(Editor’s Note – The Observer began this documentary project in January 2011 with a coffee and a bull session with Neil O’Leary. We asked if he were willing to let us occasionally peek behind the curtain of his mayoral campaign, to sit in on strategy meetings, and to ride along with him on election day. The only ground rule was that sensitive information could not be published until after the election. Observer publisher John Murray first met O’Leary on election day 1995 when O’Leary was the driver for seven-term mayor, Mike Bergin, and Murray was shadowing Bergin for the day. Bergin lost that election to Phil Giordano, and at a post-election party, at the Hills Restaurant, O’Leary told Murray that the Democrat Party was now in the hands of Mike Jarjura. Six years later Jarjura was elected mayor and served for ten years, until November 8th  2011, when Bergin’s young driver picked him off. The project was published in November 2011 in print, but was posted online six years later, November 9th, 2017. This is the story of the 2011 mayoral race in Waterbury.)

                                 Story and Photographs By John Murray

   At the outset Neil O’Leary’s campaign for mayor had the aura of General George Patton storming across Europe at the end of WWII – nobody could stop him.

   O’Leary announced his candidacy on February 6th inside a dilapidated store front on East Main Street in downtown Waterbury. During his speech he laid out his platform and rationale for seeking the office of mayor. At the end of his speech O’Leary sang along to Petula Clark’s song “Downtown”, and seemed to be having the time of his life.

In early February O’Leary announced he was seeking the Democrat nomination for mayor. At the end of his speech he sang along to the tune of “Downtown” by Petula Clark. Downtown revitalization was one of the key issues of his campaign.

   A month later, on March 1st, O’Leary held his first fund raiser at the Ponte Club and a 1000 people showed up. Traffic was snarled for half a mile leading into the event and hundreds of people were turned away. You could feel an earthquake rumbling across the political landscape in Waterbury. O’Leary had burst out of the starting gate with such force that it was nearly impossible to sustain.

O’Leary greeting old friends at the Ponte Club fundraiser.

   O’Leary was sure that Mike Jarjura, the five-term incumbent, was not going to be his opponent. Two years earlier O’Leary had planned to run for mayor because Jarjura had said he would not seek re-election in 2009. O’Leary was ready to run but Jarjura changed his mind and decided to seek re-election. Undaunted, O’Leary believed he could defeat Jarjura in a primary, and was intent to follow through with his 2009 campaign. Party leaders feared a titanic collision between the two popular men, and a meeting was arranged to broker a deal. If O’Leary stepped aside in 2009. Mike Jarjura promised to support O’Leary in 2011, as did the other 11 men in the room.

O’Leary was a powerful police chief in Waterbury for many years and is credited with creating one of the most dynamic PAL programs in America. Under his leadership he took the program from 100 kids to 3000 kids, and drew national attention to the program.

After standing down in a primary challenge in 2009, O’Leary kept a close eye on Mike Jarjura and the promise that Jarjura would support his candidacy in 2011.

   At the end of 2010 there were signals that Jarjura wasn’t going to live up to his promise. He had spent the better portion of the year campaigning for state wide office, first running for governor, then Lt. governor, then comptroller, all while coveting the position of attorney general. In the end Jarjura zeroed in on the comptroller position and tried to win the party nomination at the Democrat convention. He didn’t get the nod, and sources have confirmed with the Observer that Jarjura had promised gubernatorial candidate Dannell Malloy that he would accept the delegate’s choice and not force an expensive primary.

   Weeks after making the pledge to Malloy, Jarjura filed papers to challenge Kevin Lembo in a primary for comptroller, and was subsequently crushed. Besides the defeat, Jarjura had infuriated Malloy by forcing a primary, an infraction Malloy would not easily forgive, or forget.

O’Leary and Governor Dan Malloy attended the Albanian Festival on Raymond Street in the South End of Waterbury in June.

