Family Man: Doc Dolan and the author out for a walk in Chicago, 1952. In Doc’s left hand is a leash to one of his ever-present American pit bull terriers, likely Lady Girl. Chicago was familiar territory for Doc, and his daughter Mary was born there later that year. Courtesy of James Dolan

Crime

My Father, the Hitman

Doc Dolan was connected to the JFK assassination and some of Benny Binion’s bloodier work. When I was a kid, he pulled a con on me that I’m still struggling to understand.

My dad had gotten out of prison, and, for the first time in years, we were sitting down to dinner. It turned out to be the last time I ever saw him alive.

This was 1984. We were at Newport’s, in the West End, drinking Anchor Steam beers, and the mood was one of celebration. A former light heavyweight boxer, my dad was still physically imposing, even at 70 years old, but he was slimmer after his most recent stint inside. His sports coat hung loose on him, and his red-blond hair had thinned. It was a busy Friday night, and cheerful voices bounced off the brick walls of the restaurant. The air was perfumed with the scent of mesquite-grilled swordfish. We raised our glasses to toast my father’s freedom. I can still picture his big grin.

His name was James Dolan, same as mine, but everyone called him Doc. He’d been in and out of my life since I was a boy, but when I was in my early 30s, Doc and I reconnected. His life as a gangster, I’d learn later, brought him into the orbit of criminal organizations around the country, including Jack Ruby’s circle in Dallas. But long before I realized my father’s connection to the JFK assassination, I was just happy to have him back in my life.

I was a struggling 33-year-old psychotherapist trying to get a break in my field. He’d begun to open up a little about his own work, a process he’d begun with dozens of letters he’d written to me during his most recent time with the Federal Bureau of Prisons, first in USP Atlanta and then FCI El Reno, in Oklahoma. I’d always known he was a misanthrope, someone who didn’t have much regard for the law, but now he was getting specific. 

That night, we discussed his most recent bust for a three-card monte scam he pulled in Memphis before twice jumping bail. From there, he got to talking about the Dallas Campisi family, Italian restaurateurs who had a reputation for being in the Mafia. I’d gone to high school with members of the family. He described the Mafia narrative as an overblown fairy tale, something in his tone suggesting that he’d had experience with the real deal. He talked about Jack Ruby, how some said he was a Mafioso, too, how Ruby had “really wanted to be seen as a tough guy.” 

Being around Doc felt like being in a closed space with a circus tiger. It was exciting because there was a real danger, more than I realized for most of my life.

A few weeks before we met at Newport’s, he’d taken me to a bank and had me open a safe deposit box we could share. He showed me roughly $30,000 in cash, the most money I’d ever seen in one place. He said I could take from the box as needed, but he told me not to “hit it too hard.”

That night at Newport’s, he asked me about the house I’d recently bought in Oak Cliff. Unprompted, he said that if there ever came a time I couldn’t make the mortgage payment, I could “put it in the sky.”

I asked him what he meant.

“You know,” he said, gesturing upward. “Put it in the sky.”

I still didn’t understand.

“Like that little house in Miami,” he said. “I put it in the sky.”

I realized he was referring to the house fire that had prompted our family to move away from Miami in the early ’50s. I’d known about the fire but was too young when it happened to remember it. My mother sometimes made vague comments about my father having something to do with it, but now here he was, the man himself, talking about the house he’d torched.

I think I laughed, because I didn’t want to upset the mood, but I remember feeling baffled at the idea of so casually admitting insurance fraud, of setting ablaze the house he’d shared with a wife and two toddlers. Later, I’d learn that he’d done far worse. 

This conflict—between the titillation I got when my father brought me into his noir-ish underworld and the grief and sadness that accompanied that reality—has defined much of my life.

After we’d had a few drinks, my father left the waiter a $100 bill I’d seen him take from a stack in a briefcase in the trunk of his ’72 Buick Electra. We climbed back into the car, and he drove us through the deserted streets of downtown, telling me more about his time in the collections and enforcement business. He described dangling a man out the window of a room at the Adolphus Hotel until the man, as my father colorfully put it, “sang in nine languages.” Doc grinned and winked at me. Nervous, I grinned back.

