François McKinnon: Hi there and welcome to the Miami PI Chronicles podcast. I’m your host François McKinnon, the owner of McKinnon Investigative Group in Miami, Florida. I’ve been a private investigator for over 30 years in the South Florida area. McKinnon Investigative Group has taken me to many unique destinations, both domestic and abroad. I’ve conducted complex investigations as well as countless protective details throughout the world. The Miami PI Chronicles podcast will bring you inside the world of private investigations and the security industry. This podcast will showcase different guests who will bring you their professional expertise in their specialty fields and some of their wildest and most memorable cases. Our guests will be from different backgrounds in investigations, security, and everything in between.
On our show today, I have the honor of having Mr. Oscar Santamaria, president of Optimum Investigations. Let’s welcome my dear friend and colleague, Oscar Santamaria. Hey Oscar, welcome and thank you for being on our show.
Oscar Santamaria: Oh, thank you for having me François. It’s great to see you again.
François McKinnon: Maybe tell our audience a little bit about yourself and your agency, Optimum Investigations.
Oscar Santamaria: Sure. I started my career back in 1992. I was an intern at a small insurance defense investigative agency called Chamberlain and Associates. I worked there for approximately two and a half years. In 1995, I opened up my own agency, which I still run to this day. I continue to specialize in insurance defense surveillances. I also dabble in infidelity cases, but most of my work is done through insurance companies and law firms. I do a lot of work for the cruise lines.
François McKinnon: That’s fantastic. So you’ve been doing this for a long time and obviously made a living out of it. I have a bunch of questions for you. I wanted to ask — what’s a typical day? Let’s say Oscar is at home in the evening, getting his gear ready for the next morning, getting up early. Can you walk our audience step-by-step through what you do, how you conduct surveillance, and what happens during a surveillance? Because you and I both know what happens, but a lot of people don’t — they think it’s something fancy like Magnum PI. We’re not following anybody in a red convertible Ferrari. Can you tell us a little bit about your daily experience?
Oscar Santamaria: Sure. I’m a surveillance specialist. What I typically do is the evening before, I study the case. I check addresses and databases, make sure I have the current vehicles and who lives in the house. I typically find out this information either through the client or through a database search. Then I do a Google Maps search and check the street view to see where I can find the best places to conduct the surveillance. Some neighborhoods are more conducive to surveillance than others. Then I just sit and wait. It’s kind of like hunting — you get them in your sights, you wait.
Before COVID, people were usually creatures of habit. Ever since then, there are a lot more people working remotely. There’s not as much routine as there used to be, and not as much activity on the part of claimants.
François McKinnon: That must have been very challenging when everybody started working remotely — because you observe and document the movement of claimants for insurance companies. The bottom line is that you need to physically see them, videotape them, and show it to your client to determine whether they are indeed injured. As we both know, a lot of times they are, and sometimes they’re not. What did you do to get creative?
Oscar Santamaria: COVID definitely posed its challenges. Most of the time people would wake up in the morning, go to their job, maybe drop kids off at school. But COVID changed everything. When claimants did leave, if they lived in an apartment building and didn’t own a vehicle, almost everybody came out wearing masks or gaiters. You couldn’t even tell who was who, and it made things very challenging. Also, having worked for a lot of cruise ships — that industry was essentially shut down.
François McKinnon: What kind of work did you do on cruise ships?
Oscar Santamaria: For passengers and crew members that got injured either on a pleasure craft or on a cruise ship. Most of the work I did was for the cruise lines. A passenger or crew member gets hurt and then they have to go through a whole process. It’s not like regular insurance — this is a whole different ballgame. There’s something called maintenance and cure. A lot of these crew members don’t live in the United States. They have a contract, they go on a boat, they get a per diem and a salary. If they get injured, the cruise line has to put them up in a hotel, cover their medical expenses and living expenses until their contract is over. And then of course there’s the litigation process.
If it was the cruise line’s negligence that caused the injury, a lot of times it becomes a scam. These people come from developing countries and there’s a whole network — if you say you got injured, the rest of your contract you can just be hanging out at a hotel. You see them walking around, riding bikes, or even working another job while supposedly recovering. You just have to make sure they’re actually injured, actually treating where they’re supposed to be, and actually experiencing physical issues because of their injuries.
François McKinnon: Not that glamorous, like people think every time they say “oh, you’re a private investigator, how exciting.” We’ve both been in dangerous situations and also exciting ones. I think that’s what keeps us going as private investigators — but a lot of it is waiting, patience, and trying to outsmart the other side. You always have to think a few steps ahead.
