Road to Perdition

by Max Allan Collins

  The boy was nodding. “Backup plans.”

  “That’s a good way to put it.” He patted the boy’s shoulder. “You’ll be fine.”

  On his way toward the exit, O’Sullivan noted his reflection in a mirrored wall—he looked pretty rough; unshaven. He ducked into a bathroom and threw water on his face, ran his hands through his hair, doing his best to spruce up.

  With his father gone, Michael got into his little suitcase; there, among some clothes, were his pipe, his dice, and two Big Little Books, a Tom Mix and the Lone Ranger one that he was still reading. Selecting that one, the boy sat and thumbed it open. His eyes looked at the full-page picture at right, of the Lone Ranger holding a gun on a sheriff. The caption, redundantly, said: “The Lone Ranger had the Sheriff covered.”

  Five minutes later, in the vast room, surrounded by big-city strangers, the boy was still staring at the same page.

  Then, his face blank, he shut the book, pushed it aside; he felt his lower lip begin to quiver and his eyes began to get wet, his whole face quivering, as if he had no control over it, which he didn’t.

  The boy put his head on the table, the way the nuns at the Villa had the students rest at their desks, and he wept, trying to stay quiet, and not attract attention, because his father wouldn’t have liked that.

  At 22nd Street and South Michigan Avenue, the Lexington had once been one of Chicago’s most elite hotels, and the ten-floor structure still made an impressive appearance, with its turreted corners and bay windows. O’Sullivan had been here before—also at the former mob headquarters, the Metropole Hotel, just a block away. The Capone organization had the run of the place, controlling the third, fourth, and tenth floors and scattered rooms throughout, many of the latter taken up by the numerous hookers and showgirls Capone kept salted away for the convenience of himself and his boys.

  Standing across the street, eyes on the marble pillars framing the entrance, O’Sullivan knew full well he was entering a mob stronghold. Capone had put in alarms, moving walls, hidden panels, and Christ knew how many other security measures. Though the hotel looked normal enough—doormen and bellboys thronged the glass doorways—the lobby would be crawling with Outfit gunmen. Nonetheless, as an expression of good faith, he was unarmed, the .45 and his other weapons left behind in the parked Ford. All O’Sullivan had on his side was the unexpected boldness of what he was about to do—that, and his reputation.

  Moments later, O’Sullivan was walking across the magnificent lobby, across the black-and-white checkered tile floor, toward the iron-grille elevators. One of those elevators—which no one seemed to be using—stood vacant, while on either side of it, two watchdogs in Maxwell Street suits stood guard.

  The brawnier of the two leaned against a wall, reading The Racing News. The other one—taller, skinnier—was smoking a cigarette, rocking on his feet, eyeing the floozies who were a part of the odd Lexington mix that included a surprising share of legitimate guests—salesmen and other professional types, in Chicago on business.

  O’Sullivan approached, saying to the brawny watchdog, “How are you, Harry?”

  Harry looked up from his racing paper, obviously startled to see this unshaven figure. “Mike!…Mike O’Sullivan. Yeah, uh… hello.”

  O’Sullivan looked at the taller watchdog. “Marco, isn’t it?”

  Marco nodded, warily.

  Harry said, “Hey, uh, Mike—heard about what happened. Christ, it’s awful. How you holdin’ up, pal?”

  O’Sullivan said, “I need to talk to Mr. Capone.”

  Marco, who didn’t seem to know what Harry was talking about, said, “Mr. Capone is out of town.”

  “Mr. Nitti, then.”

  Marco shrugged. “You ain’t on my list.”

  O’Sullivan smiled. “Like to be on mine?”

  The watchdog paled. “I don’t mean any offense, Mr. O’Sullivan. I just got a job to do.”

  Harry said, “Mike, Mr. Nitti’s awful busy today.”

  “I’ll wait.”

  The two watchdogs exchanged glances; both of them knew only too well who and what Mike O’Sullivan was.

  Harry shrugged. “Okay—Marc, take the man to the top.”

  Marco stepped inside the elevator and so did O’Sullivan.

  “Meaning no disrespect, Mr. O’Sullivan,” Marco said, “you’re gonna have to stand for a frisk.”