San Antonio Express News front-page story
Sins of The Father: Six months after Doc Dolan’s murder in San Antonio, the Express News ran a front-page story connecting Doc to Jack Ruby and tying him to a conspiracy theory about the JFK assassination.
Courtesy of James Dolan

At one point, he advised me to stick with my career as a psychologist. He also told me how much he loved my mother, still, but felt she’d turned my brother and sister and me against him. The fact that he carried a torch for my mother after all those years of life on the road in motels, hooker cribs, hideouts, and prison cells brought a surge of sadness I feared would spill right there in the car. 

By the time he pulled up to my house, I was exhausted. I remember him driving away into the darkness. I remember worrying about his safety. I’m sure we talked on the phone a few times after that, but I don’t remember the content of the conversations.

A few weeks after Newport’s, I got a call informing me that Doc had been shot dead at his apartment in San Antonio. 

On December 4, 1984, I was alone in the house, having just taken my 4-year-old son to his daycare. I needed to gather up some things before leaving for work in North Dallas. The phone rang. I picked up. 

“Hello, Jimmy?” said a man’s voice.

The caller introduced himself as Sam and said he was a friend of my dad’s. He sounded friendly, like I knew him, but I didn’t. Sam was calling to tell me that Doc had been murdered at the door of his apartment that morning. Sam said there were no witnesses but that word was Doc had been killed by two associates with whom he’d been robbing drug dealers at gunpoint. It seems these two had figured it would be easier to rob a 70-year-old man than it would be to rob the young dealers. And, Sam said, Doc had about $50,000 in his apartment, but it was gone. He knew who the guys were, and he said he and his friends were “gonna get the motherfuckers.” He said I wouldn’t have to worry about Doc’s car, either. Sam said he would take care of it.

When he hung up, I rested my head on the kitchen table and cried like a lost child. 

The call kicked off what has become a 37-year search for truth and understanding. I wanted to know more about Doc’s life, all the parts I’d never been shown or couldn’t comprehend at the time. I wanted to understand this man, why he made the choices he had. And, of course, I wanted to know who’d killed him.

About a week later, I got a call from Richard Urbanek, a San Antonio PD homicide detective, requesting that I come down to go through Doc’s apartment with him. 

Urbanek was polite, respectful, professional. He wore street clothes and a cop mustache, his black hair trimmed neatly. He shook my hand before leading me out of the police station and into his cruiser to head to the Villa Fontana Apartments. A faint metallic scent of blood mixed with an undertone of rot hit my nose as we entered Doc’s efficiency pad. My father’s blood, I thought. My blood.

It struck me as more of a cell than a home. There was no art. A small table near a twin bed held a portable color TV. Against a wall, there was a wooden drying rack with t-shirts and underwear still hanging. Elsewhere, a stack of paperbacks, copies of The Ring magazine, an ashtray with a cigar stub. On his dresser sat a mix of matchbooks, paper scraps with nameless phone numbers, keys, eyeglasses. I was shocked to see syringes and ampules of scopolamine, a powerful hallucinogen sometimes used in kidnappings in Latin American countries. 

I spotted a small black-and-white photo with one corner missing. In the frame was a fat baby astride a pit bull terrier, with a young, dark-haired woman holding him steady. The baby was me, the woman my mother, and the dog may well have been Lady Girl. He had carried the photo with him for more than 30 years, through prisons, jails, motel rooms. A lump formed in my throat and wouldn’t let go. 

If you loved us so much, Doc, why did you leave? 

Urbanek asked if I had anything to say about what I saw in his apartment, anything that might not have belonged to him. When I said I didn’t, he said he had keys to what he thought were a couple of safe deposit boxes. 

The bank was expecting us. We crossed the polished floor with a manager jangling his keys. There was a moment of tension to see if Urbanek held the right keys, but soon enough there were two steel boxes on the counting table in front of us. Where or how the detective had gotten those keys was never explained. 