   After Malloy was elected governor in November 2010, O’Leary said he was approached by Jarjura who asked him to intervene and help Jarjura get a job in the Malloy administration. O’Leary had been a staunch Malloy supporter, and O’Leary’s campaign manager, Gary O’Connor, had attended law school with Malloy at Boston College. Jarjura wanted them to use their juice with Malloy to get him a job, or he would reconsider and run for mayor again in 2011. It was a game of chicken, and O’Leary said he wouldn’t embarrass himself by asking the Governor to find a job for Jarjura, because Malloy disliked and distrusted the mayor.

   “I told Mike Jarjura that maybe Gary O’Connor or Ned Cullinan (Democratic Town Chairman) might help him,” O’Leary said, “but I don’t think even God could help him with Malloy, because he lied to the governor and was disloyal.”

  With his quick pre-emptive strike in February and March, O’Leary was convinced that Jarjura would not follow through with his threats to seek re-election. The entire establishment of the Democrat Party was supporting O’Leary, including the incumbent Democrat aldermen and board of education members. The only person who wasn’t following through on the promise of 2009, was Mike Jarjura, who told the Observer in March that, “we live in America. I have a right to change my mind if I want to. I’m a young man and I shouldn’t be chased out of office by my own party.”

Politics soured the relationship between O’Leary and Jarjura, but for nine years they were friendly as they tried to work together to improve the city.

   But Jarjura was cornered. He had no chance of winning the Democrat nomination for mayor, and challenging O’Leary in a primary was sketchy at best. Jarjura’s strength lay out in the general election when his conservative views and financial expertise made him an attractive candidate to disenfranchised Republicans. He openly talked about heading straight to November by running as a petitioning candidate, but when Jarjura announced he had switched parties on May 31st to become a Republican, a second earthquake shook the 2011 mayoral race.

   “I didn’t see that one coming,” O’Leary said. “It was a brilliant move by the Republicans, but I didn’t see Mike Jarjura destroying twenty years of Democrat loyalty. He threw it all away because he was so desperate to stay in power. Make no mistake about it, Mike Jarjura switched parties because it gave him an opportunity to remain mayor. It had nothing to do with political ideology.”

   And now O’Leary was in a dog fight with a five-term incumbent mayor, and dog fights can get ugly.

A campaign meeting in June centered on an impending interview with WATR radio, and what tone should O’Leary set. Should he criticise Mike Jarjura, or focus on his own campaign platform. There was some dissent at the meeting, but ultimately O’Leary wanted to use the radio interview to forward his own agenda. At the meeting, from left to right is Saranda Belica, Atty. Gary O’Connor, Atty. Dick Scappini (back turned), O’Leary, Atty. Paul Pernerewski and Atty. Don McPartland.

Seconds after securing the unanimous support of the Democrat Town Committee at the Democrat Convention in July, O’Leary stopped to greet his family, and bring a few on stage with him. His ten-year-old daughter, Maggie, is on the far left. O’Leary’s first wife, Kathy, is third in from O’Leary, and his second wife, Dale, is next to him. Both of those marriages ended in divorce, but in June 2009 O’Leary re-married Kathy, which bizarrely became a huge campaign issue since they remarried the day before he retired from the Waterbury Police Department, and if he should die before her, she would get his pension benefits.

O’Leary and his two children, Patrick and Maggie.

   Another Democrat, J. Paul Vance Jr., was still lurking as a possible challenger to O’Leary within the party, but when Vance was hired by the state he withdrew his name from consideration. By Labor Day the race had taken shape as Larry De Pillo emerged as the Independent Party candidate, launching his fifth attempt to be elected mayor of Waterbury, Jarjura was the Republican candidiate, and O’Leary was the standard bearer for the Democrats.

   What occurred in September and October left experienced political operatives stunned. Instead of a raucous political campaign, Waterbury ended up in the midst of a nasty divorce between Jarjura and O’Leary, with De Pillo staying quiet on the sideline. In time the specific issues will fade from the city’s collective memory, but the foul taste will remain. In the span of two months there were allegations that the mayor had profited from human trafficking by renting a property he owned to a Korean brothel. There were revelations that O’Leary had secretly remarried his first wife the day before he retired as police chief in Waterbury in 2009, and that he hadn’t shared the news with sister, who was his wife’s boss.

