December 26, 2005
Eye spy | A conversation with Portland-based private investigator Douglas Calderbank
By Taylor Smith
After seven years as a professional bartender, Douglas Calderbank was looking for a change of venue. He wanted to quit his job at the Top of the East Lounge in the Eastland Park Hotel in Portland, but wasn't sure which direction he wanted to head professionally. One thing Calderbank was sure of is that he didn't want to be tied to an office.
He discovered a unique career path one day at the Top of the East when he met Dana Cunningham, a local private investigator who ran a shop in Portland that worked on insurance fraud and workers' compensation cases. The pair struck up a friendship and Calderbank joined Cunningham in 1999, spending nearly two years apprenticing as a private investigator before joining Cunningham's company as a full-fledged private eye.
Last year, Calderbank opened his own firm, Calderbank Investigations, in Portland and kept working the kinds of cases that Cunningham had trained him on ˆ fraud, workers' comp and other corporate investigative services such as employee background checks. According to David Armstrong, a detective with the Maine State Police who handles private investigator licensing for the Maine Department of Public Safety, that kind of work is the bread and butter of the roughly 240 licensed private eyes in Maine.
Mainebiz recently spoke to Calderbank about the life of a private eye, including successful surveillance tips, the limits of the law and how to deal with an angry guy who just caught you spying on him. An edited transcript of the conversation follows.
Mainebiz: You didn't come into the private investigation field with any kind of law enforcement or military background, as most investigators have. What kinds of tips and tricks did you learn from Dana Cunningham?
Calderbank:I don't think anyone could just jump into this job and do it. Even with the training, a lot of it is common sense and using your own skills. It's street smarts, basically. You have to read people's behavior, and you need to be able to tell if you've pushed it too far.
Following someone around, it all depends on the subject, where they live. If they live in Portland, you can drive by their residence a number of times without getting busted. But if the guy lives in Buxton on a dirt, dead-end road, you have one chance to go down there and view the property and make an assessment. If you drive back down there, you're going to get busted. Common sense is the key; if you don't have it, none of the other tips and tricks will work.
So what kinds of things are you looking for when you're doing surveillance for, say, a workers' comp case?
We're fact finders. We're there to just show a day in the life of the claimant. We might happen to catch them doing something they shouldn't during those two or three days doing surveillance, but we're not there trying to make them do it. We're there to be discrete and not bother them, as well as keeping it undercover until the case can be brought forward to the workers' comp board.
Are there boundaries you can't cross when it comes to surveillance? Do the people you're watching ever know they're being watched?
With [state] stalking laws, if you're harming or bothering the person in a way that they feel fearful for their life, you can [get in trouble]. We're just there as observers. But if we ever have an issue that the claimant knows that we're following them, we'll drop it and pick it up maybe two or three weeks later with a different vehicle and a different investigator. We don't want the police knocking on our door saying this person is asking for a restraining order against you for harassment.
They can do that?
That's within their rights. The judge would have to agree and there needs to be a reason and witnesses and all of that. But it's never come to my attention. I have been busted ˆ it does happen. As good as you are at surveillance, people sometimes are looking out for it or circumstances happen that you're just known.
So have you ever run up against someone who wasn't too happy that you were watching them?
I've been very lucky. I've been in the woods before and have been confronted; I walked away just by talking. I've not been physically harmed or had any problems. I had a case in Windham with a very surveillance-cautious claimant. The guy was finally mowing his lawn and doing some activity and I was driving by with a friend. I told my friend to drop me off. So I got into the woods, but I didn't know that the next-door neighbor noticed me getting dropped off. He contacted the claimant and they both started walking across the street, and my friend had left the area, so other than a cell phone I had no way of getting out of the area.
They both confronted me, and I was in an area where they easily could have done anything. I was able to talk out the situation and told them I'd like to be in view of the busy road, Route 115 in Windham. They said no, and told me that they had called the Windham Police. I was thankful for that. One of the guys claimed that I was watching the kids next door, but that wasn't the case ˆ I had video proof of what I was watching. The Windham PD showed up and they let me talk first. I showed my license, which is issued through the Maine Department of Public Safety, and they let me go.
Close call. So, can you give me an example of a typical case?
The insurance companies usually ask for surveillance because they have some red flags regarding the claimant ˆ maybe [he or she] is working on the side and the insurance company got a tip from the neighbor, or an ex-girlfriend will open up a can of worms. So we get tips or the insurance company just wants to do an activity check and see what's going on for a day or two. The back of my car is full. I have gym clothes, so if the subject or the claimant goes to the gym, I'm prepared. I have beach stuff in the summer if they go to the beach, and in the winter I have full camo winter gear so I can be comfortable sitting buried in the snow or up against a tree for three or four hours getting video. I have my vehicle prepared for whatever kind of situation comes up.
What kind of car do you drive?
Oh, I can't disclose that. It's a sedan. It's boring. I'd love to drive around in a Ferrari like Magnum, but I actually have to have a boring car so people just don't see it. You can't do any markings, you can't do any stickers, you can't put your favorite political candidate on the back. It's got to be just plain Jane.
