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Incoming White House chief of staff Rahm Emanuel’s career as an investment banker was short but, oh, so sweet. Emanuel left the Clinton White House in 1998 as a senior adviser on a government salary. By the time he won election to the House in 2002, he had earned an astonishing $16 million.

How did he do it?

Partly, it was simple luck: Emanuel dipped quickly into the world of investment banking in time to catch the tail end of the 1990s boom economy as a Chicago-based managing director at Wasserstein Perella & Co., where he worked from 1999 to 2002. While he was there, the firm was sold to the German Dresdner Bank for $1.37 billion in stock, netting Emanuel much of his Wall Street windfall.

Returning to Chicago in 1998 after his White House stint, Emanuel soon ran Wasserstein’s small Midwestern office, developing a reputation as a deal guy who focused on mergers and acquisitions among companies that were subject to heavy government regulation. There, he deployed his skills as a born negotiator who knew the inner workings of government bureaucracies.

Frequently, Emanuel turned big Democratic donors and others he’d met during his White House years into clients for Wasserstein Perella, a firm that was led by Bruce Wasserstein, a hefty financial supporter of Clinton.

Emanuel is “tireless,” said John Canning, a managing director of Chicago-based Madison Dearborn Partners, a multibillion-dollar private equity firm.

Canning became friendly with Emanuel while he was setting himself up in Chicago business circles and has remained close to him through his congressional career. “He’s got a nose for a transaction, a sense for what each party’s looking for and where each party can concede,” Canning said.

Emanuel was unavailable for comment. But in 2003, he described his investment banking career to the Chicago Tribune.

“Fundamentally, I brought in business and worked on business that was very successful,” Emanuel said then. “I didn’t work on one deal. I didn’t work on two deals. I think it was close to six or seven, of which a couple of them were over $1 billion.”

The Democratic congressman from Illinois will be starting out as White House chief of staff for President Barack Obama during a severe global economic crisis. And as a former investment banker himself, Emanuel may be well-positioned to understand the problems and priorities of the nation’s struggling financial system.

While Emanuel lucked into the timing of the Wasserstein sale, the deals he worked on contributed in a significant way to the firm’s bottom line, generating hefty bonuses for him along the way.

One signature transaction was the $16 billion merger of Unicom Corp. and PECO Energy Co. into Exelon Corp., now one of the nation’s largest electric utilities, with nearly $19 billion in annual revenue. The company owns 17 nuclear reactors, which produce about 20 percent of the nation’s nuclear power.

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President-elect Barack Obama (center) during his first press conference, in Chicago, following his election victory, Nov. 7, 2008.

President-elect Barack Obama (center) during his first press conference, in Chicago, following his election victory, Nov. 7, 2008.

It’s proving difficult to peer inside Obama’s still tightly closed Cabinet. But so far his presidential transition has looked deliberate and impressive.

Nov. 11, 2008 | Amid the fervid speculation over the identity of the next secretary of state or even the next assistant secretary of labor for administration and management, there is a truth that is galling to gossip-mongers — Barack Obama and his closest advisors know how to keep secrets. With nearly 10 percent of the transition period between administrations already gone, we know more about the factors that will dictate the selection of the White House puppy than we do about the reasoning behind the choice of a would-be Treasury secretary.

As Valerie Jarrett, co-chair of Obama’s transition team, put it with deliberate blandness on “Meet the Press” Sunday: “I think one of the real strengths of Sen. Obama’s campaign and now President-elect Obama’s transition is that he really does like to think this through thoroughly and not telecast what he’s going to do until he’s ready to make a decision.”

No one wants to read articles titled “Entire Obama Administration Shrouded in Mist and Mystery.” So to accentuate the positive, we do have a pretty reliable handle as to who will be in the room with Obama (and presumably Joe Biden) when the major personnel decisions are made. There will be Jarrett, an African-American Chicago real estate entrepreneur who has been close friends to the president-elect and the incoming first lady for two decades; Pete Rouse, the press-shy former chief of staff for Senate Majority Leader Tom Daschle, who performed the same role for a newly elected Illinois senator named Obama; the Chicago-born John Podesta, Bill Clinton’s former White House chief of staff, who stealthily organized the Obama transition during the fall campaign from his Washington perch at the Center for American Progress; David Axelrod, the Chicago-based political strategist, who was the inspiration behind both Obama’s up-from-nowhere 2004 Senate victory and his 2008 run for the Rose Garden; and incoming White House chief of staff Rahm Emanuel, a sharp-elbowed veteran of the Clinton White House who was elected to Congress in 2002 (from Chicago, natch) with the help of Axelrod (double natch).

