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My First Undercover Mission - Success, Fear, and a Pitbull

michaelcdelapena

A check-cashing business
A check-cashing business

THE SECOND MEETING


I lay in the backseat of my FBI undercover Ford Bronco, staring at the ceiling, a sharp pain shooting through my chest. My breathing was shallow but controlled. I knew I had to defeat the pain. I was only 35 years old. Was I having a heart attack? As the Bronco sped through the bouncy streets of Boston, my partner Jen at the wheel, I had only one thought. Don’t let the team down.


I looked forward and saw my partner Jen glancing back at me, a worried look on her face.


“Are you going to be okay?” 


“Yeah, it’s just something we ate at lunch.” I grabbed at my chest as it tightened further.


 “We’ll see,” she said, unconvinced. 


“How much farther?” I whispered.


“We’re almost at the zoo.” 


Boston’s Franklin Park zoo parking lot. The place where the team would be waiting for me. To wire me up. To prep me for the next meeting. I had to get better. I had mentioned what had happened at the first meeting, but they brushed it off. Don’t make it an issue, I thought. Don’t let the team down. I knew I only had a couple of minutes to pull myself together. I couldn’t let the team see me like this. 


A minute later, and after one skillfully executed quick turn, Jen delivered us into the parking lot and the waiting team. 



SEVERAL WEEKS  EARLIER


In the summer of 1998, I had just received my transfer order to the Boston office of the FBI, after having served six years in San Juan, Puerto Rico with the Bureau. The FBI offers any agent who serves five years or more in San Juan a transfer to any office of his or her choosing. I chose the city of my birth. My parents were retired in the Boston area and were also eager to see me and my family. My only trepidation was that I was informed that I would be assigned to the FBI drug squad, a criminal violation with which I had no experience. I wasn’t surprised with my selection to work narcotics, as I was a fluent Spanish speaker. It is commonly known that the drug trade is run from drug cartels in Latin America, who in turn recruit Latinos in the U.S. to sell their deadly merchandise.


I learned upon my arrival on the squad that there was only one other FBI Agent who was a Spanish speaker on the squad. Everyone else was white. There just weren't many Latinos in the Boston FBI office. Despite my concerns, I was determined to learn from my squadmates and do the best I could. For the first few weeks, I grew concerned because the squad was broken down into teams of two and nobody seemed interested in letting me join their crew. I was the odd man out. When one of the teams wanted my help with something requiring my language skills, they would call me and I would do whatever they needed. I was still looking to make my mark when something fortuitous happened.


I learned that the squad was getting a new agent from the FBI Academy at Quantico, Jen Berry. I quickly found out that she had previously worked in the Boston office in another support capacity and had been selected for new agent training. Most amazing of all, upon completing her new agent training, she was allowed to return to Boston, something which the Bureau rarely did. Most interesting of all, she was a fluent Spanish speaker. Once I met her, we hit it off immediately, and in short order started working together, developing informants and building cases. 


Not long after we started collaborating, another agent on the squad approached me about helping him on a case by working in an undercover capacity. He assured me that it would only be a few meetings and it wouldn’t take too much of my time. I didn’t want to let my squad down, so I quickly agreed. At the time, I really didn’t know what I was getting myself into. 


The Boston FBI office had a senior agent named Michael McGowan who was in charge of the undercover program. His job was to make sure undercover assignments didn’t put agents in undue danger and that all aspects of FBI policies were followed. He also made sure that agents weren’t pressured into an undercover assignment. He had a chat with me, informing me that taking the undercover role was purely voluntary. He also stated that he would be monitoring my assignment, as an advisor and mentor. Agent McGowan also assured me that at some point either during or after this operation, he would do everything he could to send me to the FBI’s Undercover (UC) School at the FBI Academy. The Undercover School was a coveted training program and I looked forward to that. 


I appreciated the help as well as the offer of undercover training. Nevertheless, being a bit cocky by nature, and not having any UC experience, I didn’t know what the big deal was. I would soon learn. 


In almost all undercover assignments, the undercover FBI Agent is introduced to the target of an investigation by an FBI informant, also known as Confidential Informant, or CI for short. It is always preferable to transfer all remaining contact with the target from an informant to an FBI undercover agent for a simple reason: The informant almost always has a criminal history and is not as reliable a witness as an FBI Agent, especially if the case were to go to trial. 