Where does your work take you?
You might go to the Maine Mall, you might go to the movie theater, you might go to Peaks Island. You drive to Boston, you jump on the Amtrak. Your day is basically what [the subjects] do for the day. You can't say, "Honey, I'll be home at 4:00." Whatever they're doing, you're doing. And the equipment changes as they change what they're doing: If you're just driving around, you can use a normal video camera. And when they're going to a mall or an establishment like Wal-Mart or Home Depot, we have a covert cell phone and a covert pager that clips to the same camera and it doesn't even look like a camera. You can have it right in the cart, or carry it on you; we even have smaller cameras if we get in tighter situations, like a bar.
Do you ever come away empty handed?
Maybe 10%-15% of the time. It happens. Everything depends on the subject being investigated and what they do that day or two, and how much money we can put into that case. If money's not a problem, you usually get a lot more [information]. If you don't have any activity and the subject is not legitimately hurt and not an active person on those two days that you're selected to do the work, then yes, it's disappointing, but you're just there to provide the facts.
Is it always one person doing the work?
The success rate and amount of evidence increases quite a bit with a second investigator, but sometimes we can't afford it if the insurance companies don't want to pay for it. If we're doing a case, we'll usually start off with one man and if we get there and it's real difficult or the situation's best if the investigator is in the woods and there's another investigator down the road, we'll make those recommendations.
What does this kind of work cost?
A background check can cost between $200 and $300, or up to $8,000 for surveillance. It's usually between $5,000 and $6,000.
What was one of the strangest cases you've worked on?
I've driven to Florida from Massachusetts for a workers' comp case. I was working with [Dana] Cunningham at the time, and we sat in the same vehicle for something like 14 hours. We didn't know exactly when [the subjects] were leaving; we just had a tip. They happened to get into an RV and we followed them right down to Florida.
And they didn't notice someone following them for 1,200 miles?
Nope. Not at all. We knew they were leaving around a rough date and going to Disney World in an RV. Sure enough, we followed them and they made two stops ˆ one on the New Jersey Turnpike at the rest area and the next one they stayed with some friends in Georgia. And then they arrived [at Disney].
But the thing was, we had to be very careful because this was right after Sept. 11 and people were very aware of people's behavior. It was interesting. We actually made it a few days before someone called the Disney security on us. People eventually catch on to what you're doing.
What happened with that case?
I don't really know how it ended up. That's one of the problems with this job: We do the investigation or the surveillance, and a lot of times we just don't know the outcome. It's like starting a book and never getting to the last page. That happens 97% of the time. You start a lot of good stuff and you don't know how it ends.
He discovered a unique career path one day at the Top of the East when he met Dana Cunningham, a local private investigator who ran a shop in Portland that worked on insurance fraud and workers' compensation cases. The pair struck up a friendship and Calderbank joined Cunningham in 1999, spending nearly two years apprenticing as a private investigator before joining Cunningham's company as a full-fledged private eye.
Last year, Calderbank opened his own firm, Calderbank Investigations, in Portland and kept working the kinds of cases that Cunningham had trained him on ˆ fraud, workers' comp and other corporate investigative services such as employee background checks. According to David Armstrong, a detective with the Maine State Police who handles private investigator licensing for the Maine Department of Public Safety, that kind of work is the bread and butter of the roughly 240 licensed private eyes in Maine.
Mainebiz recently spoke to Calderbank about the life of a private eye, including successful surveillance tips, the limits of the law and how to deal with an angry guy who just caught you spying on him. An edited transcript of the conversation follows.
Mainebiz: You didn't come into the private investigation field with any kind of law enforcement or military background, as most investigators have. What kinds of tips and tricks did you learn from Dana Cunningham?
Calderbank:I don't think anyone could just jump into this job and do it. Even with the training, a lot of it is common sense and using your own skills. It's street smarts, basically. You have to read people's behavior, and you need to be able to tell if you've pushed it too far.
Following someone around, it all depends on the subject, where they live. If they live in Portland, you can drive by their residence a number of times without getting busted. But if the guy lives in Buxton on a dirt, dead-end road, you have one chance to go down there and view the property and make an assessment. If you drive back down there, you're going to get busted. Common sense is the key; if you don't have it, none of the other tips and tricks will work.
So what kinds of things are you looking for when you're doing surveillance for, say, a workers' comp case?
We're fact finders. We're there to just show a day in the life of the claimant. We might happen to catch them doing something they shouldn't during those two or three days doing surveillance, but we're not there trying to make them do it. We're there to be discrete and not bother them, as well as keeping it undercover until the case can be brought forward to the workers' comp board.
Are there boundaries you can't cross when it comes to surveillance? Do the people you're watching ever know they're being watched?
