WHEN YOU'RE IN OVER YOUR HEAD DON'T DIVE DEEPER:

Organizing the White House Is Obama's First Test: All presidents come to realize how much structure matters. (KARL ROVE, 12/18/08, Wall Street Journal)

Mr. Obama's new Health and Human Services (HHS) Secretary, Tom Daschle, has never run anything but will have responsibility for one of the government's most complicated departments. And while Mr. Daschle may have lost his last campaign, he's lost none of his skill at internecine warfare. The wily Washington insider also grabbed the title of director of the White House Office of Health Reform. The creation of this new Daschle-led office clearly downgrades both the DPC and the National Economic Council, which have traditionally split White House action on health issues. The question for Mr. Obama is: Who will give him unvarnished, independent counsel on the recommendations of his HHS secretary?

Finally, the Obama team continues discussing how to use its campaign email list. According to press reports, the aim is to "place pressure on key legislators." But that raises problems beyond irritating representatives and senators who will resent the White House for making their lives more difficult. Ethics and election law expert Tom Josefiak of Holtzman Vogel PLLC says the Obama White House should reread the Department of Justice Office of Legal Counsel's opinions about The Anti-Lobbying Act. One in 1988 warned: "We caution against grassroots appeals, even by the President, that involve substantial expenditures of appropriated funds." This suggests putting the email list on White House servers is a problem.

And who will direct and pay the organizers that the transition team may hire to lead these White House lobbying efforts? Former FEC Chairman Michael Toner, now of Bryan Cave LLP, says running a new grass-roots advocacy group out of the White House could create serious election-law difficulties. The FEC has imposed large civil penalties on some advocacy groups for failing to register as political committees and abide by hard-dollar contribution limits. Also, any White House advocacy group runs the risk of being treated as a Democratic National Committee affiliate, triggering shared contribution limits, reporting requirements, and a prohibition on soft-money contributions. Given Mr. Obama's professed support of campaign finance reform, he could ill afford any of these problems.