2017-02-24 / Front Page

10 questions with Steven Webster

By Wm. Duke Harrington
Staff Writer

Former South Portland Police Department Detective Sgt. Steven Webster prior to his retirement after nearly 30 years protecting the people of Maine’s fourth-largest city. (Courtesy photo)Former South Portland Police Department Detective Sgt. Steven Webster prior to his retirement after nearly 30 years protecting the people of Maine’s fourth-largest city. (Courtesy photo)SOUTH PORTLAND — Former South Portland Police Department Detective Sgt. Steven Webster doesn’t like to give up too much personal information – he’s in his early 50s, and lives in the greater Portland area, is as detailed as he’ll get. The reason? “There are still some really bad people who don’t like me too much,” he says. And it’s not surprising why.

This past month, Webster retired after nearly 30 years on the job protecting the people and places of Maine’s fourth-largest city.

Raised in southern Maine, Webster earned a bachelors degree in criminal justice and a masters in leadership. After joining South Portland Police Department as a beat cop in 1987, he made detective a decade later and spent three years in that position until assigned to the Maine Drug Enforcement Agency in early 2000. Webster spent almost six years with MDEA and returned to South Portland in 2005, earning a promotion to sergeant. Following a brief stint as a patrol supervisor, he became a detective sergeant in 2006, and remained in that position until retiring in January to become global physical security and safety manager for WEX, Inc.


Steven Webster near the beginning of his law enforcement career as a young patrol officer in 1987. (Courtesy photo) Steven Webster near the beginning of his law enforcement career as a young patrol officer in 1987. (Courtesy photo) In 2012, Webster published a book about his experiences battling bad guys, titled “One Promise Kept,” in reference to a vow he once made to a 7-year-old crime victim.

Now, the fight for justice is over, at least with a badge on his chest. On Sunday, Feb. 19, Webster called it a career, surrounded by friends, family and colleagues with a retirement party held at the Italian Heritage Center in Portland.

On Tuesday, Webster took time out from his new post to talk to the Sentry about his life and career spent in service to South Portland.

Q: Who was your boyhood hero?

A: My dad retired from the Portland Fire Department in 1986 and he was the first fulltime fire chief in Cape Elizabeth. He was, and always will be, my hero, though he passed away too young in 1992.

Q: When did you first know you wanted to be a police officer and what sent you down that path?

A: I joined the Army when I graduated high school because I didn’t know what I wanted to get out of life. I was serving in Germany when I read a few paragraphs in a criminal justice textbook that a fellow soldier had. That was pretty much it – I called my folks and they found that Southern Maine Community College (then Southern Maine Vocational Technical Institute) offered an associate’s degree in criminal justice. I worked full time and went to school full time and graduated in 1987. I was hired by the South Portland Police Department right after that.

Q: Do you have any anecdotes about the most interesting or spectacular thing that happened to you during your career?

A: I enjoyed a very colorful and fulfilling career. It is tough to pinpoint one particular case that brought all of my dreams to one place. I did investigate an armed home invasion when I was a brand new detective. The victims were young girls, and I never thought I would solve that case. I received a lot of help from neighboring and federal agencies, and we were able to charge five people federally. We gave those young girls the justice they deserved and I was able to keep a promise that I made the day of the robbery. I told the girls I would catch whoever did that to them (stupidly), and it actually happened. There were so many funny, sad, interesting, weird and memorable cases that I played some role in, that picking just one is a real challenge.

Q: How did the job of being a police office change the most during your career?

A: The law enforcement profession has changed considerably since I began in 1987. I used to actually write my reports while sitting in a cruiser. The newer officers have no need for a pencil because technology has advanced the profession to the point where everything has become computerized. A supervisor used to do what spellcheck now does. Police officers used to carry with them a modicum of respect, but now they’re challenged, questioned and criticized on a regular basis. There are many who still respect authority that is designed to keep them safe, but many others openly question that authority and challenge others to do the same. The officers serving today serve in a fishbowl, and they’re expected to make split second decisions that are scrutinized frame by frame for hours. It is an honorable job that is seeing fewer applicants, due in large part to the low pay, high risk and lessening administrative or political support. The job has changed so much and continues to do so daily. I guess it just got to the point where I couldn’t or wouldn’t accept or keep up with the changes.

Q: How did South Portland change most during your career?

A: South Portland is a great community, but it, too, has changed a lot over the years. The demographics have changed and cultural differences made the job a bit more challenging at times – not better or worse, just challenging. Many people don’t realize that the city has a sleeping population of approximately 25,000 residents, but there can be up to 100,000 during the day with all the businesses on the west end. Not only has South Portland changed, but society as a whole has changed. Many people and criminals are more mobile now and willing to commit crimes in several different jurisdictions instead of sticking to their own back yard, per se. I used to witness kids fighting and a lot of so-called petty crimes. Present day brings the city more violent drug-related crimes, regular overdoses, and all of the crimes that a larger city experiences and is expected to have.

Q: You spend a good portion of your career in drug enforcement. Why did you want to get into that line and what was your biggest or most satisfying bust?

A: I really enjoyed doing drug work, and my fellow agents were among the most dedicated I had the privilege of working with. It takes a special breed to do that work. My goal was always to put the greedy drug dealers (who, it’s worth noting, didn’t use drugs) in prison, while trying to get the addicts help. It didn’t happen often enough, but seeing someone beat their addiction through hard work and dedication was much better than placing handcuffs on a dealer, though that was gratifying as well. There was a time that several agents executed a search warrant near Brackett Street in Portland, and when the investigation finally ended, we seized several pounds of cocaine and almost $140,000 in cash. That case was one hell of a ride.

Q: What in your experience does it actually take to be a successful police officer and how does the actual job differ most from the way it’s portrayed in the media?

A: TV portrays officers in a light that isn’t always realistic. I have never met a cop who wanted to shoot or harm another human being. Most simply want to do their job and help others. Cops are like anyone else, and they’re all different. The job can be extremely stressful and most cases aren’t solved in 60 minutes (including commercials).

Q: Why retire now and what are your post-retirement plans?

A: I retired because I was tired. I’d like to think that I left little on the table when I walked out of the police department on my last day. I had a great career, but law enforcement is a young person’s game, and I’m not as young as I once was. I had the ability to work side by side with some amazing local, county, state and federal officers over the years, but I always felt that I would know when it was time to move on, and I simply knew. I was offered a great opportunity by WEX Inc., a global company headquartered in South Portland, and look forward to learning new things and enhancing an already amazing company.

Q: Anything you’d like to say to the people of South Portland, who you served for so long?

A: I have often said that no one person can save the world, but perhaps we could save one person. I have no regrets and I will always carry a piece of South Portland with me regardless of where my journey takes me. It is an amazing community and it remains in great hands with an exceptional police department.

Q: What advice do you have for young people out there considering a career in law enforcement?

A: I believe that those striving to enter law enforcement should be prepared to have very thick skin, and expect their careers to be pretty much an open book. Again, the times are changing and the officers have to be smarter, wiser, more mature and willing to face scrutiny like never before. I’m hopeful that there are enough folks willing to face that challenge without departments having to lower the hiring standards.

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