In this case, the CI I was introduced to was Carlos from the Dominican Republic, who had developed a brief relationship with the target of the investigation.


I met Carlos near the FBI office. For obvious reasons, it was always preferable for a CI to never be seen entering an FBI office or police station. He was in his early 30s, just a couple of years younger than me. I remember that he seemed respectful and well put together, not someone that would scream drug dealer. He did have prior drug offenses, but he had agreed to work with the FBI. Typically, a CI will work for the government in order to reduce his charges on a pending case against him. Every CI is managed by an FBI handler, who makes sure the CI follows procedures and stays out of any more trouble. The handler is also responsible for writing any reports regarding the CI and paying him as well. They don’t work for free. I trusted his handler, an agent named John, to know what he was doing and to have done due diligence with regard to checking out Carlos. 


They laid out the scenario at that first briefing with me and it was simple. An elderly Dominican man in his 60s named Armando owned a check cashing business on Blue Hill Avenue in Dorchester, Boston. The neighborhood was an area with high crime, which was evident to me the moment we went on a “drive-by” to show me where the business was located and give me the lay of the land. The business was gray, with some graffiti partially scrawled next to the entryway door. The store next door was abandoned, with a “For Sale” sign on a window. This was not a place to be walking around aimlessly. I knew that when the time came, I would want to park near the entrance, and be in and out as quickly as possible. 


What is the point of a check cashing business? A lot of businesses hire employees who do not  have bank accounts. This was more prevalent at the time (1990s and 2000s), prior to the use of smartphones and payment apps that come with them. Workers who don’t have bank accounts may be in the U.S. illegally, lacking the proper documentation to open an account. In some cases, they often give their employers fake names and false IDs because they don’t have papers. Others are poor and don’t have sufficient minimum funds to open an account. Many banks have stringent rules because of oversight by the U.S. government. As a result, an employee receiving a work check has to use a check cashing business to get their funds. The business (Armando in this case), took a percentage of the value of the check. On a $1,000 check, he might take as much as $50. Many of these check cashing businesses prey on the poor who have nowhere else to turn. 


Given that such a business deals with a lot of cash, they are often used by drug dealers to “launder” their money. Drug dealers have to find a way to deposit their money into banks without drawing suspicion. They can’t routinely walk into a bank with thousands of dollars of cash. In fact, banks are required to submit a Suspicious Activity Report (SAR) to the government on any cash deposits of more than $10,000. They must also submit an SAR if it appears a depositor is attempting to structure large amounts in smaller sums. For example, a depositor who brings in $8,000 in cash and then the next day brings in the same amount. 


The solution for many drug dealers is to turn to these check cashing businesses, like the one run by Armando. They bring the business cash and walk out with a check, minus the owner’s commission. That check can then be deposited in a bank without suspicion. During my briefing, Carlos explained that he had met Armando twice, each time giving him $5,000  in cash and leaving with a check for $4,750 (a 5 percent commission). The plan, according to John (the case agent), was for Carlos to introduce me as “the boss,” who wanted to bring in more cash. Armando had indicated to Carlos that more money meant a bigger commission, perhaps 8 percent. I was assigned to negotiate. 



THE FIRST MEETING


Every undercover meeting is preceded by a briefing, where the UC agent is supplied with a hidden microphone (or camera) and a transmitter. Today, those are essentially the same thing. In the 1990s, the microphone only recorded conversations and did not transmit them. Thus the need for a transmitter, so that the FBI team covering the meeting could hear me and (in theory) rush to the rescue if the UC (me) was in danger. A codeword is agreed upon by the UC and the team. I don’t remember the codeword selected, but it was usually something like “hungry” or “I’m hungry.” This was only to be used if the UC (me) felt he needed rescuing. Frivolous use of the codeword would compromise the case. 


My partner Jen and I met the team at the Franklin Park Zoo parking lot in Boston, not too far from the target location. John, the case agent, was there, as well as the UC coordinator, Michael McGowan. Several other FBI agents from my squad were also there to help with the surveillance during the meeting. I was handed the microphone and transmitter and found a place to hide them on my person. 