  “Fine. But I’m not packing.”

  Marco patted O’Sullivan down, found nothing, and said, “Friendly visit.”

  “Always.”

  Marco swung shut the grille-work doors. Ten floors took a while, and they rode in silence at first, then the watchdog asked, “How’d you remember my name? You only saw me, once. We never even spoke.”

  “I make it point to remember men’s names.”

  “Yeah?”

  “Men with guns.”

  Marco thought about that, then asked, “What was Harry talkin’ about? What’d he mean, how are you holding up, you don’t mind my asking?”

  “I do mind,” O’Sullivan said.

  The elevator continued on its slightly jostling course, making no stops along the way.

  “Quite a reputation you got,” Marco said, perhaps starting to resent O’Sullivan’s understated lack of respect.

  “I don’t know how that happened,” O’Sullivan said.

  “How do you mean?”

  “I don’t remember leaving anybody to spread the word.”

  And then they were there, at the top floor waiting room, where politicians and businessmen of varying degrees of respectability mingled with shadier-looking figures. Cigarette smoke floated like a blue haze as the men sat and chatted, talking business and sports and even family, drinking the coffee provided thoughtfully by the Capone organization.

  Everyone was settled in for a wait, and O’Sullivan had left his son with that hour-and-a-half deadline. He gave the receptionist—a pleasant if officious thirtyish woman who sat near the focal-point door marked PRIVATE—his name, acknowledged he had no appointment, but suggested she tell Mr. Nitti that Mr. O’Sullivan was here. Then he took a seat.

  After a while, when she had not yet done as he’d asked, he settled his gaze on her and, when her eyes met his, he checked his watch and raised an eyebrow.

  The receptionist got the message—though she did not recognize O’Sullivan, she clearly could see that he was not a part of the political/business crowd taking up the other chairs. And, despite the pretense of normal business the Capone organization made, even a receptionist like this knew the score: the deadly-looking unshaven man should not be kept waiting.

  She spoke to her boss on the intercom, then looked up at O’Sullivan and nodded.

  He thanked her, as she held open the door for him.

  The office was spacious, a lavishly appointed executive suite worthy of LaSalle Street, all dark woodwork, with a desk and a conference table, and of course a fireplace, over which hung an oil portrait of Al Capone.

  Frank Nitti did not cut the imposing figure Capone did, either in the portrait or in life. A small mustached man in his midforties, Nitti was in his white shirtsleeves with dark suspenders, but his gray and black tie was not loosened, and there was nothing casual about the well-groomed former barber. As he approached his visitor—offering a hand, which O’Sullivan shook—Nitti seemed typically cordial yet distant.

  “I didn’t know you were waiting out there, Mike,” Nitti said. He was smoking, a cigarette in his left, gesturing hand. “But I have to admit I’m not surprised to hear from you…Come, sit.”

  “No thank you. I can’t stay long.”

  Nitti shook his head. “I’m pleased that you would think of us, in your time of grief…We all just heard. You want some coffee?”

  O’Sullivan shook his head. “Thank you for seeing me, Mr. Nitti.”

  “Don’t be silly. Al is in Florida, holed up with his lawyers. Some legal matters pending, and I haven’t talked to him about your situation yet. But I know he’ll be distressed b
y this loss. He’s a family man, too…”

  “I know. Thank you.”

  “And allow me to offer my personal condolences on your tragic loss.” Nitti gestured. “Come! Please…sit…”

  They sat facing each other across a small table, next to a window that offered a commanding view of the South Side of Chicago—the Capone/Nitti empire.

  Sympathies expressed, Nitti’s manner shifted to businesslike. “Now—what’s on your mind, Mike?”

  “You heard about my family. But what did you hear about Tony Calvino?”

  Nitti lighted up a new cigarette. “That you killed him.”

  “Self-defense.” O’Sullivan dug in his suitcoat pocket. “John Looney’s son Connor sent me to Calvino’s to deliver this sealed message…”

  O’Sullivan handed Nitti the note; the bantam gangster read the words—KILL O’SULLIVAN AND ALL SINS ARE FORGIVEN—and said, “Jesus—the man sent you there to die. To be killed.”

  “And then Connor went to my house, my home, to kill my family. You seem to know that he murdered my wife and one of my sons.”

