O’Leary Clobbers Four Challengers

      Neil O’Leary launched his inaugural campaign for mayor on February 6th 2011 inside a dilapidated store front on East Main Street in downtown Waterbury. At the end of his speech O’Leary sang along to Petula Clark’s “Downtown”, and he appeared to be having the time of his life. Flash forward to election night 2019 and many of the same O’Leary supporters stood in a different empty storefront in downtown Waterbury, this time on Bank Street. After O’Leary snared 69% of the votes in a five-way race for mayor he strode to the microphone as “Downtown” blared again through the speakers.

   O’Leary was fired up after winning his 4th term as Waterbury mayor and implored the crowd to join him in singing. Some did, but many in the room simply clapped and cheered another Election Day win. Eight years ago the song represented hope and imagination as O’Leary made downtown revitalization the centerpiece of his campaign.

   Much has happened since that frigid Winter afternoon in 2011, and it turned out revitalizing downtown turned out to be more like running a marathon than 100-yard dash.

   O’Leary spent much of his first year in office facilitating a proposed merger between St. Mary’s Hospital and Waterbury Hospital, and the construction of a $500 million state of the art hospital in downtown. The merger and new hospital were described as a “opportunity that comes along once every 50 years”, but the project was thwarted in the 11th hour by the Catholic Church’s unwavering opposition to abortion.

   Portions of state money pledged to the hospital merger was eventually redirected to the revitalization of the 120,000 square foot Howland-Hughes Building on Bank Street. O’Leary announced the project in a joint press conference with Governor Dan Malloy in the summer of 2014, but it took three years of wrangling with Green Hub Development, Post University and Hank Paine (the principal owner of Howland-Hughes) to close the deal. After a year of renovations Post University opened a hub inside the Howland-Hughes building, a move that has delivered 500 employees into the heart of downtown.

   So far it’s been Neil O’Leary’s signature downtown moment, but there have been others.

   The Green went through a massive overhaul in 2017 and 2018 and now has improved walkways, benches, electrical hook-ups and free wi-fi.

   East Main Street from the Green to the Waterbury police station will be repaved and bright lights will be installed in this critical artery that includes Waterbury UConn, the Palace Theater and the Waterbury Magnet Arts School. Work is underway now.

   Green Hub Developers built modern dorm space in the Lombard Building at the corner of East Main Street and South Main Street, and O’Leary and his economic development team played a critical role in making that happen.

   Bringing more students downtown is a goal of the O’Leary administration, and a third Green Hub Development project at 36 North Main Street might accelerate that prospect.

   In 2013 the mayor was appalled at the entrance to the Silas Bronson Library and ordered hedges removed and the entrance opened up to be more inviting. There is now a fountain at the entrance and public art on the lawn leading into the library.

   In the Autumn of 2012 the mayor attended a city planning conference in Pittsburg and urban experts looked over maps of Waterbury and identified Library Park as an underutilized asset. O’Leary returned to the city determined to focus on Library Park and his administration has been essential in creating The Gathering and the Waterbury Jazz Fest. Partnering with the Rod Dixon Kids Marathon in 2012 brought thousands of students into downtown Waterbury to run a mile along city streets and end in a celebration inside Library Park.

   Library Park is closed now as it undergoes a massive renovation and when the project is finished (most likely in 2021) it will be better equipped to handle bigger festivals and will continue to be a community centerpiece.

   Public art has popped up during O’Leary’s time in City Hall creating a transformative visual change in downtown Waterbury. A fish mosaic of tiles called “Cool Waters” was installed on the side of a building on South Main Street in June 2012, a “Greetings From Waterbury” mural was created in 2016 followed by five Calder-inspired sculptures in 2018.

   And then there is Freight Street.

   Six years ago O’Leary stood in a sun-splashed Library Park and announced that the city had received a $15 million TIGER Grant to begin a massive revitalization project of the Freight Street corridor.

   He called it the “aha moment” of his administration and said the impact would create a whole new section of downtown nestled between I-84, Route 8, the Naugatuck River and a transportation hub located at the city’s iconic train station. The money was from the U.S. Department of Transportation’s TIGER grant program, and the $15 million was believed to be an initial installment.

   “Once the Feds invest in a project,” O’Leary said at the time, “they usually keep funding it until completion. This is a game changer.”

   And the demolition of the former Anaconda Brass factory will begin soon on Freight Street, the Jackson Street extension will punch through Freight Street and onto West Main Street.

   There are also big changes at the railroad station on Meadow Street. State funding helped take down the old SNET Building that blocked portions of the train station parking lot, providing increased visibility and volume.

   “The parking lot will be paved this year and we’ll have cameras and lighting installed,” O’Leary said. “It will be a significant step forward.”

   The rail line between Waterbury and Bridgeport is getting upgraded and rail service will increase in and out of the city. CT DOT is negotiating with the Pape Family (owners of the Rep-Am newspaper and the train station) to lease the south side of the building to create a train station that would provide shelter from the elements and offer coffee and snacks.

   A swing around the corner onto Freight Street and change is visible, with even more dramatic ones scheduled to begin in 2019. The first step in the TIGER grant project was to dig up Freight Street and install new utilities.

   “We have new electric, gas, sewer, water and lighting along Freight Street now,” O’Leary said. “And we built a bike trail that will connect with the greenway we are building along the Naugatuck River.”

   The significance of the massive utility upgrade is that the corridor is now prepared to handle whatever development comes along in the years ahead.



When you take a hard look at the past eight years with Neil O’Leary at the helm of City Hall there is no denying he has made significant strides in downtown Waterbury. It hasn’t been easy, or as quick as he had wished, but O’Leary has earned the right to belt out “Downtown”


“When the process is complete we’ll have 20 acres in downtown Waterbury that will be flat with utilities in place for any project that wants to develop there.”
  O’Leary said progress has been incremental and much slower than he hoped for, “but we’re light years ahead of where we were. We’ve had more progress on Freight Street in the last five years that we had in the previous 50 years.”





In addition to being the mayor of the 5th largest city in the state, O’Leary is the president of the Connecticut Conference of Municipalities (comprised of 168 elected officials from towns and cities in Connecticut), and is the chairman of the 19-town Naugatuck Valley Council of Governments. That is an extraordinary amount of influence locally, regionally and across the state of Connecticut.