The decision to take a weapon into an undercover meeting is made by the UC Agent (me) in consultation with the case agent. The threat level inside the target location was deemed to be low based on the information provided by the CI, who had been in the business previously. Further, I didn’t want to be preoccupied with a weapon and the chance it could be seen. I felt it would be a distraction, so I chose to attend the meeting unarmed. 


John pulled me aside with some final words. 


“Remember, this is just a get-to-know-you meeting. You won’t have money, so nobody is going to rob you. A success is having him agree to another meeting where you will bring more cash.” 


“Got it.” 


Carlos seemed very confident in himself as I finished with John and walked over to him. I remember thinking that he was very comfortable probably because he lived in the neighborhood. He fit in. I didn’t. 


“Are you ready?” he asked, looking me over.  


“Is there anything else I should know before we go in?” 


“When we go in, there is bulletproof glass. He is expecting us. I told him you are Miguel and the boss. He will buzz us in and let us into his office. Remember, he doesn’t speak English.” 


“Is there any security person that might pat me down?” I asked. 


He smirked a bit, hesitating. I waited for an answer. 


“He has a dog. A pitbull. He won’t bother you.” 


I said nothing, but thought, yeah right. At least I didn’t have to worry about the dog finding my transmitter. 


Carlos got in my UC car and Jen joined John and the team. He had a transmitter and would be listening to the meeting. Jen would be translating for them. I drove to the business a couple of miles down the road, finding a spot right outside. We walked in and I noticed the bulletproof glass, just as described. Armando, the target, was sitting behind the glass. He had another employee sitting next to him. The dog was at his feet, sleeping. Carlos waved to him, and Armando buzzed us in. 


There were two empty seats next to Armando, and he waved us to sit down. The pitbull got up from his slumber and walked over to me, parking himself directly in front of my balls. He started growling. 


“I don’t think the dog likes me,” I said, forcing a smile. 


“Never mind him,” Armando said calmly. 


“This was my associate Miguel I had mentioned,” Carlos started. 


I couldn’t help but frown. I was supposed to be his boss. That was the whole point. I let it go for now. We would discuss this at the debrief after. 


“Nice to meet you,” I started. 


“Yes, Carlos told me you wanted to bring more cash.” 


He wasn’t in for small talk. I appreciated this, especially since the dog was now growling at me, staring at my private parts. I always think about the worst case scenario in dangerous situations. In this case, I thought in the worst case, the dog might rip my balls apart. Still, I already had three kids and I didn’t want any more. I forced myself to get back to the conversation. 


“Yeah, I need you to take $10,000 at the next meeting,” I offered, looking down at his menacing dog. 


“Okay, but I have to go up to 8 percent. More cash, more risk” he said flatly. 


With every passing moment, the dog seemed to be inching closer and he was growling. I wanted to get out of there. 


“No, too high” I said, “How about 6 percent?”


“Okay, I can go to 7 percent,” he said, irritated. 


“Do you want to put me out of business?” I joked, “I can’t go above 6 percent. Maybe I can go up later, but not now.” 


The dog growled louder. I felt like he was being used as a negotiation tool. I looked at Armando, hoping he would agree. 


“Bueno,” he finally said, much to my relief. He waved as if to signal this meeting was over. 


I wasted no time. I got up and signaled to Carlos, let’s get the hell out of here. 


We walked out to the street and I was grateful to still have my groin intact. 


We drove to the zoo parking lot to meet the team and debrief them on what happened. On the way there, I reminded Carlos that I was supposed to be the boss. 


“Okay, jefe,” he smiled. 


When we got to the location, all of the cars seemed to arrive at the same time. We stood in a circle and I told them how it went down. They heard some of the conversation from the transmitter, but the reception was often poor. They were happy with the outcome. My first undercover meeting was a success, mostly because the stage was set for me to return and meet Armando by myself. 


After the quick debrief, Agent McGowan pulled me aside. 


“Did you have any problems in there?” he inquired. 


“Yeah, he has a pitbull which was growling at me the whole time. I feel like if the old man were to snap his finger, the dog would tear me to shreds.” I was hoping for words of encouragement. 


“Well, just don’t set the dog off,” he advised. Gee thanks, I thought. 


On the drive back to the office, I told Jen about my issue with the pitbull. She looked worried, but what could she say? 