  “Yes. Yes…”

  “Last night, before I shot him, Frank Kelly told me that Looney is protecting his son. He’s hidden him away.”

  Seemingly unimpressed by the reference to the Kelly murder, Nitti shook his head, disgusted. “And you served Looney’s interests well, and honorably, for years! There’s no excuse for such vicious behavior. We’re not animals—we’re businessmen.”

  “Yes. And I have also served the Capone interests ‘well and honorably,’ over the years.”

  Nodding in a that’s-old-news manner, Nitti said, “Through our alliance with the Looney family…Why did you come here, Mike?”

  “I don’t seem to be working for the Looneys anymore.”

  “That’s a fair assessment.”

  O’Sullivan paused; rather formally, he said, “I would like to work for you, Mr. Nitti. For you and Mr. Capone.”

  That seemed to catch Nitti off guard; he exhaled smoke, then said, “Well now, that’s a very interesting notion, Mike. You are the best at what you do.”

  “Thank you. But for me to join your ranks, and be your loyal soldier, I need you to turn a blind eye to what I have to do in the coming days.”

  “And what’s that?”

  “Kill the man who murdered my family.”

  Nitti blew out more smoke. “Connor Looney…And what about his father?”

  “I have no desire to kill the old man. I would prefer he suffer the hell on earth of losing a son.”

  For endless seconds, Nitti said nothing, sitting still as stone.

  Then he said, “Mike, I’m afraid I can’t accept your offer.”

  “Why?”

  “Your wife and son are gone. So you kill Crazy Connor…Is one more body going to make any difference?”

  “In my ledger book, yes. Mr. Nitti, you’re a businessman. I’ve made a good sound business proposal—I’ll work only for you.”

  Nitti stabbed out the cigarette in a tray on the table. “Mike, listen—I respect you. I’d like nothing better than to have you working for us. I know Al will feel the same way—he holds you, and your abilities, in high regard. But you put us in a difficult position.”

  “How?”

  “You said it yourself, Mike. I’m a businessman. Much as I might personally loathe these despicable things that have been done to your family, the alliance between us and the Looneys is a long-standing one…and profitable.”

  “So if John Looney asks for your help—”

  Nitti, impatient now, sat forward. “Let me tell you something you may not have realized. You’ve lived all these years under the protection of people who care about you. And those same people are trying to protect you now. Including me.”

  A chill passed through O’Sullivan’s bones. “Looney’s already come to you.”

  Nitti’s mouth tightened, but his forehead was smooth. “If you go ahead with this thing—if you go through that door of vengeance, you’ll be walking through it alone. And all that trust, all that loyalty we’ve talked about, will vanish…and, Mike, you can’t make it, not on your own. Not with a little boy in tow.”

  This was over. O’Sullivan stood. “You’re already protecting Connor Looney.”

  “We’re not protecting Connor Looney, Mr. O’Sullivan,” Nitti said, still seated, palms up. “We’re protecting our interests.”

  Suddenly the weight of the worst hours of his life fell heavily on O’Sullivan’s shoulders. He could not hide the disappointment in his voice. “I drove through the night to see you.”

  “I appreciate that. I appreciate the respect and trust you’ve shown—that you came unarmed…Now I suggest you drive yourself back to the Tri-Cities. I suggest you go home. Bury your wife and child. With our blessing.”

  O’Sullivan slowly shook his head. “It won’t be that simple…I came asking only your neutrality. But the friend of my enemy is my enemy.”

  Nitti’s eyes tightened. “Are you threatening me, Mr. O’Sullivan?”

  “No. There’ll be no bloodshed today. I don’t think you want the newspapers to have a Lexington Hotel massacre to add to St. Valentine’s day.”

  Nitti shrugged. “You’re free to leave.”

  “Then I will.”

  O’Sullivan went out quickly, his eyes taking everything in as he moved through the reception area to where businessmen were stepping onto the elevator, Marco again playing operator. He stepped on, but then as the doors were about to be closed, thought better of it, and stepped off.

  Down the corridor he found the service stairs and made his way to the lobby, where he blended into the throng of the thankfully busy hotel. Though he sensed no pursuit, he knew he could no longer trust Nitti—honor, loyalty, trust, all of those were old ideas, now.

