Republicans vow to make Illinois the next Massachusetts. Can David Hoffman stop them? Who is this guy, anyway?

Hoffman, 43, told me in a telephone interview between campaign stops on Friday that he and Daley talked politics, what the young man — who had previously worked for U.S. Attorney Patrick Fitzgerald as a prosecutor — might expect running for his first public office.

Daley has not endorsed any of the three major candidates in the Democratic primary, but Hoffman says he’s hopeful that when he wins the primary on Tuesday — Hoffman is not given to self-doubt — Daley and his powerful brothers will endorse him.

Hoffman’s opponents are Alexi Giannoulias, current state treasurer, basketball buddy of Barack Obama, former chief loan officer and vice president of Broadway Bank, founded by his father. The bank has been the source of Giannoulias’s wealth and has allowed him to pursue public office, but it has also saddled him with charges that loans were made to organized crime figures, and to political fixer Tony Rezko, currently in prison and one of the more sordid characters to emerge from ex-Gov. Rod Blagojevich’s (D) administration. Last week government regulators ordered the bank, now run by Giannoulias’s brother, to accept more federal oversight — no more payments to family members without federal approval — and raise $19 million in capital. The third contender is Cheryle Jackson, on leave as president and CEO of the Chicago Urban League, and formerly Blago’s communications director.

Blago goes on trial in June, charged with trying to sell the very Senate seat that these three covet. Its current occupant, Roland Burris (D), was appointed to the seat by Blago shortly before he was impeached. Even Burris, whose ego far outweighs his intellect, realized that he could never win the seat in an election, and thus the opportunity for Hoffman, Giannoulias and Jackson.

Giannoulias has been ahead in every poll, but Hoffman seems to be closing the gap. If he had another month, he probably could, but with the primary looming on Tuesday, he may not be able to close it fast enough.

With both Giannoulias and Jackson having ties to Blago/Rezko and Blago’s trial, scheduled for June, likely making sensational headlines as the November midterms approach, Hoffman is definitely the Republicans’ nightmare. Their candidate, five-term congressman Mark Kirk, is a shoo-in in the Republican primary. He’s also a known quantity, a moderate. If Giannoulias were to win, Kirk could blast him every day, 20 times a day, with his sordid associations. Kirk’s attack on Hoffman would have to focus on the fact that this is his first run for public office, but that’s a benefit in these days of anti-incumbent fervor.

In our conversation, Hoffman returned repeatedly to his clean background. He went after crooks; he didn’t loan them money. “Republicans had already made it clear that they were going to be targeting this seat … because of the corruption issues in the Democratic Party. … It would be very good for us to have someone who took the corruption issue off the table.”

His point was proven nicely when Kirk, a day or so later, said that he believes Giannoulias will win. (He hopes, is what he really means.) As quoted in the Chicago Sun-Times, Kirk exhorted his supporters, “Don’t leave all the glory to the people of Massachusetts — we can do it right here as well.”

Of the campaign in Massachusetts, Hoffman says, Martha Coakley might not have been the perfect candidate but “she certainly didn’t have any baggage tied to some of the corrupt players in the state. … The idea that we as Democrats would nominate someone who allows Rezko or Blagojevich or any of those issues to be brought in by the Republicans is just a really, really bad idea.”

Hoffman grew up on the North Shore, in Winnetka, graduated from New Trier, headed to Yale, where he captained the rugby team — at 5-foot-7 and 150 pounds, “I was always the smallest guy on the field” — then to Washington to intern for Oklahoma Sen. Boren (eventually as his foreign policy legislative assistant at a time when Boren, also a Yalie, was chairman of the Senate Intelligence Committee.). Hoffman went to law school at the University of Chicago, had a clerkship in New York for U.S. Court of Appeals Judge Dennis Jacobs, and a clerkship for Chief Justice William Rehnquist and then on to the crime-busting jobs described above.

A résumé like that would be a terrible thing to waste, and Hoffman, who, like Giannoulias, has family money and has lent at least a half-million to his campaign, has no intention of wasting it.

Hoffman’s maternal grandfather, David Kreeger, was chairman of Geico, and a major art collector who lived in a mansion in D.C. designed by Philip Johnson to showcase his art. Kreeger, who died in 1990, also headed the Corcoran Gallery in Washington, was president of the National Symphony Orchestra, and founded the Washington Opera. Talk about a résumé!

If Hoffman returned to the North Shore, Kirk would be his congressman. But today he lives in Chicago’s trendy Wicker Park with his wife, Monique, of Native American, German, Scottish and Irish heritage, their 2-year-old son, Grayson, and two cats and two dogs.