Nobody knew how truly scared I was of that animal. I was dreading a return to that hellhole.  



THE SECOND MEETING (CONTINUED)


Once we pulled into a parking space at the zoo, I was still lying in the back seat. She told me the team was there. Waiting for us. One advantage of being the UC Agent was that they couldn’t start the meeting without me. 


She looked back at me and I was white as a ghost. 


“Should I drive off?” 


“No,” I’m alright, I said, sitting up in the seat. 


Just as quickly as the pain had begun, it subsided. 


I joined the team, slapping my hands together, feigning excitement about the upcoming meeting. In truth, I would have rather done anything else in the world. This time, in addition to the recording equipment and the transmitter, John had me sign a receipt for the $10,000 dollars in cash that he handed me. We counted it together to make sure it was all there. So now on top of the dog concern, I had to worry about not being robbed as I walked to the business. Hopefully, I could get a parking spot just out front like before. If not, at least the team would be watching me as I entered. 


John had a final request for me. 


“Mike, it’s important that he believes this is drug money. Get him into a conversation about how you’re a drug dealer. We don’t want him to later claim that he didn’t know.” 


“Yeah, I know,” I said, “I’ll bring it up.” 


“Alright,” he said, “good luck.” 


I drove to the check cashing business, this time without Carlos. I was grateful that once again, there was a parking spot a few feet from the entrance. When I entered, Armando was dealing with another customer, so I had to wait my turn. When he saw me, I waved and he nodded, acknowledging that he recognized me. He buzzed me in. 


He waved me to an empty seat, and again his dog parked himself at my feet. The growling began. I just wanted this to be over. 


“I have the cash. We had agreed on 6 percent, right?” I started. 


“Correcto,” he answered. 


I took out the bag with the cash and handed it over. He motioned to an elderly lady (his wife?) who took the cash and started counting it, using a cash counting machine. He sat impassively as she did this. Just then, a group of four young Latinos came into the business, and they looked like trouble. At that moment, I made two mistakes. The first was looking at them through the bulletproof glass window. The second was the way I looked at them. I must have given them a “cop” stare. They didn’t like it. 


“What are you looking at bitch!” one of them screamed. I assumed he was their leader. 


“Yeah bitch,” another shouted, banging on the glass. “Come out from behind that glass!” 


My first thought was the case could be in jeopardy. I was concerned that if the team heard this on their receiver, they would come in to “rescue” me and ruin the case against Armando. As badly as I didn’t want to be there, I didn’t want to screw up the case because of my mistake. These were my thoughts as the group on the other side of the glass got louder and more obnoxious. As they grew more threatening, so did the dog, growling inches from my groin. Further, if things escalated, I was unarmed. 


What should I do? Then I had a thought. I turned to Armando. 


Oye,” I said to him, “are you going to let these kids take over your lobby?” 


Armando thought for a moment, then turned to them. 


“Basta!” (Enough!) he yelled at them, waving them away. 


Miraculously, they walked out. I had dodged a bullet. Now I just had the dog to deal with. 


After they left, all I could think was that they would be waiting for me outside the business. This could still ruin the case. I would just have to be watchful when I left. If I left. The dog was still in my business. 


I turned to Armando and he was scrutinizing me. Did he know what I was thinking? Did I give myself away? 


“I’ll need your name for the check. Do you have an ID?” he asked.


I felt a wave of relief at the question. 


“Si,” I said, handing him my undercover driver’s license. The name on the license read MICHAEL DANTE. 


“I thought your name was Miguel?” he asked, suspiciously.


“Everyone calls me Miguel, but it’s legally Michael,” I answered in Spanish… I had been ready for that question. 


“Okay,” he said, walking to the back office.  


After a few minutes, which seemed like hours, he came out of the office with a check for $9,400 made out to Michael Dante. 


In just a few minutes, he had made $600. I’m sure he was very happy, and more than willing to overlook any lingering suspicions. 


“Okay, gracias,” I said, standing. 


As I stood, the dog approached me in a threatening manner. It looked ready to lunge. 


Armando snapped his fingers and the dog sat down. I blew a sigh of relief and walked out the door and into the lobby. I peeked out the window at the street, looking for any signs of the hooligans. They seemed to be gone. 


