In a town that typically sorts people as insiders or outsiders, Pelosi is an unusual mixture of both. Most speakers historically excelled at the insider game: building up favors and relationships with colleagues, while plotting ways to move up the party ranks. Once established as speaker, they had a base to expand national contacts and outreach. By contrast, Pelosi – a lifelong Democratic fundraiser – began her freshman year in the House with her own network of national donors. Over time, she tapped these contacts to move votes on the floor.
The key to Pelosi's success is her drive and mastery of detail – the working knowledge she has of who her members are, what their districts need, and who on the outside can be mobilized to affect their votes. In short, she knows the critical "back door" to members.
It's a skill set that no previous speaker had to the same extent, because none spent the time that she has working contacts on the outside. Since entering leadership in 2002, Pelosi has raised $162 million for Democratic candidates. It's an unthinkable sum for previous speakers and shows the increasing importance of vast war chests to win and hold majorities in bitterly partisan times. With a few calls or a well-timed fundraiser, she can sweeten a tough vote or pressure a member considering an unhelpful one.
Call it the art of political cover. In an era of pure partisan gridlock, no one is doing it better.
PELOSI LEARNED THE FINE ART of sustaining political support from her earliest years in a leading political family in Baltimore. Her father, Thomas D'Alesandro Jr., was serving in the US House of Representatives when she was born. He was the mayor of Baltimore from when she entered first grade until she went away to Trinity College in Washington, D.C. Her brother, Thomas D'Alesandro III, was mayor of Baltimore from 1967 to 1971.