Kathy O’Leary (current wife), Christine Murphy (sister,) and Dale O’Leary (ex-wife) at the Democrat convention in July.

   The mayor and one of his aides repeatedly alluded to an impending FBI arrest of O’Leary, and used the rumor mill to slander the city’s former top cop with tales of gambling, drinking and two car crashes. Mud flew fast and furious and every few days seemed to bring a new revelation that trashed one man or the other.

   “This has been eye-opening for me,” O’Leary said. “I’m surprised how ruthless Mike Jarjura and his campaign manager Bobby Brown have been. These guys used to be my friends.”

   But in some ways, just like General George Patton 67 years ago, Neil O’Leary provided the stiffest challenge to  his own aspirations. O’Leary had spent his career as a police officer, where orders are followed in a military style chain of command. Politics are different. When you ask a political participant to perform a task you seldom here “yes sir”, and more likely than not you’ll hear, “why?”

   O’Leary admits he has had to adjust his expectations, and during a conversation with the Observer in July, he confessed he wasn’t sure he still wanted to be mayor. It was a few weeks before the Democrat convention and he was being ravaged by political posturing and Democrat in-fighting. Factions inside the party were demanding representation on the ticket, and powerhouse Karen Mulcahy was threatening to run as a petitioning candidate for mayor in November if son Ryan didn’t land a coveted alderman position. There were rumors that State Representative David Aldarando was trying to intimidate business owners in the South End to not support O’Leary until he provided a budget to mobilize the Hispanic vote. And there were rumors that J. Paul Vance Jr. was angling for O’Leary and O’Connor to help get him get a job in the Malloy Administration.

   “I don’t know,” O’Leary said. “This is nuts, and I must be nuts to want to be mayor. I might be better off collecting my pension and going fishing every day. As the police chief everyone was really happy with the job we were doing, especially at PAL. There was very little criticism. Now, no matter what, there are at least 40% of the people that don’t like me or what I’m doing. It’s a different feeling and I’m getting used to it, but I’m still new at politics.”

   His doubt evaporated quickly and within two weeks peace had been restored to the Democrats and they began to focus on the opposition, and stopped tearing at one another.

   The night before the election O’Leary developed a stye in his right eye. O’Leary pressed a compress onto the throbbing infection and watched ESPN’s Sport’s Center for the second time that evening. He nodded off for a bit and awoke at 5 am. His brother Kevin picked him up at 5:20 and he was campaigning at six am.

   It was a crazy day of bopping around Waterbury like a heated neuron. He campaigned at Kennedy High School, at Lady of Loretto Church in Bunker Hill, Chase School, Crosby High School, Tinker School, visited at Blessed Sacrament School, visited headquarters in downtown and on South Main Street, and in between all the campaigning O’Leary paused to visit his Aunt Edna at Apple Rehabilitation, and to stop and visit the grave sites of his parents, Cornelius and Margaret O’Leary, at a private cemetery in Waterbury’s South End.

  Greeting students at Walsh Elementary School in 2008.

The Pontelandolfo Community Club staged the Festa Di San Donato in early August. The festival began with a Mass at St. Lucy’s Church, followed by a two-mile procession to the Ponte Club. As the procession turned onto club grounds it passed giant O’Leary For Mayor signs, which drew a big laugh from Bishop Peter Rosazza. On the far right of the photograph is U.S. Senator Richard Blumenthal, and to the far left is Tony Rubbo, president of the Ponte Club.

Personal tension mounted between O’Leary and Jarjura as the campaign unfolded. Weeks after Jarjura switched parties to become a Republican, the two candidates collided at a Brownfields Remediation press conference at PAL on Division Street. When Jarjura marveled at the long hours Congressman Murphy was working in D.C., he said he personally could not keep up that pace without falling asleep at his desk. Murphy chuckled, and O’Leary nodded his head because the mayor’s work ethic was a key issue of the O’Leary campaign.

Sparring on WATR with Mayor Mike Jarjura as host Larry Rifkin looked on.

