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“I don’t run on the presidential program of saying that if I am elected, life will be easy,” Kennedy declared, his voice booming off the surrounding high-rise buildings. “I think to be a citizen of the United States in the 1960s is a hazardous occupation. But it is also one that offers challenge and hope, and I believe the choice lies with you on November 8.”
“Whether I am the candidate for the presidency, or president, or stay in the Senate, I regard our obligation not to please you but to serve you, and in my judgment, in 1960, a candidate for the presidency should be willing to give the truth to the people, and the truth is that what we are now doing is not good enough.”
I somehow absorbed the larger message: we are the masters of our future, and politics is the means by which we shape it.
Fifty-two years later, on November 5, 2012, I stood at the foot of the stage at another huge, outdoor rally, on the eve of another presidential election. It was 10:00 p.m. in Des Moines. A crowd of twenty thousand stretched from the podium on Locust Street four blocks east toward the glistening gold dome of the Iowa state capitol. They waited for hours, on that chilly November night, to watch President Barack Obama deliver the final speech at the final campaign stop of his political career—and mine.
Obama placed his bet on Iowa and the army of idealistic young people who descended upon the state, hell-bent on changing the course of history. And without Iowa’s embrace, his candidacy almost certainly would have died a quick, snowy death.
But whatever doubts Obama harbored were matched by a preternatural sense of competitiveness. This man hated to lose a game of H-O-R-S-E, much less an election that would define his presidency. So he fought his way back, knowing what defeat would mean for his programs, his legacy, and for the millions of young black Americans for whom his election had opened new vistas. And he believed the stakes for the country were large.
“Yes We Can.” It was the tag line I had written for the first TV ad of our first, long-shot campaign together just eight years earlier, when Obama, a largely unknown and seriously underfunded state legislator, set out to win a seat in the U.S. Senate. And it became our mantra when, in 2007, he enlisted millions of Americans to the cause of change.
In 2008 we had built a once-in-a-generation movement for change. In 2012 we simply ran a very proficient political campaign.
Moreover, after more than 150 campaigns, I had to acknowledge the physical and emotional toll they had taken. Campaigns are at once exhilarating and exhausting. For the campaign “guru” (the driver of the strategy), they require the projection of utter assurance, even as you constantly wrestle with uncertainty. They dominate your life and infiltrate your mind, even when you’re sleeping (which is rare).
We think that we can escape the pathologies of our past, but too often that turns out not to be true. My mother was scarred by her upbringing, and without malice or the least trace of self-awareness, she passed the virus on to me.
Then, on November 22, 1963, Kennedy became the first American president to be assassinated in the television age. When the shocking news came, we were dismissed from school.
From that day on the mailbox, I was obsessed with all things Kennedy. Even as a small child, I heard JFK’s call. I believed him when he said that, together, we Americans could chart our future and change the world, and that we each had a role to play. I was intrigued from the start by the game of politics and the larger-than-life players it attracted. I also sensed that it was about big, noble ideals. It was about history and historic change.
Bobby Kennedy had emerged from a period of mourning and reflection as a fierce and fearless advocate for change and reform.
Bobby Kennedy had challenged a failed status quo, mobilizing millions behind an inspiring campaign for American renewal to which he had given his all. Had he lived, I am convinced he would have defeated Nixon, and changed the course of history for the better.
order. “If you run, we need to be as bold, and rekindle that kind of hope.”
Bobby was an authentic crusader, fighting for things larger than himself. Andy was ambitious for himself, not for a cause—a synthetic candidate saying and doing whatever it took to win. It was my first exposure to politics as a business rather than a calling.
The University of Chicago was a highly regarded institution, and far enough from home, a teacher reminded me, that my parents would never surprise me with a visit. For me, there was another attraction: Chicago had the most interesting politics of any major American city.
had played a critical role in electing John F. Kennedy president. But his roughhouse tactics in dealing with unrest in Chicago’s black community, and fallout from the calamitous 1968 convention, had thrown a serious wrench in the Daley machine. With politics as a big lure, I packed my bags and headed off to Chicago. I would never return.
The U of C, then as now, had distinguished graduate schools, known for their erudition and Nobel Prize–winning scholars, but the undergraduate college at that time was more of an afterthought, with scant campus life. It was a wonderful school for highly motivated students who were not looking for much more than great professors and an outstanding syllabus, and many of my classmates came eager to settle into the monastic life of the scholar. I did not. I was not the typical U of C freshman. I was still very much the hyper kid, smart enough to get by, but too distracted to sit still for hours
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The Villager’s misfortune was my opportunity. Desperate for help, they offered me a fifty-dollar-a-week internship to augment their bare-bones operation.
The long summer also gave me a chance to spend more time with my dad, who, for the first time, hinted that he was struggling financially. One night, when we were out to dinner, he asked if the paper needed an advice columnist. “You know, it would be really helpful if I could pick up a few extra bucks,” he explained, with a trace of embarrassment. “You think they might have any interest?” My dad was paying my tuition, and I knew he was helping to support my grandmother and her sister. Yet it was only then that I began to understand that he was really stretched. Later, I learned that he also had
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Metcalfe became a local hero after running alongside Jesse Owens at the 1936 Olympics in Hitler’s Berlin and returned home to become a cog in the Democratic machine. But in 1972, he broke from Daley after one of Metcalfe’s constituents, a respected South Side dentist, was stopped and grievously mistreated by police officers for the apparent crime of being black, a not-infrequent occurrence in Chicago. Metcalfe was soon calling for an independent civilian agency with the power to investigate alleged incidents of misconduct. In the column, I analyzed a recent speech by the mayor condemning
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Democratic machine—though only after both Daley and Metcalfe had died. It would also lead to the election of Chicago’s first black mayor, Harold Washington, and provide the base for the meteoric rise in Illinois politics of Barack Obama.
unforgiving light on corruption and racial discrimination in Chicago.
