In banking, Rahm Emanuel made money, connections

“I had this idea that this would work and had upside,” said Wasserstein, now chairman and chief executive of Lazard, the investment bank. “It worked out better than I could have hoped.”

And better than Emanuel could have imagined as well. Over the course of a three-hour dinner, Simpson and Emanuel discussed how they might work together. Shortly afterward, Emanuel accepted an offer, nudging him down what has by now become a well-trodden gilded path out of politics and into the lucrative world of business.

Emanuel, who decided last month to leave his House seat and become Barack Obama’s White House chief of staff, went on to make more than $18 million in just two-and-a-half years, turning many of his contacts in his substantial political Rolodex into paying clients and directing his negotiating prowess and trademark intensity to mergers and acquisitions.

The period is a little-known episode of Emanuel’s biography. Former colleagues said the insight it afforded him on the financial services sector is invaluable especially now. But Emanuel built up strong ties with an industry now at the heart of the economic crisis, one that will be girding for a pitched lobbying battle next year as the incoming Democratic administration considers a potentially sweeping regulatory overhaul.

After Emanuel left banking, members of the securities and investment industry became his biggest backers, donating more than $1.5 million to his campaigns dating back to 2002, according to the Center for Responsive Politics.

Emanuel also leaned heavily upon the industry while he was chairman of the Democratic Congressional Campaign Committee during the 2006 midterm elections. Financial industry donors contributed more than $5.8 million to the committee, behind only retirees. Friends of Emanuel’s from his private-sector days said he still checks in with them regularly to plumb their insights on economic issues.

“He asks me what am I seeing, what business is like, what’s the climate, where are the weak spots,” said John A Canning Jr, chairman of Madison Dearborn Partners, a Chicago private equity firm that is in the same building as Wasserstein’s offices.

Canning was one of many financial executives Emanuel met with soon after he left the White House to discuss job prospects, with Emanuel’s political connections often opening doors.