All four of O’Leary’s grandparents were born in Ireland, and he embodies many characteristics of the Irish – a love of talk and laughter. One of O’Leary’s favorite campaign events was marching in the St. Patrick’s Day Parade through the South End of Waterbury. To the right of O’Leary is Ernie Brunelli, a Democrat member of the Board of Aldermen.

Former mayoral candidate Karen Mulcahy threatened to run in the general election if O’Leary didn’t place her son, Ryan, on the ticket as a Board of Aldermen candidate. She told O’Leary, “I won’t win, but neither will you.” Ryan Mulcahy, right, then became a aldermen candidate.

There were more than six mayoral debates scattered throughout the city, and all three candidates conducted lengthy interviews on WATR and with The Waterbury Observer.

During the final two months of the campaign O’Leary hosted his own 30 minute show each Wednesday night on Public Access TV. It was a direct way to deliver his message to the voters.

   The night before the election O’Leary said he didn’t sleep well. “I was wondering about our strategies,” he said. “What worked, and what didn’t work. I thought about all the money we spent, and then my eye got infected.”


Election Day

The day began for O’Leary when he reached headquarters at 5:30 am and headed up to Kennedy High School. It was a remarkably warm day in November and the temperatures reached into the high 60s, but at 6:30 am, with the sun peering over the horizon, it was cold. O’Leary is pictured above greeting Board of Aldermen president, Paul Pernerewski.

O’Leary was working his phone, and coffee, all day long.

Chatting with the father of Waterbury Police Chief Michael Gugliotti.

A mid-day visit to his daughter Maggie’s classroom at Blessed Sacrament School.

O’Leary is energized around kids and used election day as a civics lesson at Blessed Sacrament.

For a few hours Maggie got to escape from school to help her father cast his vote at Kennedy High School and to poll stand in front of the school engaging voters and entertaining candidates.

O’Leary, an Irish Catholic, has always looked up to John Kennedy as an inspiration. This JFK bust is at the entrance to Kennedy High School on Highland Avenue in Waterbury.

Back in campaign headquarters O’Leary caught up with campaign co-chairman Fran Sullivan and juggled phone calls and time constraints.

Picking Maggie up at the end of the school day was a grounding experience in a whirlwind day.

Greeting Independent Party mayoral candidate Larry De Pillo in front of Tinker School in the Town Plot neighborhood. The two men remained remarkably cordial to each other during the campaign as De Pillo was intent to let O’Leary and Jarjura slug it out, and hoped to quietly slide right up the middle to victory.

In the Bunker Hill neighborhood O’Leary spent some time giving an interview to the Republican-American newspaper’s political reporter, Penny Overton.

One of the strangest moments on election day occurred when O’Leary received a telephone call from a representative of a company that specialized in background searches. The caller thanked O’Leary for his business, to which O’Leary said he hadn’t done business with them. They went through the contact information and it turned out that transactions had been conducted under O’Leary’s name, and his private cell phone number was listed as the contact. O’Leary questioned the transaction and the rep said the transactions were initiated from an e-mail address listed as fdavino@carpinmanufacturing.com. Astounded, O’Leary put the call on speaker and had the representative go through the information again. “That’s weird,” O’Leary said. “They use my name and contact information, and Frank’s e-mail address. It’s awfully odd.” Frank Davino’s brother, Joey, had become a central figure in the campaign when Mayor Jarjura had personally intervened to assist him in gaining unemployment compensation, even though he had been arrested for bilking the city out of honest services.

For the past several campaigns Democrat candidates have left the polling places in the early afternoon to rendezvous at the Portuguese Club on Baldwin Street for some warm, hearty food before heading back out into the cold. The tradition was started by Paul Nogueira, left, who was a Democrat aldermen. Nogueira is now a Republican, but he said the meal isn’t about partisan politics, it’s about breaking down barriers and enjoying friendship. This was O’Leary’s first election day invite.

A crucial moment in the campaign occurred when O’Leary refused to pay friends of State Representative David Aldarando to organize a get-out-the vote campaign in the largely Hispanic 75th District. O’Leary called the request for $50,000 a “shakedown”, and days later the only Hispanic on O’Leary’s ticket, and a friend of Aldarando’s, quit the Democrat slate. However, a motivated group called Latinos Unidos stepped forward to support O’Leary and help run his South End headquarters. O’Leary is pictured here with Geraldo Reyes Jr. (sunglasses) in the South End HQ.