Urbanek lifted the lid on one box, then the other. The cash inside had been bundled into neat packets (like I’d seen in the box I’d opened with Doc earlier), with bills in every denomination from $1 up to $100. Urbanek had the money counted and it came to about $25,000. At the next bank, we had the same experience, finding about $20,000. 

“Hey, that’s your dad’s estate right there,” the detective told me. “It’s your inheritance.” 

In the mid-’50s, my mother took us to a place she called “the hospital” to see my father. I realized later it was the Seagoville federal correctional facility, in a small farm town southeast of Dallas. Doc was finishing a sentence begun at Leavenworth, in Kansas, and his transfer to Texas had triggered my family’s move to Dallas in 1954, when I was 3. 

Upon release, Doc held odd jobs, including carpet salesman at a Sears, but he eventually went to work for the American Guild of Variety Artists. AGVA (Agg-vuh, we called it) was an entertainers’ labor union, and Doc was the local head in Dallas. Those were heady times, and it seemed like our family was going in the right direction. Life was all about church and school—the catechism studies and the sacraments—but there was also occasional talk of strippers and visits to the AGVA office for what Doc called a “day at Daddy’s work.” 

There I found a big bulletin board covered with publicity photos of women dressed in scanty outfits, their breasts barely restrained. When we left for lunch, we ran into a little man in a plaid sports coat. My father said, “Jimmy, I wancha to meet Mr. Barney Weinstein,” and I recall his cool, soft little hand as we shook. Weinstein owned the Theater Lounge, where the infamous Candy Barr was discovered. Later I heard my father refer to Weinstein and his brother Abe as “the Heebs.” (I also remember my mother shushing him.)

Dog Days: Doc carried around this photo of his wife, son, and Lady Girl—taken outside of a Colorado cabin in 1951—for more than 30 years.
Courtesy of James Dolan

When I was about 9, Doc’s favorite dog, Lady Girl, had a litter in our garage. Doc had taken an interest in dogfighting and had bred her with that in mind, but he said I could have one of the pups, a sturdy brindle male I called Billy. Billy grew to become a powerful animal. I recall taking Billy to Kiest Park for training sessions that involved Billy harnessed to a rope that Doc held as he sat behind the wheel of our blue Ford coupe. Billy ran alongside the car, pulling us slowly, panting and foaming at the mouth with the effort. He never quit. 

At some point, Doc decided to take Billy on a car trip “just to see how he’ll do.” He returned without Billy and told me the dog had “gotten in a fight” and was hurt so badly that he had to be killed. 

In 1961, when I was 10, Doc’s mystery deepened. Some men accused him of using tear gas to rob their poker game of at least $26,000 in Beeville, Texas. I would have to go to Beeville to tell a grand jury that Doc could not have pulled the robbery because he had been at home telling bedtime stories about his boyhood adventures in Cedar Rapids, Iowa. I had no idea where he was on the night of the robbery, but I was more than ready to tell anyone that my dad was a good man. I felt grown up but still frightened, thinking that it was up to me to keep my father from going to jail. 

His lawyer, Sissy Farenthold, was a colorful, well-known attorney in Texas. I recall sitting on a patio behind her house in Corpus Christi, the humid air ripe with the scent of rotting oranges. I couldn’t stop fidgeting. 

At some point, Doc decided to take Billy on a car trip “just to see how he’ll do.” He returned without Billy and told me the dog had “gotten in a fight” and was hurt so badly that he had to be killed. 

Eventually, we drove to Beeville and to the courthouse, where Doc was no-billed and my testimony was not needed. I was overjoyed and then a little upset that we’d come all that way only to not tell the court my story. I couldn’t help but think about the shotgun and shells that I’d seen hidden in his closet. 

One night a couple of years later, my brother, sister, and I were lying in our beds under woolen blankets, listening to the Beatles on our transistor radios, when my mom stepped into our room and told us there were some men looking for my father. FBI, police, I don’t remember. I only recall my terror. 

“Just stay in bed,” she said. “They’ll be gone soon.” 

I lay still with my heart thumping away in my chest, listening to the men talking to each other, calmly going about their business. The search seemed to go on and on. Then they were gone. 

What did he do now? I thought. I buried my face in my pillow and let the tears come, choking down sobs. I wanted to save him but didn’t know how. 

