Monticello, NY – In recognition of Juneteenth, the Sullivan County Legislature on Thursday recognized the Watson family, led by Monticello native Tommy Watson Sr.
“Especially during times of strife and struggle, it is so important to lift up those who inspire us, and Tommy and his family have inspired many,” stated District 8 Legislator Amanda Ward, who organized the ceremony. “Juneteenth is the perfect opportunity to spread that kind of inspiration, and as Sullivan County’s first African-American legislator, I was pleased to welcome the Watsons to the Legislature’s first official observation of Juneteenth.”
About Tommy Watson Sr.
Tommy L. Watson Sr. was born and raised in Monticello, graduating Monticello High School in 1983. He attended Orange County Community College as a Criminal Justice major but was accepted into the New York State Police academy during his sophomore year, earning his badge in 1987. Assigned to the Ferndale and Wurtsboro barracks, he patrolled as a uniformed trooper until 1990, when he became a training officer for new recruits.
Continually impressing his superiors, Watson consistently received promotions: to the Highway Task Force in 1992, to Investigator in the Bureau of Criminal Investigation in 1994, to the Community Narcotics Enforcement Team in the same year (as Case Agent for Sullivan County), to Senior Investigator in 2003 (supervising hundreds of undercover narcotics operations across the Hudson Valley region).
In 2006, Watson was put in charge of Troop F’s Hudson Valley Gun Investigation Unit, and by 2011, he was overseeing all narcotics and gun investigations in Sullivan, Orange, Ulster and Rockland counties.
He retired in 2013 but was hired the next year to be one of the Sullivan County District Attorney’s Office’s welfare fraud investigators, under former DA and now County Court Judge Jim Farrell. And in 2015, the Orange County District Attorney’s Office snapped him up as a senior investigator, appointing him Co-Commander of the Orange County Drug Task Force, alongside Paul Arteta (who’s now the Orange County Sheriff).
Last year, he was appointed Chief Criminal Investigator for the Orange County DA’s Office (under David Hoovler), supervising the Criminal Investigations Unit, Digital Forensic Unit, Arson & Explosion Unit, and the White Collar Crime Unit, in addition to the Drug Task Force. Ensuring a smooth transition between investigations and prosecution, Watson also serves as the DA’s liaison with local, city, State and Federal law enforcement agencies. In total, he oversees 21 investigators, who with assistant DAs handled over 11,400 cases in 2024.
“Tommy Watson is one of the best investigators I’ve ever worked with in my career in law enforcement, and he is deserving of any award bestowed upon him,” remarked Orange County District Attorney David Hoovler.
“Tommy Watson is a prime example of how determination and hard work will open doors for you in any career you may pursue. I worked with Tommy for many years, and he always had my back, as he did everyone else’s, and I am proud to call Tommy Watson my trusted and dear friend,” added Sullivan County Sheriff Michael Schiff. “It was my honor to be part of Tommy’s personal journey. I was able to witness firsthand how he dealt with people who were under stress, who were grieving, or who were injured. His moral compass always kept him straight, and he always seemed to have the right words and take the appropriate action in any situation.”
A Family of Tenacity and Achievement
“I’ve had a blessed career,” Watson affirms. “Serving in law enforcement has been in my blood a long time, and it hasn’t stopped yet!”
Indeed, Watson’s father Freeman was a part-time officer in the Monticello Police Department in the late ‘60s and early ‘70s, and his son Tommy Jr. works in the Sullivan County Sheriff’s Office. In fact, Watson met his wife, Dora, on the job, as she was a New York State Police investigator herself (now retired).
“Dora had 23 years with the New York State Police, serving in Troop F, the Community Narcotics Team and the Specialized Investigation Unit,” Watson notes. “She’s currently working part-time for the Ulster County Sheriff’s Office.”
Not all of the Watson family has taken a law enforcement path, but they have followed the wisdom of Watson’s grandmother, who was an Alabama schoolteacher in the 1940s and ‘50s.
“Education was always instilled in us,” says Watson, who’s proud of his six other children as well: Ashley, a daycare aide; Kevin, a self-employed DJ; Talon, a security officer; Zayne, a Center for Discovery employee; Leticia, a high school senior; and Mya, a high school freshman.
Leticia is about to graduate and will be attending Dominican University as a psychology major in the fall, where she also has been recruited to play NJCAA Division II basketball. That athleticism has been cultivated by her father, who for two decades has been a fixture on the Sullivan County Board of Basketball Officials (referee) circuit.
“My goal was to move up to refereeing at the college level,” he recalls, “but my daughter started playing basketball, and I didn’t want to miss that!”
Celebrating and Nurturing Diversity
Watson fondly remembers growing up in a thriving, diverse Sullivan County.
“There was very little racism,” he states. “You grew up with everyone of every background.”
He remembers being trained and mentored by Sullivan County Sheriff Michael Schiff back when both were troopers, along with longtime Sheriff’s Deputies Luis Alvarez (now District 6 Legislator) and Roland “Gator” Ward (father of Legislator Amanda Ward). As an African-American man himself, Watson is proud to have inspired and nurtured talent from all walks of life and ethnicities.
“I’ve recruited many minorities into law enforcement, and I know several young minority officers who looked up to me as kids,” he nods. “You have to have equal representation in order to relate with the communities you serve. As an agency, you have to be as diverse as your community is – that’s the way we build bridges.”
And Watson still maintains deep ties to Monticello, where he continues to own a residence.
“It will always be home to me,” he says.