Back at campaign headquarters the get out the vote effort was in full swing. As voters cast a vote at their polling place, the information was relayed back to headquarters and their name was crossed off the list. As the day unfolded efforts intensified to reach out to those previously identified as supportive to O’Leary, and they were contacted and encouraged to vote. If transportation was an issue, cars were sent to ferry the voter to the polls.

There is a long and storied history of ethnic politics in Waterbury, mostly between the Irish and the Italians. New groups are beginning to emerge in Waterbury and O’Laery had a small group of Albanian volunteers encouraging members of the Albanian community to cast their vote for O’Leary.

Saranda Belica was a full-time volunteer inside the O’Leary campaign and in the late afternoon displayed a lucky jewelry piece given to her by her grandmother back in Struga, Macedonia. She said the piece would help O’Leary win later that evening.

Despite a highly contentious and deeply personal campaign,  O’Leary and Mayor Michael Jarjura were gracious and friendly when they came face to face at Chase School in the East End of Waterbury.

Not so gracious was the performance of Robert Mulcahy, center, who razzed Jarjura at Chase School until a police officer was dispatched to quiet him down.

Zig-zagging across the city O’Leary campaigned with City Clerk Michael Dalton at Crosby High School.

O’Leary has developed an astounding ability to connect with people from all walks of life. With a powerful handshake, and a slap on the back, O’Leary pulls people into his space to share a joke, or ask how the family is. On election day he bear-hugged, kissed and joked his way across the city.

O’Leary campaign spokesperson Raechel Guest waited with O’Leary outside Kennedy High School for a TV crew to show up for a live broadcast.

Democrat Town Chairman Ned Cullinan, left, consulted with Atty Dick Scappini  about voting numbers and patterns as the day headed towards the home stretch.

O’Leary greeted voters at Kennedy High School in the Town Plot neighborhood of Waterbury during the final hours before the polls closed.

The Returns

After the polls closed Sue Napoli greeted her husband, Ron, like a long-lost friend. Ron Napoli, a former aldermen and mayoral candidate, is a work horse in the Democrat political machine, and had spent the final days of the campaign immersed in efforts to get out the vote.

O’Leary and his wife, Kathy, relaxed in a private area above campaign headquarters while waiting for the first returns. Republican-American reporter Michael Puffer is on the left.

Secluded in a securities office two floors above O’Leary campaign headquarters. the candidate, right, and his inner circle, anxiously awaited the first returns of the evening. Waterbury Police Chief Mike Gugliotti is in the foreground compiling results, while O’Leary’s wife, Kathy, and co-campaign manager, Gary O’Conner, looked on.

Internal polls had forecast a solid victory for O’Leary, but after years of positioning himself for a mayoral run, a 10 months of hard campaigning, O’Leary was apprehensive and nervous as the phone rang and returns began to pour in.

And within minutes the victory was his and he fired off a fist bump with Police Chief Michael Gugliotti.

A congratulatory embrace with his wife, Kathy O’Leary.

A powerful and heart-felt embrace from one of his best friends, Police Chief Michael Gugliotti, who had served as O’Leary’s personal aide when O’Leary ws the police chief before him.

Well wishers surrounded O’Leary as he made his way to the stage back inside campaign headquarters. Here O’Leary is being greeted by Jim Gatling from NOW Inc..

Leaders of special interest groups were out in force inside O’Leary headquarters. Kevin Egan is the president of the Waterbury Teachers Union and had helped deliver votes to O’Leary.

O’Leary took the returns upstairs from his headquarters and could hear the crowd erupt when it was clear he had won the election. Moments later O’Leary made his way down to the first floor where he was embraced by a sea of adulation. Thirty minutes before there was barely a hundred people in the room, but by the time O’Leary entered as mayor-elect, the crowd had swelled to five or six hundred. When he took the stage to thunderous applause and a flood of bright TV lights, he looked momentarily stunned. His hands were thrust into the air by his co-campaign mangers Fran Sullivan and Gary O’Connor, and then Governor Dannell Malloy joined him on stage with Lt. Governor Nancy Wyman. Afterwards a joyous group of O’Leary supporters flooded Drescher’s Restaurant for an O’Leary victory party.

