On that Sunday, the last day of last year’s Printers Row Lit Fest, Scott Jacobs stopped at the Chicago Literary Hall of Fame tent to see me. He had an advance copy of his new book in hand. He was drumming up interest—he always had a project or ten in the works. He was a doer. A hustler. A friend who relied on friends and did things for friends. He handed me the book. “Take this,” he said.
He looked me in the eye. “If you think it’s worth writing about… hummm. Or just read it.” Scott’s pregnant pauses were filled with these sly, inside-joke type singsong noises. The music of a hustler speaking to his people, all, in their own ways, hustlers themselves.
With Scott, there was never an ulterior motive. He straight-out told you his motive. He’d self-published five books already, under the cover of his own Dead Tree Press. For his three political books, he used the pen name Stump Connolly.
This new book, “I Told You So! Donald Trump, The Awful Years” was another Stump Connolly title, and I already knew about it. He’d called soliciting advice on how to make this one outperform his previous titles, which, like nearly all self-published books—even the truly outstanding ones—lived short, uncelebrated lives. And make no mistake: these were outstanding books. Scott was a great writer. His political analysis was astute, original and incredibly insightful. His style reflected his own giddy interest in the realm. He loved the game: its stupidity, its arcane notions, its corruption, the cult of personalities, the bizarrely intense emotions. He loved it all, the blemishes especially. He’d covered six presidential campaigns, often without sponsorship, dealing and cajoling his way into press badges, cheap lodging and access to the people who would be his stories. I always pictured “Sullivan’s Travels” with Scott—make that “Stump”—playing the lead in one of those fedoras festooned with a gaudy “press” card. He grasped, always, the irony and contradictions and hypocrisy, and reported on them without rage or condescension or self-importance. He had an even-handed analytical style that was charming, funny and smart. His own fascination with the subject came across clearly as he pierced through all the nonsense to get at the real meaning and ramifications imbedded in a story.
His other books, his Scott Jacobs books, were likewise fun and worthwhile, and in those he demonstrated his abiding affection for people and places, often Chicago people and places. Once, we got to talking—he was working on “Never Leave Your Block: Adventures in Urban Living”—and it turned out he was doing a piece on my barber, Joe, a longtime fixture in Logan Square. We swapped stories about Joe and the barbershop. I asked him if he’d been there around the holidays, when Joe put out jugs of his Italian garage wine. They were, of course, for sale, as was most everything in Joe’s—he played 8-track tapes as a teaser for customers interested in their purchase, and displayed used bikes he was trying to unload. “I’ve got almost a whole jug left over from last Christmas,” Scott guffawed. His laugh started with a kind of honk and sped into a bullet spray of squeals, a laugh that should have been trademarked or used by a “Simpsons” character. “Not bad. Hum, a, hummm. Not good.”
So I knew all about Scott’s book and genuinely looked forward to reading it. I’d put him in touch with a couple of friends and he’d hired them to help him do advance publicity. He and this makeshift team had sent around at least fifty review copies. He’d ordered an initial press run of a thousand copies, soon to land on his doorstep on Medill Street. Scott felt this was his best book and also the book that stood a chance at gaining some kind of traction. He felt it: this one would break through.
As we stood there, we laughed—Scott might have blocked out his weekend to pitch his book, but at the core he just wanted to talk, and listen. I won’t say he loved people because he despised some of them. Though he was from Wisconsin, Scott possessed that Chicago radar for the disingenuous, the selfish, the moronic, and he seemed incapable of hiding his distain. I once thought Scott’s brutal honesty was a flaw, an unkindness, perhaps unnecessary, but over the course of nearly two decades I came to understand that this was another winning trait. He cared enough to say what he felt. When we were first launching the Chicago Literary Hall of Fame, we held a town hall-style meeting to gather thoughts, ideas, and so forth. As in many literary gatherings, the people there were incredibly supportive, nice, but Scott played the role of contrarian. “You don’t want to do this, Don. A nonprofit means, ‘NO PROFIT.’ This is going to take years. What will YOU do for money?” The friendly literary sorts formed a mob against Scott and his thumbs down, but he didn’t seem to care. You could take Scott’s advice or not but know that what he offered was sincere. Mostly, he was right about things.
