Jimmy DeVito: My Worst Best Friend

[Disclaimer: The name Jimmy DeVito was chosen arbitrarily. I know no person named Jimmy DeVito, and any similarities to anyone named Jimmy DeVito are purely coincidental. The story about Jimmy DeVito is a work of non-fiction, except for the name.]

You ever meet a guy you believed in so much that you were willing to overlook all of his glaring flaws? The theme of this article is disappointment. The original theme of this article was naïveté, your naïveté, and naïveté in general. I loved Jimmy DeVito like a brother, but looking at the laundry list of things this guy did to me, it’s hard to believe that I fell for so much. I also included a love letter to my dad for helping me not fall for every DeVito plan, because I didn’t fall for everything, and he’s one of the primary reasons I didn’t. I didn’t follow Jimmy DeVito to financial ruin, but I maintained an irrational level of loyalty to a kid, a young man, and a man who tried his damndest to pull me down.    

“If he would’ve just said no in the beginning, his life wouldn’t be in ruin,” is something we’ve all said about someone at least once in life. I empathize with those people, because I know, firsthand, how hard it can be to say no. Watching a toddler learn the language, we learn the power of no. “Do you want to play with this toy Tommy?” “No,” they say. They look around the room. They see the power. “Tommy? C’mon, these people were kind enough to let you play with this toy.” “No!” they say with more power in their voice. They know the power. They feel it. As we grow older, we realize that no hurts feelings, and it damages relationships. No matter how morally ambiguous the situation is, it’s always and nicer easier to say yes. Yes makes everyone happy, it’s a display of loyalty and trust, and it bonds people for better or worse. Yes is also simple, and when we come to that fork in the road we prefer simple. It can feel so harmless and insignificant to say yes, because it’s a one-and-done.

When you stand at that proverbial yes/no fork in the road, my advice is protect yourself. Protect yourself as if no one else will. I was lucky, I had an old-stick-in-the-mud dad, who didn’t believe in anyone. He thought most people were pieces of junk who were up to something he couldn’t even see. He was as cynical as a man could be, but at that time in my life I needed that. I was so eager to believe in people that I now realize I used them to foster belief in myself. My dad offered me objectivity, the yin to my yang, and the negativity to my positivism. My dad advised me to protect myself so often that I became a little too over-protective of myself. I would’ve detested you for saying this in my teens and twenties, but if it wasn’t for my dad I wouldn’t be in the position I’m in today, writing this to you. 

It’s almost as easy to make the second decision as it is the first one, because nothing happens after the first decision. So little happens after that first decision that we fall prey to the conceit that we were right, and those who warned us to protect ourselves were wrong. They thought it would be so foreboding and damaging, “It’s not,” we say. “It’s easy.” Something happens along the way, though. By about the third decision, you can hear the links snap into place on the chain, as you feel apart of the machine, and you can no longer say no. At some point in between it dawns on you that you’re in too deep to say no now. This is the part of the movie where our cringe goes so deep that we want to turn it off, because we know the main character of the movie should’ve said no in the beginning. If he just said no, none of this would’ve happened to him, but we can’t shut the show off, because we can’t help enjoying the other person’s pain, and we can’t look away. 

I saw these movies so many times that when Jimmy DeVito asked me to open a bar with him, I considered it one of those cringeworthy, first decisions. I looked into the future, and I saw how all of this would play out (thanks Dad!). I knew Jimmy’s father owned a bar, and that that bar engaged in some illegal activities. Would Jimmy lead me down a similar road? What happens soon after the bar begins to fail? How do we save ourselves? Are we so desperate for a cash infusion that we give his parents a  percentage of ownership? What happens then?

No matter what happened, I knew I would be the silent partner prone to invisibility, under Jimmy DeVito’s wing, because Jimmy was so charismatic, funny, and impulsive, and if I opened this bar with Jimmy, I would be subjected to his impulsive whims and desires? Maybe not in the beginning. In the beginning, Jimmy maintained a rational face, but he loses that over time, and he beats you down with it. I also recognized that I would probably be financing a sink hole, until I went broke, and the venture culminated in a “Sorry buddy!” followed by a “We probably shouldn’t have done it in the first place. What were we thinking? We were twenty-years-old.” 

Jimmy is very persuasive when he wants it, but once you do it, and the ramifications come thundering down on your head, Jimmy basically calls you an idiot for ever listening to him in the first place. “Why would you listen to me on anything?” was a question he asked so often that it rang in your head every time he came up with an idea. In the planning stages, Jimmy was a big, old “we” guy, but when things begin to fall apart, it’s “What were you thinking?” Prior to this impulsive idea to buy a bar, a largely beer-induced idea, Jimmy’s ideas were small and the ramifications minimal, and I fell for all of them. Jimmy’s out was, ‘C’mon, we both know who I am. You should’ve known better.’ This allowed him to avoid feeling any guilt for putting me in a precarious situation. I was not a sensible person, but between the two of us, I was the sensible one.  

