Neil O’Leary On Cusp Of History

Waterbury Mayor Neil O’Leary

Column By John Murray

   This will be the 13th mayoral race I’ve covered as a journalist in Waterbury, and the most uneventful.

   While there is the possibility that one of the four challengers might pull a David versus Goliath shocker on election day, the stone-cold truth is that Neil O’Leary (Goliath) will stomp his opponents – Ray Work, Vernon Matthews, Keisha Gilliams and Ty McElrath – and march into a fourth and potentially historic term inside City Hall. If he wins on November 5th, and finishes his four-year term, Neil O’Leary will become the longest continually serving mayor in Waterbury history.

   Neil O’Leary will never tell you this, of course, or say that he expects to clobber his challengers on November 5th – that would be poor form. Instead, O’Leary has been working hard these past few months attending events, dominating two mayoral debates, and showing up at community functions that in non-campaign mode he would have sent a staff member to.

   Mayor O’Leary is engaged in this election cycle and is undoubtedly looking forward to completing what many have surmised is his final political campaign in Waterbury. His biggest opponent? Voter apathy. The first mayoral race I covered in 1993 was between incumbent Democrat Mike Bergin, Republican Steve Somma and independent candidate Andy Michaud. There were 30,490 votes cast, and that number has steadily declined since.

   When O’Leary knocked off five-term incumbent Michael Jarjura in 2011 there were 16,636 votes cast. In 2013 there were 12,540 votes cast, and in 2015 there were 11,510 votes cast.

O’Leary, right, and Jarjura in 2011.

   From 1993 to 2015 – while the city’s population remained basically the same –  nearly 20,000 less voters cast a vote for mayor in Waterbury. The decline has been attributed to a shifting demographic, Waterbury’s history of corrupt politicians, and a younger generation not engaged in the civic life of the city.

   “I’m worried about this downward trend,” O’Leary said. “We need more people involved.”

   While not a mind reader or a fortune teller, it is fairly easy to predict O’Leary will cruise to re-election. Why? Let’s break it down.

   • While money isn’t everything, it often is a strong indicator of community and business support. In the 2019 campaign O’Leary has collected $195,000 and his four opponents have a combined $10,000. That gives O’Leary a 20-1 financial advantage.

   •  Shockingly, the Independent Party that rocked the political establishment in 2001 by flushing Republican candidates to the sidelines, has raised less than $200.

   • During the first debate hosted by the Waterbury Chamber of Commerce on October 2nd, O’Leary clearly had the experience and knowledge to answer detailed policy questions and he commanded the stage. His three opponents at that debate – Work, Matthews and Gilliams – were at various times flustered or ill prepared to answer questions asked by moderator Anne Karolyi, the managing editor the Republican-American newspaper. Write-in candidate Ty McElrath was not invited to the Chamber debate, which was unfortunate, because he brought youth, idealism and pizazz to the second debate hosted by the Greater Waterbury Chapter of The National Congress Of Black Women.

   • When O’Leary upended five-term mayor Michael Jarjura in 2011 he accomplished a mini-miracle by uniting two bitter factions of the Democratic Party, and has avoided internal squabbles and primaries that plagued the party for decades. As an example, former mayor Mike Bergin ran for mayor 9 times, and faced a primary opponent nine times.

   • Democrats outnumber Republicans in Waterbury 26,000 to 7500, a statistic that suggests a Republican can’t win in the city without a splintered Democratic Party (which happened in 1985 and 1995 when Joe Santopietro and Phil Giordano were elected with strong support from an alienated wing of the Democratic Party. A splinter wing doesn’t exist right now, but expect it to re-emerge when O’Leary leaves the stage)

   • Money and control of the political chessboard is important, but what O’Leary has accomplished in his eight years as mayor is impressive. Whether you like him or not, he has been a force of nature in launching new projects, securing state and federal funding, growing the grand list, creating jobs, and collaborating with elected officials up and down the political food chain.

   Predicting an O’Leary landslide doesn’t infer that his opponents aren’t nice people, because they all certainly seem to be. But to varying degrees they come up empty as serious opponents to a well-funded and politically experienced mayor who has run the city for the past eight years. Let’s take a peek at the candidates.

   Vernon Matthews was the first candidate to challenge O’Leary when he announced in the dead of Winter that he was seeking the Republican nomination. Matthews is an incumbent Republican alderman and he rides city buses every Wednesday to talk to people about their concerns are. This is an excellent idea because what Matthews hears on the bus is a far cry from what O’Leary hears at meetings inside City Hall, or at Chamber events.

Vernon Matthews

   Matthews took his campaign straight to the people. His bid for the Republican nomination was  thwarted a week before the nominating convention, however, by the emergence of Ray Work who announced he would also seek the GOP nomination. Matthews is African-American and told Republican-American reporter Michael Puffer that Work’s candidacy was an attempt to block him from becoming the first black to head a major party ticket in city history.  Matthews told Puffer the move was racist.

   Puffer published Matthews statement – that’s what reporters do – but Matthews immediately said he was misquoted and denied ever saying it. (Puffer now tapes every conversation with Matthews).

    At the nominating convention Work was chosen to lead the Republican Party and Matthews was nominated for alderman, and snubbed as a mayoral candidate. The GOP turned its back on Matthews mayoral campaign and shattered his dream of leading the ticket and making history. The GOP showed so little respect (the charges of racism was alienating) that no one nominated him. The snub led Rodney Parker to confront the GOP Convention where he refused to listen to party chairman Bill DeMaida’s calls to sit down and called the process “unfair” and “bull”.