I quickly walked to my car and drove off. 


Back at the zoo parking lot, the team was already waiting for me. John was with my partner Jen and they approached me first. 


“How did it go?” John asked. 


“Here is the check,” I replied, handing it over. 


“Great,” he said, “did you remember to bring up that you’re a drug dealer?” 


“Shit,” I declared, “I forgot because of what happened in there!” 


I then explained about the hooligans in the business and what had happened. 


“Well, you’ll just have to bring it up next time,” he said flatly. 


“Next time?” I frowned. 


“Yeah, you have to bring this up before we can charge him.” 


“Fuck,” I muttered, “Okay,” 


I dreaded having to go back. 



THE THIRD MEETING


The third meeting was scheduled a week later, by Carlos calling Armando and telling him that his boss (me) wanted to exchange another $10,000 in cash. The afternoon meeting was right after lunch. Jen and I had eaten a sandwich at a restaurant in South Boston, after which we headed over to the zoo again. 


On the way there, I again started having chest pains. I had Jen pull over and I lay in the back seat. 


“It must be something I ate.” I said.


“I don’t think so, Mike.” She said, looking worried. 


“It has to be,” I shook my head. 


“We eat there all the time,” Jen raised a suspicious eyebrow. 


“Don’t worry, just drive,” I replied. I leaned against the door, which helped relieve some of the pain. By the time we approached the zoo, the pain had subsided. 


We joined the team waiting for us in the parking lot. John spoke first. 


“Mike, the most important thing today is to be clear with him that you are a drug dealer. Nothing else matters,” he said seriously. 


“I got it, don’t worry.” 


“Be careful,” Jen said as I jumped into my undercover car. 


On this occasion, there was no parking available right outside the business. I parked a block away, scanned the area for any danger, then briskly walked to the business. As I did so, I noticed one of the surveillance vehicles, which made me feel better. 


I entered, and this time there was nobody in the lobby. He saw me immediately and waved me to the door as he buzzed me into the back. My first thought was that he was eager to make a quick $600. As they say, money talks. As expected, his pitbull was resting next to the visitor’s chair. I sat, and amazingly the dog stayed resting. Could he be getting used to me? 


Armando confirmed my suspicions when he went right into the business at hand. 


“Do you have the money?” he asked, smiling. 


“Of course,” I answered, handing over the envelope with the money. He called out to someone, and the elderly female from before emerged from a back room. She pulled a money counting machine out of a drawer and started slipping the bills in. I knew this was my chance to bring up what could be an awkward topic. 


“Senor Armando,” I started, “as you may know, I’m doing a great business selling cocaine in the city.” 


“Aha,” he said warily, “And?” 


“Well, I need to move a lot more money than this. A lot more.” 


“And?” he repeated. 


“I would like to use you exclusively to clean my money, but you’ve got to come down on your fee,” I said flatly.


“Okay,” he said after a minute’s silence. “Let me consider the fee.” 


“Alright, but don’t take forever. I can find someone else.” 


“I’ll let you know.” 


“I’ll let Carlos know you will be reaching out,” I said finally, noticing that the money was counted. 


I waited while he produced a check for $9,400. He handed it over and smiled. I smiled back. I knew I had him hooked. 


“You’ll hear from me,” he said. 


I walked out the door, into the lobby, then outside. I looked about warily as I crossed the street. I wouldn’t be safe until I was in my car. This time, I didn’t see any surveillance vehicles. Of course, they weren’t supposed to be noticed, I chuckled to myself. Most amazing of all, the dog never stirred. 


At the debrief, the team was thrilled with the meeting. Jen had already translated the substance of my conversation with Armando while I was inside the business. With the taped conversation, the case would be a slam dunk. I was thrilled to hear that no further meetings would be necessary. 


Within weeks, Armando was indicted and then arrested. His business was seized as well as all of his assets. I’m not sure what ever happened to the pitbull. I’m guessing it wasn’t seized by the government. 


Best of all, due to the strength of the case, Armando agreed to plead guilty and I never had to testify in court. 


The Undercover Coordinator, Michael McGowan, liked what he saw in me. A few weeks later, I was offered a coveted spot at the FBI undercover class at the FBI Academy. I would be headed back to Quantico.  


That is another story. 

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