The target of Despres’s attack, a crusty, old ward boss named Vito Marzullo, shook his fist in rage, uttering expletives in two languages. A decade later, when Despres was shot in the leg while on his way home from a late night of work, Marzullo offered a tart observation that probably summed up the feeling of many council members: “They aimed too low.”
Ben Lewis, won a special election in 1958, the handpicked designee of the ward’s real power: a Democratic boss named Erwin “Izzy” Horwitz. In 1963, Lewis was shot to death in his ward office. His bodyguard, George Collins, who said he had gone out for a smoke when Lewis was murdered, succeeded him as alderman and later rose to Congress. When Collins, in turn, perished in a plane crash in 1972, his grieving widow, Cardiss, visited Mayor Daley to propose herself as her husband’s replacement. As the legend goes, Daley gently explained to Mrs. Collins that he had another candidate in mind. “Mr.
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(King claimed that the racism he encountered in Chicago was more “hateful” than anything he had encountered in the South.)
Of course, the time I spent in a dark room reviewing records at the County Building was time I wasn’t spending in class or at the library. I wish I could retake some of the courses I sprinted through then, doing only enough work to get by with decent grades. The education I was offered was far better than the one for which I settled. But I was a young man in a big hurry. I had found a calling, and the best preparation for it was on the street, not in the classroom. I loved politics, and I loved reporting, but I pursued journalism relentlessly for another reason. In the spring of 1974, I got an
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Whenever I was hurting or anxious and felt as if there were nowhere else to turn, Dad was there for me with soothing, sensible advice and a warm, loving, always comforting smile. “It’ll be all right, boy,” he would tell me. “It’ll be better tomorrow.” And it almost always was, but would it now? Would it ever?
He didn’t leave a note, but there was no doubt that the financial burdens Dad had hinted at the previous summer were a constant concern. He had taken on the extra work doing testing at the settlement house, but had performed badly and was fired, evidence that this bright, talented man was no longer quite himself. I’ll never know the whole story, but I believe it was this desperation coupled with a sense of failure that drove Dad to hang himself in the sterile little studio apartment in Midtown where he and I had spent so many nights.
Dad left me seventeen thousand dollars, an old Plymouth Fury, and a broken heart. I was angry with myself for missing the clues, and angry with him for not seeking help. A mental health professional, he had saved the lives of others, but was apparently incapable of reaching out to save his own.
For years after his death, the anniversary announced itself to me through bouts of depression and self-doubt. What did it say about my fate that the man I so admired could end up ...
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Though my colleagues were all different, most shared one quality: an unquenchable thirst for a good yarn. They viewed reporting as a calling. As products of one of America’s most competitive newspaper towns, they lived to get it first and to get it right.
Only it wasn’t 1960. Between the scars of Chappaquiddick—where, in 1969, a young woman drowned in Teddy’s car after he drove off a small bridge and fled—and the growing sense of alienation from liberal Democrats among Chicago’s ethnic Catholics, the youngest Kennedy brother was bound to face a tough road. And, as it turned out, Byrne’s imprimatur became more an albatross than a boon.
“I am running to end Jane Byrne’s four-year effort to further institutionalize racial discrimination in this great city,”
I deeply believed. And for all the bashing back and forth, we won in the end by appealing to hope; by projecting the ideal of one American community in which everyone gets a fair shot. That’s what Simon believed, and by forthrightly expressing it, he defeated not just an opponent on the ballot, but also the cynical political calculus of the day.
Every race is different, but the protocol is the same: Understand fully the array of arguments that could be made for and against your candidate, test them in polling, and cull the two or three that are most meaningful and that will have the greatest impact on the targeted voters you need to win. Then weave those arguments into a larger, authentic narrative that communicates who your candidate is and why he or she is running.
presidential elections ever since. When incumbents step down, voters rarely opt for a replica of what they have, even when that outgoing leader is popular. They almost always choose change over the status quo. They want successors whose strengths address the perceived weaknesses in the departing leader.
They want successors whose strengths address the perceived weaknesses in the departing leader.
Yet as the race wore on, he grew into this more contentious role of advocate, challenging the status quo on behalf of the forgotten New York—and became more genuine in identifying himself as part of it.
“What do you think he meant by that?” Freddy asked, recounting the story. “‘You’re not from here.’ The hell with that. Let’s win this thing.”
My dad “wasn’t from here,” but he came because of the promise of America, and as its barriers fell, America grew stronger.
trying to live up to the legacies and demands of a parent, or compensating for one’s absence.
Susan’s illness was a wakeup call. We were mortal; we would not live forever. We
Our challenge was to persuade a skeptical political and donor community that a little-known black man with an alien name and unproven campaign skills—a man who just a few years earlier had been trounced by Bobby Rush—could topple a formidable primary field.
He was idealistic in his aspirations, but pragmatic in pursuit of them—ready and willing to do what was necessary to advance his political and legislative goals.
“No, you don’t get it,” Obama said. “These folks? They’re just like my grandparents from rural Kansas. I talk about my grandfather, and how he marched in Patton’s army. And I talk about my grandmother, who was a Rosie the Riveter. And we have a great time.”
empathy.
The final bill required police to keep records of every traffic stop, including the race of the motorists, and submit these to the state. It also mandated sensitivity training for police to reduce incidents of profiling and needless
Beyond those victories, however, was a larger portrait of Obama, who pursued progressive goals in a pragmatic way.

