Dean, a Democrat, to backing Douglas, a Republican. Ditto Dubie — all three talk plenty about lowering taxes and keeping the wealthy from leaving Vermont.

Former state Sen. Jim Leddy says he remarked to his longtime friend after Douglas was elected: “Harlan, you went from supporting Howard Dean to supporting Jim Douglas, and you never dismounted.”

In fact, Sylvester’s support assured that Dean faced minimal challenges — particularly from Republicans. It also kept another powerful pol at bay: Bernie Sanders.

“One of the reasons the Republicans never ran anyone serious against Howard Dean is because of Harlan’s support and his own personal background — son of a stockbroker, from a Wall Street family and a Protestant; he was one of them,” says Nelson. “So they had no trouble voting for him. It also worked to keep Bernie from ever coming back to run for governor.”

U.S. Sen. Bernie Sanders is the most powerful Vermont politician who has never sought Sylvester’s counsel — nor has Sylvester reached out to the Brooklyn-born self-styled socialist.

“To the best of my knowledge, I have never talked to Harlan Sylvester in my life, and if he walked up to me, I would not know who he is,” Sanders says.

Sylvester and Doug Racine have a similar relationship.

When he served as lieutenant governor during Gov. Dean’s tenure, Racine says, he met with Sylvester several times but never asked for his advice.

“Howard thought Harlan was someone I should meet with, so I did,” says Racine. “His big thing is trying to lower taxes for wealthy Vermonters, and I didn’t agree with him on that. I believe in a progressive income tax, and I don’t believe he does. He works for wealthier people, and that’s OK, but I know a lot of people who are wealthy and who do support a progressive income tax.”

Racine’s more liberal tax views certainly cost him Harlan’s support when he ran against Douglas in 2002. Sylvester was a major Douglas booster.

“Harlan had a lot of influence at that time, and I even heard from some of my friends who said Harlan had asked them not to support me when I ran for governor,” says Racine. “And they didn’t — at least not publicly.”

Racine lost to Douglas by just a few thousand votes.

Former House Speaker Ralph Wright also rubbed Sylvester the wrong way because of his liberal interest in levying higher taxes on wealthier Vermonters.

“My only memory of any relationship was that he once sent a check through someone to me for one of my annual fundraisers,” says Wright from his Florida home. “In the envelope containing the check was a note saying something close to ‘Hope you can do more for me this session than you have in the past.’ I ripped up the check and had it sent back — I may have said something nasty in reply.”

Wright says he also recalls Dean once saying that, during a meeting with his council of economic advisors, Sylvester said, “Ralph Wright is a dangerous man.”

“If he didn’t say it, I’m reasonably sure he would have agreed 100 percent. And, may I say with some pride, I hope he was right,” says Wright. “To be fair, Harlan had reason not to think too highly of me, as I always threatened to place a sales tax on stock-market transactions. Never did, but it still resonates as not that bad an idea.”

Once and Future Pols?

Sylvester has been known to say that, spouses aside, he’s the first person the governor talks to in the morning and the last person the governor speaks to before going to bed at night.

That kind of influence causes Bill Schubart to wonder: “Is power given, or is power earned, and what’s the balance? Does Harlan’s political influence derive from his ability to raise money, trust or his political instincts? Or is it a fealty?”

More importantly, can it last?

“I hear an awful lot about him. His name comes up regularly in conversations, and there are definitely still a lot of people who talk to him,” says House Speaker Shap Smith, 44, who says he has never spoken to or met Sylvester.

Sylvester’s connections with two younger pols demonstrate some of the ways in which he continues to be “useful.” Auditor Tom Salmon, a 47-year-old Democrat-turned-Republican, and Chittenden County State’s Attorney T.J. Donovan, a 36-year-old Democrat, have both held political fundraisers at Sylvester’s favorite watering hole: Burlington’s St. John’s Club, a private club with blue-collar origins — just like Sylvester. He goes there at least once a week.

Sylvester is believed to have been the strategist who pushed Salmon to leave the Democratic Party with the goal of challenging Sanders in 2012 — Salmon had spoken out against legislative Democrats’ spending plans, giving Gov. Douglas additional political cover. Plus, Salmon’s political pedigree harks back to Sylvester’s heyday in his father’s administration.

Sylvester stood by Salmon through his subsequent drunk-driving arrest and public displays of erratic behavior. The auditor declined to be interviewed about his relationship with Sylvester.

Donovan was a clerk at the now-defunct Longe Brothers store in Burlington’s South End when he first met Sylvester.

On Sundays, Sylvester would meet up with former Merchants Bank president Dudley Davis and others, and go for long walks through Burlington and Winooski. Afterward, they’d shoot the breeze inside the store, roping Donovan into the conversation.

“Those guys treated me like a friend, not like some kid,” says Donovan. “It was a very formative experience for me to work in that store. It was the best political education I ever received.”

They also supported Donovan when he needed it later: Davis helped him get a scholarship to go to college. Sylvester provided political guidance and helped the attorney raise money during his first, and spirited, race for state’s attorney in 2006. Donovan briefly considered a run for lieutenant governor this year, but opted for a reelection bid.

Perhaps Sylvester sees a brighter path down the road for his political progeny?

The pair talk regularly, but more often about family and basketball than politics, according to Donovan. Sylvester has a reserved courtside seat at Rice High School, where he watches his grandson play. He lives a short walk from the school. Sylvester also works out every day for an hour on the StairMaster.

Donovan still sees him as “the guy you would seek, at least from my perspective, to get advice and counsel on political questions; he’s a guy whose judgment I trust.”

Sylvester provides something else to up-and-coming pols that most highly paid political consultants can’t: an encyclopedic knowledge of Vermont political history.

“Because he’s been doing it for so long, he’s seen innumerable political and fiscal cycles. When you talk to him, it’s not about what’s going on right now, but what’s gone on three times before,” says 36-year-old Neale Lunderville, Douglas’ longtime political aide and current secretary of administration. “That kind of perspective is invaluable, and it’s often missing in today’s politics.”