The entrance of a Trump fundraiser held in August at the mansion of car dealer Ernie Boch Jr. (Photo by John Tlumacki/The Boston Globe via Getty Images)

In our post-election series on #Keeping Democracy Alive, we’ve been soliciting essays and opinions of some of the people on the front lines of that battle. As part of that effort, Kathy Kiely sent five questions to Sheila Krumholz, executive director of the Center for Responsive Politics, a nonpartisan nonprofit that provides data on campaign contributions and other information on the relationships between donors and political decision-makers.

Kathy Kiely: In the most recent presidential election, the candidate who raised the most money didn’t win. Why should people still worry about the influence of money on politics?

Sheila Krumholz: In a very real sense, money did win, just not in the way we’re accustomed to measuring it. Trump raised about $248 million — $322 million including all of the allied super PACs like “Great America PAC” and “Rebuilding America Now.” Not exactly chump change, but Clinton raised double that: The campaign alone raised nearly $500 million; $700 million including allied outside groups.

But in presidential general election campaigns, money typically ceases to be the barrier to success for major-party nominees that it can be in the primary or for third-party candidates. Once the general election candidates reach a point of financial viability, it’s less about the money and more about their appeal as candidates and their ability to connect with voters. Neither Trump nor Clinton was hampered by a lack of cash. In fact, both candidates ended the campaign with leftover funds; Clinton with $62 million and Trump with $15 million.

But Trump had been running long before he started to seriously chase campaign cash. And during that time, he earned unprecedented free media. He already was masterful at working the media based on his longstanding reality show, The Apprentice, his beauty pageants (Miss USA, Miss Teen USA, and Miss Universe) and his books (The Art of the Deal, The Art of the Comeback). It was enormously beneficial that he was already a household name in America. On the campaign trail, he was a walking, talking reality show, fomenting political controversy wherever he went and seeming to embrace the notion that there’s no such thing as bad publicity. Arguably he was right. Interviewers often let him hold forth without much, if any, fact-checking or debate. He’s a masterful operator in (some would say “of”) the media and publicity spheres that so often mirrors the political sphere. By that measure he had “spent” $4.3 billion through July.

Kiely: Donald Trump says he wants to “drain the swamp” in Washington. Is there anything about his campaign and transition that makes you hopeful he will? Is there anything about his campaign and transition that gives you doubts?

Krumholz: Whether Donald Trump is likely to be successful in “draining the swamp” depends largely on what you think that means. It may well mean reducing the power and influence of lobbyists — also a goal of Barack Obama in the 2008 presidential campaign. Obama’s first-term efforts were not viewed as being all that successful at “changing the culture in Washington;” maybe they were the wrong efforts, tactically. Whatever the reason, it is extremely difficult to effect that kind of cultural shift, far more than it is to promise it on the campaign trail.

Trump’s supporters like his unorthodox and brash approach — so much so that it may count more than delivering on his promises (his fans took him seriously, but not literally). So will they hold him accountable on “draining the swamp?” The people he has appointed so far are largely affluent elites or political insiders, so it doesn’t seem likely that these will be the folks to finally move Washington away from a system that’s beneficial to or represented by them.

Kiely: What is the single best tool journalists and citizens should be using to better watchdog their elected officials?

Krumholz: Naturally, here at the Center for Responsive Politics we are partial to our own website, Opensecrets.org, which is chock-full of high quality, value-added conflict-of-interest data sets, including: campaign contributions by recipient or by donor industry; spending —…