Sadness and shame hung over my home. I felt guilt over my powerlessness. To shore myself up, I unconsciously modeled my father’s behavior. A streak of dishonesty emerged as I grew into an adult. A few examples: I forged documents in a loan application. As a young married man, I was unfaithful more than once. For a period in the early ’70s, I attempted to become a pot dealer. I once got fired from a job at a printing company for composing an obscene headline to an article in a church newspaper. 

There’s a cliché among research psychologists that those who become therapists are really trying to help themselves, and the cliché is entirely true.

In May 1985, a lawyer called to tell me probate was complete on Doc’s estate, which amounted to a brown paper bag holding $45,000 in cash, a Seiko watch, a cheap ring, and some odds and ends. The lawyer asked if I had seen the San Antonio newspaper. “They did a big article on your dad’s murder,” he said.

The front page of the Express-News from May 19, 1985, bore the headline “Man Slain in S.A. Tied to JFK Assassination.” Near the headline was a picture of Doc wearing tinted glasses. On the inner pages were photos of Carlos Marcello, Felix Alderisio, and Santo Trafficante. Marcello and Trafficante were thought by some in law enforcement to have ordered the hit on JFK. My heart thudded in my ears as I read the story. For the first time, I felt like I could see behind the curtain that my father used to hide his life.

Doc Dolan on the streets on New Orleans
Doc on the streets of New Orleans, where he lived while he was a merchant mariner.
Courtesy of James Dolan

A few years earlier, Doc had ended a phone call by saying to me, “I don’t know anything about who whacked Jack Kennedy.” At the time, I was confused. But the Express-News story connected Doc to Jack Ruby and tied him to a JFK conspiracy theory. The reporter, Bill Hendricks, wrote that Doc had done collections work for these top Mafiosos. I learned that in his youth he’d worked for a year in a California hotel and served as a structural iron worker before joining the Army. 

In the late ’40s, Alderisio had sponsored him in Chicago. Doc was also associated with the Smaldones of Denver (my birth town) in various swindles. He had been arrested, convicted, and put on probation for impersonating an IRS agent and sent to Leavenworth, then to Seagoville, after violating his probation. The FBI at some point labeled him “one of the two most notorious hoodlums residing in Dallas”—even though his neighbors at Villa Fontana were quoted in the Express-News article saying they thought of him as friendly and “such a nice man.”

 When he was killed, according to the newspaper article, Doc was a key witness in a probe of South Texas drug dealing and contract murder. The investigation was code named Operation Bushmaster, and just hours before he was killed, he’d negotiated through his attorneys for immunity from federal prosecution in exchange for his testimony before a grand jury. According to the story, “Six 9 mm bullets pumped into Dolan late last year put the grand jury out of business.” That jolted me. It seemed logical that his murder had been a hit. In fact, a detective was quoted in the story saying, “…it doesn’t appear the motive was burglary or robbery.” 

I thought back to my conversation with the man calling himself Sam. Why did he tell me it was a robbery? Was Sam in on it? Had I actually spoken to the man who had murdered my father?

Doc, I finally understood, was a hardcore criminal who had practiced his trade with ferocity. In my naive denial, I had wanted to see him as a hapless ne’er-do-well, a nonconformist with a streak of dishonesty. I liked to think of him as a latter-day Robin Hood. Now I knew that wasn’t true.

I called Hendricks, the reporter. He said he was sorry that he’d forced me to confront the truth. That hurt so much that I got pissed off and hung up on him. Anguish upon anguish. 

The ordeal, though, raised a new question, something that had never occurred to me when I was younger but wouldn’t leave my mind now. I wondered if my father had killed anyone. 

In the late ’90s, a woman responded to a query I’d posted on a JFK bulletin board. She said her name was Laura, that she was a single mother of three, and that she had spent time with my dad in San Antonio while he was on the lam in the mid-’70s. They’d corresponded when he went to Atlanta and then to El Reno. She said he was “one of the kindest, gentlest men” she’d ever known, which made me skeptical, but she offered to send me the letters he’d written. I readily accepted. 