Oscar Santamaria: Since social media, that became a really good tool. I was working a claimant who had a hand injury and I found out through social media that he was a professional radio control boat racer. I found out where the next boat race was, went there, and got him working on his boats — using the remote control with both hands. Nothing was wrong with him. Had I not known he did that, I probably would have missed that opportunity because on many occasions he was very inactive. But he did go to those boat races.
François McKinnon: Because you were proactive. You always did a little digging. It isn’t just going out there — you should always try to find out as much as you can on your subject.
Oscar Santamaria: You get a lot of resources these days. Most professionals will be on LinkedIn, so that tells you a lot. A lot of people share everything on social media and most don’t set their profiles to private. You can actually look into people’s activities all the time. If their profile happens to be private, you look for a spouse, a sibling, a girlfriend, a boyfriend — and usually you’ll find something. But you have to do your digging.
François McKinnon: And as I know, you also run background checks. What kind of information do you get from those?
Oscar Santamaria: You get all sorts of information — criminal records, motor vehicle records, address history, relatives, associates, business ownership, bankruptcy liens and judgments, whether they have a concealed weapons permit, a hunting permit. It’s a really great tool. When I first became a private investigator, the internet was just emerging. You had to pay by the minute back in 1992. By 1995, things were flat rate and everybody started using it. When Facebook first came around, it was a wealth of knowledge. Some social media platforms come and go. A lot of claimants are now advised by their lawyers to set things to private during litigation. People are catching up, but you’ve always got to try to be a step ahead.
François McKinnon: What else do legal counsel tell their clients? To be wary of private investigators?
Oscar Santamaria: There’s definitely times when surveillance opportunities arise around legal proceedings. Before COVID, depositions were done at a specific location. Now they’re often done through Zoom remotely. But when there is a lawsuit, one really good opportunity is when the defense arranges for their doctors to examine the claimant. Those are called CMEs or IMEs — compulsory medical examinations or independent medical examinations. The claimant is required to attend. If they miss it, there’s actually a disruption fee — these doctors charge $2,500 for an exam and you pay it whether you show up or not. That’s a time when investigators will try to follow someone, especially if they don’t have a vehicle or live in a high-rise or gated community that’s otherwise difficult to access.
François McKinnon: Speaking of gated communities — how do you handle those?
Oscar Santamaria: You can use pretexts, like posing as a process server. Sometimes you can piggyback in behind another vehicle. Sometimes you know someone who lives in the same community. Sometimes there are certain gate codes that work automatically. In large gated communities with no guard, you can call a random unit and people will just press the button and let you in without thinking. That’s a form of pretexting.
Pretexting more broadly is when you contact someone to verify they’re home or confirm they’re actually the claimant. You’ll call or knock on the door just to confirm someone is there, because you don’t want to sit on an empty house. Sometimes if you don’t have a photo, you’ll do a witness pretext — you’ll say you’re looking for a John Smith who was a witness to an accident. If they say “my name is John Smith but I never witnessed an accident” — you just go with what you’re presented with.
François McKinnon: Very interesting. Now I wanted to tell our audience that you and I worked together around 1994 for several years as partners. I spoke to you last week before the show and some of the stories that came up were truly incredible. I wanted to share with our audience the case in Dania Beach — the one where we started following the woman who was supposedly not cheating on her husband. Why don’t you pick it up from there?
Oscar Santamaria: We set up surveillance and we had two cars. It was pouring down rain, so I went to talk to you by your car — and the subject departed. I had to jump into your car and we started following her.
François McKinnon: That was a case that came through the father of my brother’s best friend. He gave us a picture of a man, some phone numbers, and told us his wife would go away every weekend and he knew she was having an affair. She had a picture of this guy — he was lying on a bed wearing a cowboy hat. So like clockwork, we were working it on a Friday evening. She left. You were outside your car for some reason.
Oscar Santamaria: Yeah, I came over to talk to you and we just said — jump in, let’s go. You had your wife go pick up your car the next night to get it out of there.
François McKinnon: So we followed her to Lakeland, Florida. We were on her for a while. There was a blinding rainstorm, but thank goodness she had a Buick with distinct rear lights — that’s the only way we could see her from a distance. And your wipers weren’t that great, by the way.
Oscar Santamaria: Probably not. Then she cut through what I thought was a Denny’s or Burger King parking lot. We thought she was stopping to get food, but it turned out to be a cut-through. After being on the road for two and a half hours, we lost her.