Connecticut Governor Dan Malloy showed up to personally congratulate Neil O’Leary and vowed to work with the city’s new mayor to improve the quality of life in Waterbury.

O’Leary beamed as Governor Malloy touted his victory, and Lt. Governor Nancy Wyman beamed as well.

The personal animosity between O’Leary and Jarjura made the final weeks of the campaign difficult for the city as the rhetoric cranked up to near slander. O’Leary’s ads depicted Jarjura with a satchel of gold slung over his shoulder on his way to Middlebury, effectively looting the city. Jarjura’s ads published photographs of a serious car accident O’Leary survived two years ago and stated O’Leary would be “a wreck” of a mayor. Jarjura also went after O’Leary’s “secret marriage” and said the former police chief could not be trusted. Railing on his professional record was fair game, but when Jarjura started going after O’Leary’s personal life and family, O’Leary was furious. “He stepped over the line and I’m not going to forget that,” O’Leary said. “We hit him on issues, but he dragged my family into this.” O’Leary’s anger was quickly tempered on election night when he clobbered Jarjura at the polls, and then the mayor showed up at O’Leary headquarters to personally congratulate O’Leary and promised to work closely with him in the next month to provide a smooth transition. O’Leary is pictured above watching intently as Jarjura addressed the excited crowd gathered in O’Leary headquarters.

 O’Leary’s mentor and best friend is 7-term Waterbury mayor, Mike Bergin. O’Leary learned old school politics as a Bergin family friend, and as Bergin’s driver in the 1990s. O’Leary’s victory was a powerful moment for both men.

A jubilant O’Leary addressed his supporters and the media. The hard work had paid off.

Members of the Jewish Orthodox community were on hand to support the O’Leary victory.

A congratulatory kiss from former Republican alderman Joey Pisani, the owner of Pisani Steel.

   While campaigning outside Kennedy High School O’Leary remembered his experience escorting JFK Jr. around Waterbury on the 25th Anniversary of the school being built. Kennedy had come up from NYC in a yellow convertible VW bug, and the two had visited the balcony at the Elton Hotel where JFK had spoken from on the eve of his election in 1960. There was a lot of remembering and laughing during the 14 hours of campaigning on election day, but perhaps the most significant thing that happened for O’Leary besides winning the election, is what transpired between two men standing in the parking lot of the Republican-American newspaper two hours after the polls closed. O’Leary was headed into the Republican-American newsroom for the traditional interview on WATR radio, and he encountered Mike Jarjura walking out of the building. It was just the two of them, alone, and O’Leary said they shook hands and Jarjura promised the mayor-elect he would fully cooperate to ensure a smooth transition of power.

   O’Leary said he thanked Jarjura, and then told him that he was deeply disappointed in the personal attacks on the O’Leary family.

   “He told me the attacks had gone too far,” O’Leary said. “They had been too personal on both sides, and he apologized. It will take us both some time to get over this campaign, but we were friends before, and I hope we can be friends again.”

   After his interview on WATR, the mayor elect headed down to Drescher’s Restaurant to celebrate with a few hundred of his best friends, and went home to bed around 1:30 am.

   “I hadn’t slept more than a few hours when I sat up in bed and started thinking about all the awesome things that I want to do in the city,” O’Leary said, “ and then I couldn’t get back to sleep because I started thinking about all the responsibility I have to move Waterbury forward.”

Ten-year-old Maggie O’Leary was hoisted into the air and kissed by her father after he captured the mayor’s seat in Waterbury. The image above was made as O’Leary made his way through a raucous crowd of supporters towards the victory stage. Half way through the crowd O’Leary spotted his daughter, picked her up in front of hundreds of supporters and journalists, and gave her a kiss that neither one will ever forget.