With [state] stalking laws, if you're harming or bothering the person in a way that they feel fearful for their life, you can [get in trouble]. We're just there as observers. But if we ever have an issue that the claimant knows that we're following them, we'll drop it and pick it up maybe two or three weeks later with a different vehicle and a different investigator. We don't want the police knocking on our door saying this person is asking for a restraining order against you for harassment.
They can do that?
That's within their rights. The judge would have to agree and there needs to be a reason and witnesses and all of that. But it's never come to my attention. I have been busted ˆ it does happen. As good as you are at surveillance, people sometimes are looking out for it or circumstances happen that you're just known.
So have you ever run up against someone who wasn't too happy that you were watching them?
I've been very lucky. I've been in the woods before and have been confronted; I walked away just by talking. I've not been physically harmed or had any problems. I had a case in Windham with a very surveillance-cautious claimant. The guy was finally mowing his lawn and doing some activity and I was driving by with a friend. I told my friend to drop me off. So I got into the woods, but I didn't know that the next-door neighbor noticed me getting dropped off. He contacted the claimant and they both started walking across the street, and my friend had left the area, so other than a cell phone I had no way of getting out of the area.
They both confronted me, and I was in an area where they easily could have done anything. I was able to talk out the situation and told them I'd like to be in view of the busy road, Route 115 in Windham. They said no, and told me that they had called the Windham Police. I was thankful for that. One of the guys claimed that I was watching the kids next door, but that wasn't the case ˆ I had video proof of what I was watching. The Windham PD showed up and they let me talk first. I showed my license, which is issued through the Maine Department of Public Safety, and they let me go.
Close call. So, can you give me an example of a typical case?
The insurance companies usually ask for surveillance because they have some red flags regarding the claimant ˆ maybe [he or she] is working on the side and the insurance company got a tip from the neighbor, or an ex-girlfriend will open up a can of worms. So we get tips or the insurance company just wants to do an activity check and see what's going on for a day or two. The back of my car is full. I have gym clothes, so if the subject or the claimant goes to the gym, I'm prepared. I have beach stuff in the summer if they go to the beach, and in the winter I have full camo winter gear so I can be comfortable sitting buried in the snow or up against a tree for three or four hours getting video. I have my vehicle prepared for whatever kind of situation comes up.
What kind of car do you drive?
Oh, I can't disclose that. It's a sedan. It's boring. I'd love to drive around in a Ferrari like Magnum, but I actually have to have a boring car so people just don't see it. You can't do any markings, you can't do any stickers, you can't put your favorite political candidate on the back. It's got to be just plain Jane.
Where does your work take you?
You might go to the Maine Mall, you might go to the movie theater, you might go to Peaks Island. You drive to Boston, you jump on the Amtrak. Your day is basically what [the subjects] do for the day. You can't say, "Honey, I'll be home at 4:00." Whatever they're doing, you're doing. And the equipment changes as they change what they're doing: If you're just driving around, you can use a normal video camera. And when they're going to a mall or an establishment like Wal-Mart or Home Depot, we have a covert cell phone and a covert pager that clips to the same camera and it doesn't even look like a camera. You can have it right in the cart, or carry it on you; we even have smaller cameras if we get in tighter situations, like a bar.
Do you ever come away empty handed?
Maybe 10%-15% of the time. It happens. Everything depends on the subject being investigated and what they do that day or two, and how much money we can put into that case. If money's not a problem, you usually get a lot more [information]. If you don't have any activity and the subject is not legitimately hurt and not an active person on those two days that you're selected to do the work, then yes, it's disappointing, but you're just there to provide the facts.
Is it always one person doing the work?
The success rate and amount of evidence increases quite a bit with a second investigator, but sometimes we can't afford it if the insurance companies don't want to pay for it. If we're doing a case, we'll usually start off with one man and if we get there and it's real difficult or the situation's best if the investigator is in the woods and there's another investigator down the road, we'll make those recommendations.
What does this kind of work cost?
A background check can cost between $200 and $300, or up to $8,000 for surveillance. It's usually between $5,000 and $6,000.
What was one of the strangest cases you've worked on?
I've driven to Florida from Massachusetts for a workers' comp case. I was working with [Dana] Cunningham at the time, and we sat in the same vehicle for something like 14 hours. We didn't know exactly when [the subjects] were leaving; we just had a tip. They happened to get into an RV and we followed them right down to Florida.
And they didn't notice someone following them for 1,200 miles?
Nope. Not at all. We knew they were leaving around a rough date and going to Disney World in an RV. Sure enough, we followed them and they made two stops ˆ one on the New Jersey Turnpike at the rest area and the next one they stayed with some friends in Georgia. And then they arrived [at Disney].
But the thing was, we had to be very careful because this was right after Sept. 11 and people were very aware of people's behavior. It was interesting. We actually made it a few days before someone called the Disney security on us. People eventually catch on to what you're doing.
What happened with that case?
I don't really know how it ended up. That's one of the problems with this job: We do the investigation or the surveillance, and a lot of times we just don't know the outcome. It's like starting a book and never getting to the last page. That happens 97% of the time. You start a lot of good stuff and you don't know how it ends.
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