WASHINGTON -- Quick, who headed the Commerce Department under President George W. Bush? 

No disrespect to Carlos M. Gutierrez, but commerce secretary is not one of Washington's more glamorous jobs. It's overshadowed by first-tier Cabinet posts at Justice, State, Defense and Treasury. Scores of senators, House members, Supreme Court justices and White House aides would draw more attention at a Georgetown cocktail party or DuPont Circle restaurant. 

But the job is giving a disproportionately big headache to President Barack Obama, who now must try a third time to fill it. Don't be surprised if he picks a lower-profile nominee, because his two rather ambitious choices have backfired. 

Obama first tapped New Mexico Gov. Bill Richardson, a Democrat who gained national attention with his 2008 presidential bid. Richardson withdrew amid a federal investigation of state contracts won by a politically connected company. 

Then Obama turned to Republican Sen. Judd Gregg of New Hampshire. Though not a national figure, the taciturn Yankee is a player in the Senate. A former Budget Committee chairman, he is liked by colleagues and known for unemotional, no-nonsense analyses of fiscal matters. 

Gregg stunned colleagues late Thursday when he withdrew his name, citing "irresolvable conflicts" with Obama's handling of the economic stimulus and 2010 census. 

Click here for our video coverage of Sen. Judd Gregg. 

In Richardson and Gregg, Obama sought appointees whose public and political backgrounds arguably made them a bit overqualified for the job. Bush, by contrast, went with friend and fundraiser Donald Evans for his first term, and then Gutierrez, who had made his name in the private sector as chief executive of Kellogg Co. 

Obama also had politics in mind when tapping Richardson and Gregg, and neither plan worked out. Richardson is a prominent Hispanic, an ethnic group increasingly important to both parties. 

And Gregg, a lifelong Republican, would have helped Obama fulfill his promise of building a truly bipartisan Cabinet. 

Richardson's and Gregg's long records in public office, however, also made them more susceptible to the types of problems that ended their nominations. A governor must walk a careful line in awarding state contracts. And a veteran senator must answer to partisan supporters and loyalties that don't affect a corporate CEO. 

Over the long run, Obama's difficulty in filling the Commerce post may prove little more than a time-consuming distraction when he needs to focus on the economic crisis. 

"Let's be honest," White House Chief of Staff Rahm Emanuel told reporters Thursday night. "Will the economic recovery or Judd Gregg be a bigger discussion point a week from now?" 

Still, the episode may offer a few glimpses into the president's judgment and ambitions. 

Especially with Gregg, a down-the-line conservative Republican, Obama took a gamble by inviting a potential naysayer into his inner circle. If critics want to portray Obama as misguided or opportunistic, they won't get much help from Gregg. 

Obama has "aggressively reached out across the aisle, and I immensely respect that, and I immensely respect him," Gregg told reporters after withdrawing his nomination. "And I know he's going to be a strong and effective and good president." 

He is a president, however, trying again to fill a Cabinet post that rarely crosses the minds of millions of Americans.