This impulsive idea to buy a bar was a beer-induced conversation spread out over the course of months, until it got real. “I’m sick of all this beer talk,” he said. “We need to get real here.” He told me that his parents would help us attain all the licenses we needed, they could scout the proper location for us, and (cue the deep, dark piano keys) they could even help us secure a loan. For all I knew, the bar idea was his parents idea.

“If we’re getting real here,” I said. “Then I gotta say no.” 

I was not only “so tight with my money that you could hear the squeaks when I walked” with Jimmy, the whole DeVito family joined in. “When you open your wallet, moths fly out!” the matriarch of the DeVito family said. It was all funny and fun-loving, but they knew my weaknesses, they knew how much I abhorred selfishness and narcissism, and they knew how to prod. It was always four-on-one with them, and their constant teasing, but I didn’t relent. Not on the big stuff. 


When Jimmy’s wife got into a car accident that was her fault, and it resulted in litigation, Jimmy asked me if I could be a star witness to this accident. I was not in the car, or on the scene, but Jimmy told me that they would work on a testimony that would appear faultless. “You could sign a written affidavit,” he said. “You likely would never have to appear in court.” 

“What if I do?” I asked. “What if I mess up? What if their lawyers trick me into exposing the fact that I was not there?”

“The lawyer will work it out so that never happens. You know what they do with their legal chicanery.”

“So, you’re asking me to lie under oath?” I asked.

“Witnesses mess up crucial details all the time,” he said. “Don’t you watch Law & Order?”

“You’re asking me to commit perjury?”

“It might never come to that,” Jimmy said. “There’s still some doubt that she will go through with this suit. The lawyer thinks the woman is seeking a settlement, but if she does, I want to know if I can count on you.”

“I can’t do that Jimmy.” It pained me to say that. I was a little miffed that Jimmy would put me in the situation of having to say no, but more than that I didn’t want to disappoint the man. It didn’t matter what it was, Jimmy didn’t take rejection well. If you told Jimmy that he couldn’t have a bite of your tuna sandwich, because you felt weird about giving people bites of a sandwich, he held it against you for weeks. Jimmy led you to believe that any rejection, of any kind, could bring about the end of your friendship and maintaining the friendship was always my chief concern. To anyone who can’t understand why a friendship might be so precious, I ask them if they’ve ever been on the nerd end of our friendship clinging by their fingertips. 

“All right,” Jimmy said after I managed to ‘no’ my way through all of Jimmy’s promises and provisions. “I’ll get someone else to do it.” This was Jimmy’s way of pounding one nail into the coffin of our friendship. It was his way of saying I’ll just turn to the next fella in line, and he said it with a pregnant pause that awaited the, “Wait Jimmy!” Jimmy knew how much our friendship meant to me. We both knew it meant ten times more to me than him, and he dangled it. My no answer was a lack of loyalty, no matter how I spun it. It was a rejection that came with ramifications. 

Jimmy pitched his ideas to me with an elevator-style pitch that authors use to try to generate interest from publishers, knowing that they only have six proverbial floors before that elevator hits the ground floor and the publisher exits. He hinted at the affect my refusal might have on our friendship, and he hinted how I might redefine my courage in his eyes. This is when we want to stop the movie, but we never do, because we can’t help but enjoy watching a person unravel. The one exception to my story was I almost always said no.

Jimmy DeVito wasn’t just a friend of mine, he was my best friend, my brother from another mother and father, and a person I believed in. Jimmy DeVito tried to steal my girlfriend one weekend, and he claimed he was never attracted to her. So, why did you do it? “Because I wanted you to see what kind of girl you were with?” (For the record, she said the same thing in reverse.) I accepted Jimmy’s apology, not her’s, because I he was my best friend. He had relations with another woman I was seeing, but I didn’t see her long enough to develop feelings for her. He forged my signature on a check, to buy some pizza, and he wrote, “Sorry buddy!” in the notes section. I pretended I never saw it. 

“You need to learn that you cannot trust anyone in life,” Jimmy told me, as if in reaction to all he did to me, “outside of your immediate family. And even then… even then, you should be so skeptical that you trust and verify.”

When Jimmy would go out to cheat on his wife, he told her he was hanging out with me. When his kid begged and pleaded with him to spend more quality time with him, he told the kid he was hanging out with me. He wasn’t hanging out with me on almost all of these occasions. Yet, his son dislikes me to this day for taking his dad away from him during those crucial years. The funny thing was when I would call him up to see if he wanted to hang out, he told me that he needed to spend some quality time with the wife and child. 

When he fell in love with another woman, and she rejected his plan to move their relationship further, a dejected, empty Jimmy DeVito turned to me for counsel.