François McKinnon: We had a few leads — we knew where her sister lived. Since we didn’t actually know where we were, we stopped to get a map. I asked someone what city we were in. Then we went across the street to a gas station and I walked in and said “what city are we in?” The lady said “you’re in Lakeland.” I said perfect, this is where I need to be. She asked where I wanted to go and I told her honestly — I’m a private investigator from the Miami area and I lost my subject somewhere around here. The woman grabbed me by the hand and said “I know who you’re following.” She wouldn’t let go. I said — lady, I highly doubt that. And she blurted out the subject’s name.
Oscar Santamaria: Now you don’t know what to say. What are the odds? She could be a friend of your subject.
François McKinnon: Exactly. I said no at first, and then I started thinking — wait a second. And then she explained that her boyfriend was having an affair with this same woman. She had actually gone down to South Florida to try to locate the man herself but couldn’t find him. After talking, we told her we’d be at a nearby hotel and invited her to come talk after her shift. She told us everything — the guy’s name, where he’d be. We ordered pizza, got a room at the hotel across the street.
Oscar Santamaria: She came after her shift and we videotaped her on a tripod. She gave us a full recorded statement with everything she knew. And then she said — by the way, I know exactly where they are right now tonight.
François McKinnon: We looked at each other and said, let’s play along. I asked if she’d like to get in the car with us and take us there. And she did. We went to a bar, she stayed in the vehicle, and we went in with covert video cameras. We sat probably ten feet away from them. They were extremely intimate in a public place.
After that, we went back to the hotel and I called the client and told him everything that had happened. We had the subject’s name, the boyfriend’s phone number — which turned out to be a payphone right next to where the boyfriend lived with his brother — the hotel they used every week, everything.
Oscar Santamaria: They went to the same hotel every single week. And sure enough they checked in the next day. We followed them to a bowling alley. We had so much video evidence and conveyed everything to the client — but he said no, I want you to continue. So we stayed.
François McKinnon: One evening they were coming out and she spotted me on the corner. She started yelling and they called the police. The police showed up — we were fully licensed and doing everything legally. She was just trying to cause problems. We were able to move on from there.
The client hired us to go back again a couple of weeks later. He just wanted to know everything she was doing. Every time she left town, she was with this guy.
Oscar Santamaria: She went several times.
François McKinnon: They eventually got divorced. I remember we also had to videotape her leaving the house toward the end to document that there was no violence. It was a wild situation. And that was actually the very first case that we ever did as partners.
Oscar Santamaria: It really was.
François McKinnon: What are the odds of a woman just grabbing you in a gas station and knowing exactly who you’re watching? Astronomical. That case told us — I think we’re off to a good start here.
Oscar Santamaria: We had just started together.
François McKinnon: From my point of view, I was sitting in the car watching the entrance wondering what was taking so long. Then I see her dragging behind you, holding onto your belt or something. And then I heard the subject’s name and I thought — is she friend or foe? It got me nervous. Then I got out and we talked to her and said — come to the hotel after your shift, we’ll have pizza and talk. She was gracious enough to come and give us everything, and clearly she was hurting because her boyfriend was being cheated on every time this woman came to town. If there are PI gods, they were smiling on us that day.
Oscar Santamaria: On that day they definitely were. And folks, this was our very first job as partners. And it didn’t stop there — it just kept going and going.
François McKinnon: We have to tell our audience that locations and certain identifying details have been changed, as professional investigators. Oscar, you are the president of Optimum Investigations. Where are you located?
Oscar Santamaria: We’re in South Florida, in the Fort Lauderdale area. We cover from Key West to Palm Beach, and I’ll go to Naples if I have to. We also have contractors in different parts of the state and country — so if I get a call from one of my cruise ship clients about a case in Iowa, I can network with other investigators, farm it out, and manage it from here. The clients still deal directly with me.
François McKinnon: Same process — observe, document, report back.
Oscar Santamaria: Exactly. It’s really about having common sense and the ability to overcome boredom, because a lot of the time you’re just sitting for hours and hours. You need patience. People don’t get that. It gets extremely hot in South Florida — sitting in a car in 93-degree heat with 106-degree humidity, you can’t run the AC the whole time because someone might notice. You want a quiet engine, nothing that draws attention. And the vehicle really makes a difference. You don’t want a red Ferrari like Magnum PI — that would never work. You want something generic that blends in. Toyotas, Corollas, Camrys, Hyundais, Volkswagens. Neutral colors — white, gray, nothing like yellow or orange. White SUVs are perfect for this type of work.
François McKinnon: Thank you so much Oscar, and let’s have you back on the show soon. To reach Oscar Santamaria at Optimum Investigations, call 1-800-745-4021, visit optimumprivateinvestigators.com, or email [email protected].
Thank you for listening. We’ll see you next time.
This episode is sponsored by The Spy Shops. For all of your investigative needs, visit www.spyshops.com
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