There in the sunshine of a pleasant mid-September Sunday, we went on like that for a while. The festival was surprisingly packed, considering we were inching to the end of the weekend, a time when in past years vendors started to put away their flyers, bag up their giveaway buttons, crate their books and generally fade out. Scott still had some slinging and pitching to do. I was holding his book. We shook hands and he scooted into the crowd. As I started to put Scott’s book in my backpack, Barry Jung, my erstwhile CLHOF volunteer who knows all about my extensive Chicago collection, asked, “Did he sign it?”
I checked. Nope. I scurried from behind our table and sped toward the juncture at which I’d seen Scott walk. He’d left only a minute before. I looked this way, then that. There were too many people. I thought maybe I’d spot Scott’s snow-white hair and catch him, but I wasn’t sure which direction to pursue. I paused at the corner of Dearborn and Harrison, holding “I Told You So!: Donald Trump, The Awful Years.” I thought, “That’s okay. We’re getting together in a week or so anyway.”
That was the last time I saw Scott Jacobs.
When I learned, via an email that contained a link to his obituary, that Scott had died on October 21, of a heart attack, I had just called his cell phone. We’d been on the phone several times since the Lit Fest. He’d wanted to brainstorm on places to do his book launch. He knew all about the places I’d done mine because he was there for them, all of them. That was another thing about Scott: he showed up. He came out to the Hideout when my novel launched, Murphy’s Bleachers for my Cubs anthology, the Cliff Dwellers for my short-story collection. These were events that were more important to me than to anybody else. Scott knew they were important and made sure I knew he thought so, too. At these and other occasions, including many CLHOF events, I’d look across the room to see Scott propped on a bar stool or at a table, drink in hand, looking, for all the world as if there were absolutely nothing else going on in his life but THIS.
We’d last spoken a few days prior. I’d picked up the phone while driving to my son Dusty’s flag football game. I’m hesitant to use the phone while driving, but put it on speaker just so I could let Scott know we should talk later. He said, “Go, go. Get to Dusty. Nothing urgent. Call whenever.”
He finished with what at the time seemed like a general nicety, cliché even, but in retrospect proved a bit haunting. He said, “I’m not going anywhere.”
By then I’d read Scott’s book and loved it. I meant to tell him that. I meant to tell him that he was right, this was his best book yet. I’d especially wanted to share my enthusiasm for the blunt analytical pieces, like an early chapter titled, “Our Mussolini,” which contained the opening: “There is no fair and balanced way to say this. The acceptance speech Donald Trump gave at the Republican Convention Thursday night was the most frightening piece of demagoguery I’ve ever heard in politics.” In the essay, which was written in 2016, Scott goes on to dissect all the malarkey (a subtitle in the essay) Trump spewed to his fawning public.
The book is structured as a series of chronological essays dated at the time of their original publication. It’s a riveting trip through an expert political observer’s immersion in an era that he knows is going to be real bad. It’s a time capsule of the Trump presidency, the Trump phenomenon, and the forces competing to unravel and save American society. Scott’s clarity is impressive, as in the chapter “Hate vs. Fear,” in which he writes, “His interest in the presidency will end the moment he wins it. Oh sure, he’s got a few ideas on how to redecorate the White House, and it’ll be fun watching him negotiate a trade deal with his new best friends in Mexico. But his ignorance of foreign policy is manifest. He has no patience for dealing with those losers in Congress. There is nothing in the Constitution that lets him declare bankruptcy if his plan for America turns out as riddled with false promises as his casinos in Atlantic City. And God knows what he’ll tweet out at 3am while he’s up waiting for Putin to call.”
I’d meant to compliment the wit, thinking of laugh-out-loud lines like, “It’s heartening to watch The Washington Post and New York Times in a good old-fashioned newspaper war over who has the latest, and deepest, sources in the Russian investigation. It’s comforting to see congressional committees investigating high crimes and misdemeanors, not cleaning out Trey Gowdy’s smelly sock drawer of inferences.”
