If incoming White House chief of staff William Daley had his way in 2004, his new boss would never have made it to the US Senate, much less the Oval Office.

Daley, an executive at JPMorgan Chase and a longtime veteran of Democratic politics, contributed to President Barack Obama’s primary opponent in 2004, the year he sought election to the US Senate.

Election records show that Daley gave Obama’s rival Dan Hynes $5,000 less than two weeks before the Democratic primary, and $922 the year before. But the loyal Democrat proceeded to support Obama after he won the nomination, and donated a total $3,000 to his campaign in the three months after he keynoted the Democratic National Convention.

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The donation was revealed Thursday by Christina Bellantoni of Roll Call, who notes that Daley has contributed to a multitude of Democratic campaigns and has even given to two Republicans, Sen. Kay Bailey Hutchison (R-TX) and former Speaker Dennis Hastert (R-IL).

Daley’s attempt to defeat Obama, whose campaign for Senate and record in the Illinois legislature entailed solid progressive credentials, may reflect the Third Way board member’s business-oriented nature and aversion to liberal stalwarts. Hynes has defined himself as a more “moderate” liberal.

The reaction to Daley’s appointment to the high-powered job has been mixed. It was lauded by the Chamber of Commerce, America’s preeminent business lobby, and met with skepticism by progressives who lament that it merely enshrines Obama’s corporate-friendly approach to governing as president.

The move, some pundits surmised, was also crafted as a shield against Republican claims that Obama is an anti-business president.

The New Republic‘s James Downie recently recalled a minor clash between Obama and Daley in the early 2000s. Daley was hired by SBC Communications to lobby for industry-backed telecommunications legislation decried by liberals as anti-consumer.

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Obama, an Illinois state senator at the time, opposed the effort, remarking: “Ramrodding bills through because you’ve got the clout to do so—rather than because you’ve got arguments on your side—is not a good way to do the people’s business.”