  But a new idea was forming. So this was all business, was it? Right now, the Capone crowd considered the Looney alliance a valuable asset. O’Sullivan aimed to change that view—he would hurt Frank Nitti, he would make the man bleed…not red, but green.

  When O’Sullivan had left the room, Frank Nitti slipped through a doorway into a small side room, where two men had been tucked away, a mock grillwork vent enabling them to hear every word.

  One of those men, a king in an easy chair, was John Looney, wearing a wrinkled, slightly shabby suit; more snappily dressed, in a chair at his left, sat his son Connor, anxious but sober.

  Nitti approached Looney. “You heard?”

  Looney nodded. To his son, he said, “Go upstairs. I can’t stand the sight of you.”

  Connor sat forward, urgent but rational. “Pa, listen to me. O’Sullivan’s in the hotel right now—you can end this. Mr. Nitti has more guns in this place than the Rock Island arsenal. We’ve got to take him now.”

  The old man shook his head. “In a busy hotel, with the resultant melee?…Connor—go upstairs.”

  Nitti almost smiled; how ridiculous it was, this grown man being sent to his room by his father! By all accounts, Connor was a fairly deadly character; he had been described to Nitti in varying ways, all unflattering: homicidal, unstable, volatile…

  Yet the man wilted under his father’s stare, and finally walked out.

  And when his son was gone, Looney slumped in the chair, his head in his hands. “God help me. God help me…Christ, Frank, what do I do?”

  Nitti took the chair Connor had vacated. “John…try to cast emotion aside. Think objectively. Suppose this O’Sullivan was just another soldier…Not someone you took a shine to, just some bird who got out of line.”

  But the old man only muttered, “God help me…God help me…”

  “You know the answer, John.”

  Looney looked at Nitti with teary, rheumy eyes. “Make it quick, then. Has to be quick. Merciful.”

  Nitti nodded. “Done…and the kid?”

  Dismay exaggerated the old man’s features. “Oh, not the boy! Oh, Christ, no, no…I’ve already lost the wee one…”

&n
bsp; Nitti had about had it up to here, from both O’Sullivan and Looney, with this operatic crap. “Right, fine, sure, and then one day, he’s not a kid anymore, he’s a man. You think Michael O’Sullivan, Jr., won’t remember what your family did to his family?”

  Looney considered that, then shook his head, violently. “Not the boy, Frank. Not the boy.”

  “I understand,” Nitti said, already mulling over who to get for an assignment this important, this hazardous. Someone who had done jobs for the Outfit before, someone freelance but trustworthy, someone worthy of the Angel of Death, someone truly gifted…

  Nitti smiled to himself; he knew just the man.

  NINE

  The true-crime writers call him “the Reporter.” But that seems to be a latter-day appellation: no one has turned up any period reference, either in newspapers or the “true-detective” magazines of the day. This is probably because the public didn’t become aware of Harlen Maguire until his death, after which the press—and later, researchers—put the facts together.

  Maguire was a yellow journalist, and what was called a “picture chaser.” He worked for Hearst papers in several big cities, Milwaukee and Chicago among them, and when a photo was too gruesome even for the tabloid press, he would peddle it to the even more exploitational newsstand crime magazines.

  The gangland beat was his specialty—mob rubouts, in particular, though a good sex scandal or a celebrity autopsy also attracted his particular talent. His stature among the rags he worked for was based on his ability to show up at a grisly crime scene within moments of the carnage going down. He prowled the streets, with a mini-photo lab in his trunk. Some say he inspired the famed New York photographer WeeGee, who took Maguire’s approach to truly artistic heights. Others say he was merely a ghoul with a camera.

  Since no interviews with Maguire exist—and few who knew him, in his daily life, were aware of his dark, private existence—authors have been left to speculate, and dime-store psychology has it that Maguire became obsessed with his subject matter. Others wonder if some of the unsolved murders he “lucked” upon had been his own work—drumming up business, so to speak. An entire book has been devoted to Maguire photos and unsolved murders, with analysis of a certain artistic, ironic staging that may indicate the shooter of the photo was also the shooter of the victim.