In the letters, Doc mentioned me and my brother and sister very little. He told Laura how much he cared for her, and he claimed to have visited her through astral projection. Even now, this glimpse into a corner of Doc’s mind I never knew about is just incredible. 

I never heard from Laura again. But I have many times wondered about the life my father lived beyond my knowledge. Who was he with? And where? And for how long? And what about the woman with three young children in Dallas he left behind?

Reading Doc’s letters to Laura, I was saddened to see his longing and wondered if perhaps my mother, my siblings, and I had been only incidental players in his drama, a few of many, with him presenting a different version of himself to each. 

Evidence of that began to grow.

One night in the early 2000s, I was getting onto the Dallas North Tollway on the way home from a busy evening schedule at my office. My phone rang. The caller was a youngish-sounding Hispanic man I’ll call Jesse. He told me he’d grown up with his dad’s close friend Uncle Jaime often sleeping over in the spare bed in his room. He eventually learned that Uncle Jaime was Doc Dolan, not a real tio, as he was a big blanco with reddish blond hair. 

As Jesse grew older, he learned that Doc and his dad were partners in armed robbery in and around Houston. He said they got his older brother involved, and they tried to get him into the trade as well, but Mama wouldn’t allow it. His older brother was arrested several times and eventually had to do hard time. 

His dad and Doc were so close that when Doc got out of prison, his first stop was a visit to his former partner’s home in Houston. Jesse said his father got Doc a hotel room and a couple of hookers, and the next day, “them old gals said that Doc wore them both out—at his age!”

Portrait of The Con Artist as a Young Man: Doc (bottom row, second from left) on his high school basketball team in Cedar Rapids, Iowa.
Courtesy of James Dolan

Jesse told me it was great to speak to me and share his memories. He thought my father was a wonderful guy, and he admired him a great deal. As I was in the car at the time, I was unable to write anything down, so I asked him to email me everything he could remember about Doc and his father. But I never heard from him again. 

Jesse’s story left a leaden feeling in the pit of my stomach. Every time I learned something new, it seemed to kick me all over again.

Late in 2019, I finally received Doc’s heavily redacted FBI file. It is 1,500 pages covering only the years 1971 through 1978, when he was on the lam after pulling a swindle in Memphis. The file contained page after page of mundane reportage on his movements and associates. I read it all, searching for some final truth about him, worried that each page I turned would bring a detail I didn’t want to know. 

I’d already been warned. Doug Swanson is a former Dallas Morning News reporter and author of Blood Aces, a superb book on the famous hoodlum Benny Binion, who ran gambling parlors in Dallas in the ’30s. Swanson had called me earlier, trying to verify information he had uncovered related to Doc and the 1972 Las Vegas car-bombing death of attorney William Coulthard. Binion had wanted Coulthard taken out. The likely bomber? Doc Dolan. 

Working through Doc’s FBI files, I eventually found something that stopped me cold. I came across a narrative of Doc attending a cockfight in the Trinity River bottoms near Northwest Highway in 1973. An informant placed him there and implicated him in the murder of two men who were also there and had stolen a moneymaking dog from an associate of Doc’s a week prior. Their bodies were found on New Year’s Eve at a campground on the Elm Fork of the Trinity, with gunshot wounds to their heads and their hands bound behind them with neckties. 

Somehow the Coulthard bombing seemed abstract, while this cockfight scenario seemed too real to me and churned my stomach. Doc was a murderer. 

Earlier this year, I answered a call while driving. A woman with a deep country accent was on the other end. She reminded me that her daddy and Doc had once been the closest of friends. I remembered her daddy’s name from childhood. She was drunk and rambling. She described herself and her family as Mafia. I was wondering what the nature of the call was when she blurted out, “I think my daddy kilt your daddy, cuz I think he was afraid with that big investigation that Doc would testify on what all we was up to.” I assumed she was talking about Operation Bushmaster.

I tried to get her to tell me more, and she said her father and mine were in a widespread crime ring together, and that they knew each other from dogfighting circles. The more she talked, the more plausible it all sounded. 