   Matthews was visibly upset at the convention and within a few weeks accepted an offer to run for mayor atop the Independent Party ticket, while retaining his alderman slot on the Republican ticket. Work issued a statement calling on Matthews to step down from the GOP ticket stating it would be impossible to oppose Work for mayor, yet run on his under ticket.

   Matthews ignored Work and will appear as both the Independent Party’s candidate for mayor and the Republican candidate for alderman from the 2nd District. That’s ambitious on Matthews part, but he has not delivered details of his plan to cut taxes and recruit more business to the city to reduce the mill rate.

   And details have been lacking from all of O’Leary’s opponents.

Ray Work

   Ray Work is as nice a man as you’ll meet in Waterbury. He is the chairman of the City Plan Commission, a small business owner, has been involved with the Boy Scouts of America for years, and has been a loyal volunteer to the local GOP and an occasional sacrificial lamb. Twice his name was placed before the electorate in the 75th District state representative race and he was trounced by 4-1 margins.

   At times it is difficult for the Republican Party to find candidates to run in seemingly unwinnable districts, but Ray Work has proven to be a loyal soldier, and he appears to be falling on the sword again for the GOP this cycle.

   A looming question is why?

   In his last race for state representative published reports stated that he had more than $300,000 in liens on his house. It’s a pretty hard sales pitch to preach financial responsibility when you are personally under water to the federal government for unpaid taxes. And sure enough the story came back to bite Work with a front-page story in the Republican-American about the liens.

   Work said he views his IRS debts as a loan from the federal government.

      “If anything, it shows I know how to manage things when they are not as good as they can be,” Work told the Rep-Am, and he said voters didn’t care about his personal debt.

   During the debates Work promised to cut taxes, reduce the mill rate, bring new jobs and championed fixing sidewalks and potholes ,”because he doesn’t want to lose any teeth” in the potholes.

    Ray Work has fallen on the GOP sword again.

    The biggest development in the local Republican Party in 2019 has nothing to do with Vernon Matthews or Ray Work – it was the decision of alderman Steve Giacomi to not seek re-election. Giacomi is young, articulate and politically ambitious. Many political pundits saw him as the strongest candidate in the GOP to run for mayor, this year, or certainly when O’Leary loosens his grip on City Hall.  Giacomi, however, was wounded by two losses in recent state representative campaigns, and concluded he could not win as a Republican in Waterbury.

Steve Giacomi and his family on election night 2018

    Giacomi announced this summer on WATR that he was through with Waterbury politics and was considering moving outside the city to focus on his wife and two young children. A loss for Waterbury, but a gain in the Giacomi household.

   Keisha Gilliams is a Democrat who found herself boxed out of the process by incumbents. She tried unsuccessfully to run as an alderman in 2017, and decided to run for mayor this year. She was unable to get the necessary number of signatures to force O’Leary into his first primary challenge, but she petitioned herself onto the November 5th ballot as an unaffiliated candidate.

Keisha Gilliams

   Gilliams seemed out of sync at the chamber debate and answered questions from a neighborhood perspective – her neighborhood, and seemed better suited to be an alderman fighting for a better relationship with the police in the city’s North End. She promised at both debates that she was there to cut taxes, but offered no plan to do so.

   The most intriguing challenger is Ty McElrath, a 32-year-old with a huge personality and an infectious smile.  McElrath is African-American and openly says he hasn’t participated in the voting process for years because “I didn’t feel like anyone represented my interests or my voice.”

   McElrath is running a write-in campaign and believes with a vigorous social media effort he can excite millennials and has an outside shot at victory.

   “Obviously I want to win,” McElrath told the Observer as he conducted a pop-up campaign along Lakewood Road in early October, “but my main mission is to get young people to get involved in the process. I will remain active in politics whether I win in November or not.”

Tyler McElrath

   McElrath said if he’d announced he was seeking a position as alderman it would not capture the attention he has garnered by challenging the mayor. His friends sat up and noticed when he announced he was going for the top prize, and young faces were sprinkled through Veterans Hall for his debate appearance.

   During the City Hall debate McElrath called for a resurgence in civic involvement and said everyone needs to play a part. He called for an increase in funding for technology and math and the arts, and said the way our kids learn has changed, and our “curriculum is over 100 years old.”

    McElrath may have little chance of toppling Goliath on Election Day, but his idealism and youth are desperately needed in the political arena in Waterbury. McElrath has positive jolts of energy shooting out of him, and while he provided details for his plans that are mostly unworkable – they were details – and refreshing. And best of all, McElrath is beginning to connect with the youth in the city – his peers – that are totally disengaged.

   So, what does all this mean?  Neil O’Leary will win another four-year term as mayor of Waterbury, but the real drama this municipal election will be if Larry De Pillo can get back on the Board of Aldermen (replacing Giacomi who knocked him out in 2015) and provide a much need pebble in O’Leary’s shoe.

   De Pillo has run for mayor six times and placed his name on the ballot in Waterbury for two straight decades. He has a shot as an Independent Party candidate from the 3rd District. The party has no money, but other than O’Leary, no one in the city has greater name recognition.

   O’Leary is in. Giacomi is out. De Pillo is lurking, and McElrath is infusing a breath of fresh air into Waterbury politics.