And the clever chapter titles, like, “The Salesman in Chief,” “I Am a Rock, I Am an Island, I Am an Idiot,” and “Watch Out for That Flying Bag of Dope.”
I’d also wanted to point out what a feat he’d achieved in writing an anti-Trump book from the perspective of somebody clearly willing to entertain the other side of the story, a dynamic that is underscored in the book’s sidebars about his ultraconservative upbringing, his documented record as a true independent, and his up-close poll-watching views of the Chicago Democratic machine’s historical corruption.
Mostly, I’d wanted to tell him how this book was the culmination of his life’s work, from his student days as a Harvard Crimson reporter, to his writing for The Milwaukee Sentinel and Chicago Sun-Times, through his early embracement of new technology that led to the founding of Chicago’s Center for New Television and IPA, The Editing House, and his popular internet column, “The Week Behind.” Scott had spent more than a half-century absorbed in the minutiae of politics, media and society, relentlessly honed his reporting skills and writing craft, and ever solidified his deep intellectual bona fides. Only such a highly trained and informed political junkie could have so seamlessly pieced together the characters, issues, statistics, reactions and meaning of this story. So much had been written about Trump it seemed unlikely that anybody could add something significant to the warehouse of thought. But he’d done just that.
On the cover of his book, Trump is pictured at a podium while Scott, glasses sliding down to the tip of his nose, is in the foreground, saying, via a captioned balloon, “I Told You So!” Indeed, Scott knew so much of what was to come before it happened.
But this, his end, he couldn’t have known. In the greeting line at his St. Hedwig’s service, his lookalike brother, Bruce, said, “It was quick and painless.” That’s something, for sure. The line stretched all the way from Hoyne Avenue to the nave. Must have been 250 or 300 mourners. I wasn’t surprised so many people turned out. Scott made real connections to people over a long time. I first met him through our mutual friend George Rawlinson. We’d both been invited to attend the authors fair that George had organized at the Elgin Public House. By chance, we were seated next to each other. Attendance was light, so we spent half-a-day just talking. Every now and then, somebody would pop by and declare, “Scott!” All the way in Elgin he knew people.
There’s something unsettling whenever a friend dies. Maybe it’s just that dreadful feeling that he was just here, right here, and now… He’s gone. In Scott’s case, that dreadful feeling is amplified by the fact that he died before his book could be born. Here it is, in utero.
At the service, I ran into the great director, Jim Sullivan, who’d likewise been engaged in a project Scott had conceived. Jim was the first of many to exclaim what a tragedy it was that this book might die with Scott. Others during the service did the same.
But literature is immortal, or it can be, so long as there are ways and means to access it. Scott’s book, it turns out, will come out as he planned. I helped the family organize a launch event on March 2 at The Cliff Dwellers. That night will be as much a celebration of Scott’s life as a release of “I Told You So!: Donald Trump, The Awful Years.” It’s likely that a great number of people will be there and that they will buy his book. This would have been just Scott’s kind of thing, something to marvel over. I can almost hear his voice, almost write the joke for him—“Dead Tree Press? More like Dead Guy Press, Don.” Then the honk, the signature burst of laughter. Why not? Scott enjoyed the ridiculous. As he wrote in the jacket liner of his new book, “I hope we can look back someday and appreciate the absurdity of making a man like that the leader of the free world.”
“I Told You So!: Donald Trump, The Awful Years” book launch, Wednesday, March 2, 5pm-7pm at The Cliff Dwellers, 200 South Michigan. Register here.
“I Told You So!: Donald Trump, The Awful Years” By Scott Jacobs Dead Tree Press, 282 pages
Donald G. Evans is the author of a novel and story collection, as well as the editor of two anthologies of Chicago literature, most recently “Wherever I’m At: An Anthology of Chicago Poetry.” He is the Founding Executive Director of the Chicago Literary Hall of Fame.