I now have at least three plausible scenarios for Doc’s killing: 

  1. The original theory of robbery by criminal associates. 
  2. Revenge by the victims of the robberies he’d committed with those same associates.
  3. A hit to prevent his testimony in the Operation Bushmaster trial, executed either by the caller’s father or by some other person with the same motive. 

In the weeks since typing the previous lines, the various strands of theory regarding who killed my father have led me to an obvious conclusion that can never be proven. I believe Doc was killed by a small group of individuals who’d known him for some time and who knew he was trying to get out of the game. He was known to have wanted to relocate to Arizona to be in the vicinity of my mother. He was a federal witness in an organized crime probe. He was known to have a large amount of cash in his apartment. All of this made him a liability.

Doc Dolan as a light heavyweight boxer in the Army
As a light heavyweight boxer in the Army.
Courtesy of James Dolan

I add that the San Antonio police hardly conducted an investigation into Doc’s death. I should have requested those records decades ago. After my day with Detective Urbanek going through safe deposit boxes, I never heard from the cops again, until I contacted Urbanek in the late ’90s. He more or less corroborated Sam’s story of the unseen criminal associate assailants. But how did the murder of a key federal witness not lead to a larger investigation? Or was it investigated and I was never informed?

This small group—Sam the unknown caller, the woman who thought her daddy did it, the criminal associates in drug dealer robberies—came to the same conclusion, based on their varying motives: it was Doc’s time to go. This is my current working theory, and I’m sticking to it. I’ve given up the idea that I will ever know what really happened. But this makes the most sense. 

At least for now.

One night after a few beers, Doc told me a story about a machine he once sold to suckers. This machine, with the turn of a crank, would print perfect $100 bills. Thing was, it didn’t really print them. The machine spit out bills that had been loaded into it before its demonstration, just enough to convince the buyer. He told me the marks paid big bucks for a counterfeit counterfeiting machine. 

Did the machine actually exist? I don’t know. But his pantomime of how it worked was believable, and, what’s more, I wanted to believe it—in the same way I wanted to believe when I was a kid that Davy Crockett killed a bear with his bare hands. 

If he actually sold the machine, even once, that feat of grift put him in the pantheon. Telling the story, his eyes sparkled with mirth while I filled with pride and laughed along with him. 

But beneath the laughter and the shame-shaded pride, I was sad. No, it was something else: pity. This brilliant, witty, handsome, charismatic man had accomplished nothing. He left his wife to raise his children on her own while he roamed the country committing murders, arson, armed robbery, and who knows what else. 

I’ve been asked more than a few times if I’ve ever visited his grave in Mission Park cemetery in San Antonio. Yes, I’ve been there once, at his funeral service, such as it was.  His attorney, Alan Brown, stood at a distance with the door to his Jaguar open and the motor running while a mysterious guy no one knew stepped up and sang “Amazing Grace.” I’ve not been there since.

Perhaps the counterfeit counterfeiting machine was his greatest achievement, even if it never existed. Simply conceiving of it showed the workings of his mind. Life itself is a long con: find your mark and give it what you got.

I’ve wandered for years in the mirror palace of my father’s life, always driven by the idea that I’d eventually arrive at the final truth, and here it was sitting in plain sight: everyone in his life was a mark, with something in his or her heart that made him or her vulnerable to his con. Maybe it wasn’t larceny or greed. Maybe it was the desire to love and be loved. And maybe the only way he could show love was through a con. 

I realize now that he groomed me from childhood. I was his perfect mark—and still am. I’ve found ancient yellow pads in my student papers from 50 years ago bearing the first paragraphs of my attempts to write this story. I see in them the beginnings of how I chose my profession, and sometimes I fear that I, too, am a confidence man, selling the proposition that hours of conversation with me will change a life. 

I might be the only buyer there ever was for the counterfeit counterfeiting machine, its first and best customer. I openly admit I bought the con, and I knew it was the only way to be close to Doc. For all the trouble it has caused me, all the PTSD, the night terrors in childhood, the harassment by the FBI—all of it—I have no regrets.  

Because I am still his mark. As I type these lines, I am still searching to understand him. And the search will go on. 

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