With all these Chicagoans (aside from Rouse) creating the Obama administration, it is time to drop the Second City urban inferiority complex. If there is an ideological orientation to this team, it seems to be Democratic centrism rather than full-throated liberalism. Bill Galston, a former top domestic advisor to Clinton now at the Brookings Institution, notes that Obama “has a great respect for expertise. His instinct is that in any field, gather the leading experts and go after them.” As Galston puts it, “This is not amateur hour — this is not crony time.” Paul Light, a professor of public service at New York University and an expert on governmental organization, said admiringly, “Obama is extremely well-prepared. There is a lot of talk coming out of the Bush administration about a seamless transition. But in many instances, the Obama people know as much about what is happening in the Cabinet agencies as the Bush people do.”

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Colleagues coined a phrase during the Clinton years to fit Emanuel's ability to mangle the English language. AP

Colleagues coined a phrase during the Clinton years to fit Emanuel's ability to mangle the English language. AP

Newly coined Obama chief of staff Rahm Emanuel was on his best behavior during his Sunday show debut this weekend – measured, calm, bi-partisan.

But when it came to the notorious ability of the Illinois political street fighter to mangle the English language – well, let’s just say Rahm hit a touchdown.

Friends and colleagues – particularly in the Clinton White House – have dubbed this phenomenon “Rahmbonics” over the years and on “Face the Nation” and “This Week,” Emanuel engaged in a veritable festival of mixed metaphors.

The jumbling began during a discussion of how Washington leaders have put off dealing with energy issues since the oil crisis in 1974 and health care for nearly just as long.

“We had a crisis, we kicked it down the can,” Emanuel explained to “Face the Nation” host Bob Schieffer.

“These are – just taking those two examples, these are crises you can no longer afford to kick down the can,” he continued. “The crisis we have here, the American people know we have one and they are ready and willing to start to tackle those problems. You cannot afford now to kick those down the can any longer.”

To which Schieffer simply replied, “All right,” and moved on.

“Kicking the can down the road” has been a favorite metaphor politicians have used to describe someone who is postponing a decision or avoiding an issue.

But Emanuel’s Yogi Berra-style translation of the phrase should come as no surprise to those who know him well. Speechwriters in the Clinton White House, where he was an aide, used to collect choice examples of “Rahmbonics” and post them on a bulletin board. Oftentimes they involved sports.

“He’d say something like you can’t kick a field goal in the ninth inning,” recalled Jake Siewert, a longtime friend as well as a former Clinton press secretary and longtime admirer of Emanuel’s verbal skills.

Shutting a revolving door was another Emanuel classic. He used the phrase in 1998 to explain a Clinton plan to require states to report illegal drug use among inmates before receiving federal money for prisons.

“We have to slam shut the revolving door between drugs and crime,” he told The New York Times.

“We kept tabs on them,” said a former Clinton speechwriter who asked not to be named. “There was a certain kind of admiration in involved in this.”

The mix-ups that made it into newspapers, as opposed to those he blurted out in staff meetings, were the ones that intrigued Emanuel’s White House colleagues the most.

Quoting Emanuel-style metaphors even became a game among some members of the Washington press corps.

“You figure if he’s quoted in the newspaper he’d given it more thought,” said Siewert, adding that Emanuel has a sense of humor about his way with words. “He’s pretty well aware of it. I mean he thinks fast and talks fast.”

Emanuel’s appearances last Sunday made clear his metaphor mixing is a treat the public will get more of in coming months.

Despite the disorienting image of “This Week” host George Stephanopoulos addressing his longtime friend and former Clinton White House colleague with the formal “Congressman Emanuel,” Emanuel kept familiar when he attempted the “kicking the can down the road” line again in reference to energy, health care and economic crises.

“So this provides an opportunity to finally tackle the issues that for too long have been postponed, kicked down the road – kicked down the road, basically,” he said.

He also suggested bridging the auto industry, when discussing government’s role in helping country’s struggling car manufacturers.

“President elect Obama has asked his economic team to look at different options of what it takes to help bridge the auto industry,” he said. “So they are part of not only a revived economy but part of an energy policy going forward.”

So, to sum Emanuel up: don’t expect an Obama administration to let the clock run out in the final quarter when the bases are loaded – even if the blitz of crises facing the country makes them want to kick the road down the can.

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