The Chief
07/01/2007

The Chief

By John Murray

   Police Chief Neil O’Leary is the most influential man in Waterbury right now.
In addition to heading a force of 300 armed police officers, O’Leary used his political might in March and April to raise $600,000 to help the Police Athletic League (PAL) purchase St Lucy’s School. The majority of the money came directly from O’Leary’s hands-on fundraising efforts. The impact of the PAL Program under O’Leary’s leadership is staggering.
   When he took the reigns down at police headquarters a few years ago the program was servicing less than 100 Waterbury youth. Under O’Leary’s guidance PAL is now working with 1200 inner city youngsters, and with the purchase of St. Lucy’s, the positive influence of PAL will be felt for generations to come. The extraordinary resurgence in the PAL Program is one of the most positive developments in Waterbury during the past decade. Much of the credit goes to O’Leary, the most intriguing character in the city.
   During the Best of Waterbury readers’ poll in 2006 and 2007 our readers chose Chief O’Leary as a person they would like to see run for mayor. They also gave O’Leary strong consideration as the Most Powerful Man in Waterbury, and for Person of the Year.
   O’Leary was just featured on NBC Dateline as the hero in solving the bizarre Donna Palomba rape case. Palomba credits O’Leary with solving the crime, and changing procedure inside the police department on the way officers handle sexual assault investigations.
   O’Leary was the stand-up figure inside police headquarters in answering questions about the mysterious disappearance of Billy Smolinski. While detectives refused to describe the case as suspicious, O’Leary cut through the fog and declared something bad had happened to Smolinski. O’Leary has also been supportive of Janice Smolinski’s effort to change the law about the missing in Connecticut.
   Clearly Neil O’Leary is on a positive roll right now. Community groups and associations are honoring him for his civic accomplishments, and for his dedication to upgrading investigative techniques inside the Waterbury PD.
   At the moment there seems to be little negative fallout to O’Leary’s strong political posture in the Brass City. That has not always been the case. During the past 16 years O’Leary has demonstrated a remarkable ability to adapt and make political alliances with people in power. In the 1990s – years before he became chief – O’Leary was already considered the most influential and controversial member of the Waterbury Police Department.
   During another time and place, O’Leary’s politics had him embroiled in a string of controversy. We remember some of the war stories not to embarrass the chief, but to celebrate his uncanny ability to land on his feet and keep moving forward. There was a time when it seemed Neil O’Leary would never make it to police chief, let alone raise $600,000 to help inner city kids.
   Consider this; he has been investigated twice by the Chief State’s Attorney office. The first time was for his role in a highly publicized traffic accident in 1995 that involved former police chief Ed Flaherty, a deer, and conflicting stories about who was driving the car. It is widely believed that Flaherty, who had been selected chief that night, was driving the car and O’Leary covered for him.
    The Republican-American newspaper railed against Flaherty and O’Leary, yet an investigation by the Chief State’s Attorney found the evidence inconclusive.
   Five years later O’Leary was investigated by the Chief State’s Attorney for alleged overtime abuse. A letter sent by a fellow police officer accused O’Leary of ringing up 100 hours of overtime while he was allegedly playing golf in Ireland. The investigation petered out and the case was handed off to the Waterbury Oversight Board who recommended better paperwork systems be installed down at headquarters.
   The allegations came at O’Leary hard and fast, but nothing ever stuck. A series of anonymous letters from police officers inside the Waterbury Police Department accused O’Leary and a small band of cops of corruption. Copies of the letters were sent to newspapers, politicians and the F.B.I.
    After receiving three or four of these highly detailed letters, the Observer called for a Grand Jury to be convened to investigate the allegations. Either good hard working men were being subjected to insidious character assassination, or there was a criminal element operating in the Waterbury Police Department. To our knowledge the letters were never investigated. We asked former Mayor Phil Giordano about the letters in 1998 and he said he had looked into it and found the letters to be wild and unsubstantiated, like many vicious rumors in Waterbury.
   The Observer has had an interesting relationship with O’Leary that dates back to 1994 when he was a sergeant in the police force. Mike Bergin was the mayor in Waterbury at that time and O’Leary was his driver and self-described “best friend”. I got to spend election day with O’Leary and Bergin in November 1995 and found the young sergeant to be charming, witty and funny. He still is.
    After Phil Giordano was elected in 1995 one of his first moves was to try and cleanse the police department of Bergin loyalists. Giordano’s first target was Neil O’Leary, who the newly elected mayor suspected of snooping around in his background during the mayoral campaign. One of Bergin’s last moves in office was to get O’Leary assigned to the Statewide Narcotics Task Force and out of harm’s way.
   Giordano ordered Flaherty to reassign O’Leary to patrol and Flaherty refused. In the ensuing showdown Flaherty was fired and temporarily lost his job. Several police officers told the Observer that Flaherty was fiercely loyal to O’Leary because Neil had covered for him in the traffic accident. In the end the only people who know the truth are Ed Flaherty and Neil O’Leary, everything else is supposition.
   One thing that is certain is that Phil Giordano’s target in January 1996 wasn’t Ed Flaherty, it was Neil O’Leary. Flash forward three years to election night 1999. Giordano was in a hotel suite with his wife and kids, his parents, his sister, and ten to twelve close campaign workers. The returns started filtering in and there was a knock on the door. It was Neil O’Leary, who was now welcomed into Giordano’s inner sanctum.
   And that’s part of the magic of Neil O’Leary. A few years before he was Mike Bergin’s best friend and Giordano’s #1 enemy. Then on a cold night in 1999 he was still Mike Bergin’s best friend, and Giordano’s ally as well.
   And amazingly, O’Leary has now forged a strong relationship with the Republican-American newspaper and it’s publisher Bill Pape. The daily paper has helped promote the PAL Program and Mr. Pape and his executive editor, Jonathon Kellogg, have been invited to the public events to join O’Leary and other distinguished dignitaries on stage.
   To watch Neil O’Leary and Bill Pape chat and laugh together is astonishing for anybody who lived through the blood bath that was the Waterbury municipal election of 1995. Again, it’s Neil O’Leary working his magic, building bridges across rifts and canyons that seem too far and wide to heal.
   It’s why he is the most influential man in Waterbury.

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