Monique, a graduate of Mt. Holyoke, was born in Monmouth, in western Illinois, grew up in Alton, worked in the restaurant business — from hostess to general manager of a couple of big restaurants in New York. She and David met while he was clerking for Judge Jacobs. Eventually she moved back with him to Chicago, where she tended bar for five years until the couple’s son was born. She is now a stay-at-home mom.

Win or lose on Tuesday, Hoffman will teach a course in April, once a week, on public corruption and the law at the University of Chicago Law School. When Hoffman was in law school there (1992-1995), Obama was teaching in the legal clinic, but Hoffman never took a class from the future president and says he has never had a “significant conversation” with him — met him only once when Obama was running for the U.S. Senate.

Obama and his handlers, Rahm Emanuel and David Axelrod, have not encouraged Giannoulias, despite his buddy status with Obama. They surely recognize that the link to Rezko could hurt Obama, who made a smelly deal with Rezko in 2005 for land adjacent to the Obamas’ mansion near the University of Chicago.

Two months before Hoffman entered the race, the Obama team summoned to the White House the person they thought had the best shot at keeping this highly symbolic seat. Attorney General Lisa Madigan, put into her job by her father, the Speaker of the Illinois House, Michael Madigan — himself under the microscope for alleged conflicts of interest — was beseeched by Obama himself to run. Only in Illinois, where the typical governor’s retirement home is a prison cell, would a person with Madigan’s baggage (her mysterious, all-powerful father) be considered the top choice.

Late last October, Hoffman took himself to the White House to meet with Obama’s media guru, Axelrod. (One of Hoffman’s first acts as a candidate was to hire Axelrod’s former firm, AKPD, to map and implement his campaign strategy.) Emanuel stopped in briefly, but there was no meeting with Obama. Hoffman clerked for conservative judges — Judge Jacobs of New York remains a close friend — but Hoffman is a self-described progressive. Had he been in the Senate, he says, he would have voted for the healthcare bill, though he was sorry to see the public option dropped. The senators he admires are all progressives — the late Paul Douglas and Paul Simon, and, in today’s Senate, Russ Feingold (D-Wis.).

Some of Hoffman’s opponents have raised doubts that a genuine liberal would have clerked for such staunch conservatives. Hoffman offers me a lesson in how one wins a coveted Supreme Court clerkship. He was advised, he says, to apply to all nine justices. He received one offer and that was from Rehnquist, who, during their interview, did not ask him about his politics. While he disagreed with many of the then-chief justice’s views, Hoffman says, “he was an incredibly, incredibly smart man with virtually an encyclopedic knowledge of Supreme Court cases.” (Rehnquist, Hoffman notes, was No. 1 in his class at Stanford Law.)

The justice he admires most today, he says, is Stephen Breyer.

Hoffman’s parents are divorced, both remarried, giving Hoffman six siblings, two full siblings, three step-sibs and one half-sib. His younger brother, Michael, is a filmmaker in Los Angeles.

His mother’s father, the aforementioned David Kreeger, grew up without much money near Trenton, N.J. — his parents were Russian Jews who came through Ellis Island and owned a small grocery store. Kreeger went to Rutgers as a commuter student, and then got his break when he was admitted to Harvard Law School, from which he graduated, around 1930, No. 2 in his class. He went to New York to apply for jobs at Wall Street firms and was told that none would hire him because he was Jewish. He was practicing with a small firm in New Jersey when a professor at Harvard Law who had gone to Washington to run a New Deal agency called Kreeger asked him to come to Washington. That professor ended up running the Puerto Rican Reconstruction Administration, and brought along his prized student, who was dispatched to the island, where he met Carmen, who would become his wife. The grandson has said that he regrets not having learned Spanish from his grandmother.

Asked for the title of the last book that meant something to him, he says that when he reads at night he prefers fiction and names Cormac McCarthy, and, particularly, The Road, as his favorite. He calls McCarthy “one of the great American writers in the last 50 years.”

While he laments that he doesn’t get home now “at all” to read to his son, he names Grayson’s favorite book as P.D. Eastman’s The Best Nest, a Dr. Seuss-style book: “the mama and papa bird are looking for a new nest and the daddy bird keeps singing” — and then Hoffman breaks into song — “Oh, I love my house, I love my nest, in all the world my nest is best.”

There was, of course, much symbolism attached to “Teddy Kennedy’s Senate seat.” There will be even more attached to Barack Obama’s.

If Hoffman manages a win, or even if he doesn’t, hang on; the race in Illinois will make Massachusetts look sedate.

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