President Barack Obama’s new chief of staff wasn’t always so confident about his new boss — William Daley donated to Obama’s 2004 Senate primary rival Dan Hynes.

Daley gave Hynes $922 in 2003 and $5,000 in March 2004, about 10 days before the primary. But Obama won the nomination and spoke at the Democratic National Convention. Daley gave Obama $2,000 in July 2004 and $1,000 in September, according to campaign finance records. Later, Daley contributed to Obama’s political action committee and to his presidential campaign.

Over the years, Daley has donated thousands of dollars to Congressional candidates across the country. He’s helped Democratic leaders, giving donations to House Minority Whip Steny Hoyer (Md.), Assistant Leader James Clyburn (S.C.), Senate Majority Leader Harry Reid (Nev.), and Sens. Charles Schumer (N.Y.) and Dick Durbin (Ill.). But campaign finance records dating back to the 1970s did not show any donations to Minority Leader Nancy Pelosi (Calif.).

Daley did not have the best track record in the last cycle, donating to multiple losing candidates in a cycle that was not kind to Democrats. Of the candidates he donated to in the 2010 cycle, just Sen. Kirsten Gillibrand (N.Y.) won her race. He also gave to losing Democratic Reps. Melissa Bean (Ill.), Michael McMahon (N.Y.) and Scott Murphy (N.Y.) and to Sen. Blanche Lincoln (Ark.), who was one of two Democratic Senators defeated in November.

The incoming chief of staff has already shown a bipartisan reputation, donating to Sen. Kay Bailey Hutchison (R-Texas) in 2004 and former Speaker Dennis Hastert (R-Ill.) in 2002 and 2005.