I stayed up into the wee hours of the morning listening to this man pour his heart out. I advised him the best I could, but it was a very difficult position for me to be in, because I knew his wife, and I liked his wife. I thought continuing in the marriage he’d been in for twenty years was the best course for him, but I knew that he was so in love with this other woman that rationality would not matter.

“If you’re not happy with her, divorce her,” I said. I then said something like, “but be careful, the grass is always greener, and all that.” 

When that relationship ended, and he stayed with his wife, he told me that I never checked up on him to see how he was doing. I was shocked too, because it was true. I didn’t call him, or email him to see how he was doing. That wasn’t like me, and I was confused, until I remembered that my dad died the same morning of his late night/early morning confessional. I told him that my dad’s death distracted me. 

As with most normal, teenage boys, I had a mess of friends here and there. I had work friends, sports friends, video game friends, and neighborhood friends, but Jimmy was one of the first and last comprehensive, best friend I ever had. I knew that friendships were conditional. I knew I had to be funny, entertaining, and insightful in a fun and entertaining way, or my best friend would find someone who was more of all that. I also knew that I should hold him to various conditions, including loyalty, honesty, and some measure of compromise on his part. My idealistic images of our friendship kept getting in the way of rational thought.

“I don’t know how you could be friends with him,” more than twenty people have said to me. They point out Jimmy’s flaws, his lack of loyalty, his complete lack of any integrity, and all of his other glaring flaws. 

My response has always been something along the lines of, “He’s a friend. We’re not married, and we have no contractual or legal bindings. I know what he’s done to me, and I know what he’s done to others, but how often in life do we have best friends? How much do we overlook with the hope that they will be friends with us for one more day?”

I know numerous adults who’ve never had an adult, best friend. Most adults hang with the family, and they spend most of their free time around work associates with whom they bond over the course of a work week. They grow to like them so much that they’re like family, but they’re not best friends. We all had best friends in the neighborhood when we were kids. We can probably still list off our top five best friends in grade school and high school, but after graduation everyone broke all those promises to be friends forever and moved out or moved on into adulthood. We might do lunch with them a couple times over twenty years, and we might meet for informal or formal reunions, but most of our adult lives are spent around our family, our extended family, and work associates. 

Jimmy DeVito wasn’t just fun to be around, and he wasn’t just a funny guy. He had room-drawing charisma. He gave you something to believe in. A night out with friends is fun, but when Jimmy decides to hang out with you, it results in a night everyone remembers for weeks. He was/is just one of those type of guys. He was that one percent of the people you look forward to sitting with and eating a sandwich. There was something about Jimmy DeVito that you always wanted to be around. He didn’t have a level of charisma to which we ascribe cult leaders, but after spending time with Jimmy, you might get some insight into the cult of personality. It wasn’t the big things with Jimmy, just as I’m sure it’s not with cult leaders. Jimmy made all those tiny, almost imperceptible connections, and those connections were true. He didn’t make those connections he made to perpetuate fraud. He genuinely liked you, as I’m sure he regarded me as a brother just as much as regarded him as one. He was just one of the most impulsive individuals I’ve ever met. His impulsive desire to have fun overrode his good sense and his sense of loyalty and morality. I don’t keep records on such things, but I think Jimmy DeVito might’ve disappointed me more than anyone else in life.  

It feels odd to write that Jimmy disappointed me, because I’m not his parent, his wife, his child, or anyone who counted on him in any substantial way. So, why does my disappointment in him matter? It doesn’t, except that I believed in him. I didn’t believe he would go onto bigger and better things, or that was never a primary concern of mine. If he was successful, I would’ve applauded him, and if he wasn’t, I would’ve felt sorry for him. I didn’t care about any of that. I just wanted him to be a friend.

It’s important to note that no matter what Jimmy DeVito did, he really wasn’t a bad guy, or an awful person, he just wasn’t what we wanted him to be. He wasn’t the husband his wife thought he should be, the dad his kid thought he could be, or the friend I thought he would be, but we all stuck by him. Jimmy’s answer, or the answer he gave me on an unrelated matter, was that he was just too impulsive.

“You know me,” he said in an uncharacteristically vulnerable moment, “I have no control. You put a product in front of me, I’m going to buy it, regardless if I have the money. You put a drug or an eager woman in front of me, and I’m going to indulge. I’m not going to calculate the ramifications. I’m just going to do it. I have no control of my impulses.”

When they finally lay Jimmy DeVito in the ground, the gravestone should read, “Here lies the Jimmer!” The Jimmer was Jimmy’s alter-ego, a name he gave himself instead of say, “Jimmy fun time!” The Jimmer was the side of Jimmy that would forsake and betray those who loved him most for the promise of a good time. The Jimmer wasn’t loyal to anyone but himself and the promise of whatever form of gratification another could offer him. The problem will arrive when they do lay Jimmy and the Jimmer in the ground. If it rains, the only people who show up will be those Jimmy taught a vital lesson in life, even the people we love most in life can disappoint us.