I have to admit that what first drew me to interviewing the political strategist and tireless Hillary booster Tracy Sefl, now living in Chicago, was her unlikely friendship with Matt Drudge, the founder and chief cook and bottle washer of The Drudge Report. Drudge became famous—or infamous, depending on your political persuasion—in January of 1998 by keeping on the front page of the nation’s newspapers every salacious, shocking detail of Hillary’s husband’s affair with White House intern Monica Lewinsky (including some that weren't so true in the end).

Fast forward to 2008 when Sefl, then working for Mrs. Clinton in her presidential primary race against Barack Obama, acted as Hillary’s liaison to Drudge. At that time, the site drew some 20 million hits per day.

Sefl was born in Hinsdale, Illinois, and grew up in Cedar Rapids, Iowa. She now lives in Old Town with her husband, a psychologist who teaches at Northwestern Medical School. The 43-year-old “Democratic communications strategist” tells me over a meeting at a pastry shop on Wells Street—and in subsequent email exchanges–that these days she counsels campaigns, candidates, executives, and authors. “My solo consultancy doesn't have a name, quite purposely so. I do often collaborate with other consultants, including Republicans—within reason—when the work warrants it.”

Most noteworthy on her resume, especially should Hillary become president, Sefl was a senior adviser to the now-defunct superPAC Ready for Hillary. The group dissolved in late April after Hillary announced she was running. Sefl now divides her time between Chicago and DC.

Back to the mysterious Drudge, whose politics lean way right, but who, Sefl told me, seemed “fascinated” by Hillary. Sefl ran with that, and, in 2008, she was routinely dubbed as Hillary’s go-between. New York Times reporter Jim Rutenberg described Sefl as so skilled at this role that her “fingerprints are usually impossible to spot.” (When asked what the campaign thought of Drudge, Sefl says, “The mystery of Matt in 2008 is that he was part antagonist and part fan.”)

In October 2007, Rutenberg reported—and Sefl does not deny—that as then-Senator Obama “prepared to give a major speech on Iraq one morning a few weeks ago, a flashing red-siren alert went up on the Drudge Report Web site. It read, 'Queen of the Quarter: Hillary Crushes Obama in Surprise Fund-Raising Surge’." Later on in that piece, "Mrs. Clinton's aides declined to discuss how the Drudge Report got access to her latest fund-raising figures nearly 20 minutes before the official announcement went to supporters. But it was a prime example of a development that has surprised much of the political world: Mrs. Clinton is learning to play nice with the Drudge Report and the powerful … and conservative-leaning man behind it.”

Sefl first met Drudge, she told me, at a Washington party in 2004 when she was “a war room staffer” doing rapid response and opposition research on both George W. Bush and Dick Cheney. “I had so much to work with,” she quipped. She had earlier explained to me that she and Drudge “developed a relationship that was beneficial to us both. He’s a businessman and he knows how to be a businessman.” Drudge was quoted as saying on his now defunct radio show, "I need Hillary Clinton. You don't get it. I need to be part of her world. That's my bank. Like Leo DiCaprio has the environment and Al Gore has the environment and Jimmy Carter has anti-Americanism. I have Hillary."

Sefl was still nurturing the Drudge tie as late as June 7, 2008, the day of Hillary’s concession speech at the National Building Museum in D.C. Sefl invited Drudge to meet her at the event. “He had checked in to see how I was doing. He was in town. We just decided to go to the event together. We tried to hang out in the back.”

(Drudge was not by any means always kind to Hillary during the 2008 battle. As Obama took off, Drudge reported rumors of a Hillary lesbian affair with an aide; Drudge also ran what Politico called “unflattering but attention-grabbing photos of Clinton looking tired and haggard,” and a string of “campaign turmoil” stories.)

Sefl, who graduated from Cornell College, spent more than a decade working for Bill Clinton’s best friend and supporter Terry McAuliffe, who is now governor of Virginia. The relationship started when she went to work for the DNC in 2002 while McAuliffe was chairman. She stuck with McAuliffe, “helping” with his 2007 book What A Party: My Life Among Democrats: Presidents, Candidates, Donors, Activists, Alligators, and Other Wild Animals. She then signed on as his press aide in 2007-08 when McAuliffe chaired Hillary's primary campaign, and also assisted with the launch of his electric car company, the subject later of much controversy. Finally, Sefl helped with McAuliffe’s 2009 bid to become Virginia’s governor. He was unsuccessful that time, but won the next time around. “He wisely chose to eschew national media,” Sefl told me, “so my role was primarily to cheer him on.”

​Her role this time around in helping Hillary for what is presumably her last run for the White House was a hugely important one. Ready for Hillary has provided the former First Lady, senator, and Secretary of State with a four-million-name email list that Politico reporter Annie Karni described as “a data gold mine that will immediately bolster the Democratic front-runner's fundraising and organizing efforts.” If not for that, Karni noted, Hillary would be stuck with “an outdated supporter list from 2008” that, the New York Times’ Amy Chozick and Patrick Healy reported, “had only about 100,000 active email accounts.”

Sefl says proudly that Ready for Hillary, which started with two volunteers in “someone’s living room,” had, at its height, 35,000 volunteers, 29 staffers, and raised more $15 million from 135,000 donors.

Starting in June, 2014, Sefl served as a “surrogate”—her job was to talk to the media — during Hillary’s tour to promote Hard Choices, her memoir of her years as Secretary of State. “We purchased an RV [a 2011 Winnebago, made in Iowa, she notes proudly], wrapped the back of the bus in the iconic photo of Hillary wearing sunglasses on her Blackberry. Across the photo, we added the text, `DON’T TEXT AND DRIVE.’"

Last May, when Hillary came to Chicago to fundraise, Sefl attended the event at J.B. and M.K. Pritzker's house. "She wowed the crowd that night, including a gentleman next to me who said she would be the first Democratic presidential candidate he'd ever vote for. She took time with everyone, which is always an amazing feat to witness, and I was happy to have a chance to talk with her then, as well.”

I asked Sefl why Hillary, who officially launched via video to intense media hoopla in April, needed a re-launch in June. “She wanted to build upon her digital launch with a traditional rally, complete with a beautiful setting and an excited crowd. ….Her speech on [New York’s] Roosevelt Island reflected some topics that emerged from her first weeks of campaigning. She wanted to have those first weeks to hear from people across the country, and give thought to addressing their concerns.”

Sefl, who can spin with the best of them, responded to my question about how Hillary did in her much-hyped nationally televised sit-down of this campaign last Tuesday in Iowa City, with CNN’s senior political correspondent Brianna Keilar. The interview was generally panned, though there were some highlights, Sefl says, such as when she discussed the recent effort to have a woman on currency.

“I want a woman on a bill,” Hillary told Keilar, but on her own bill. Clinton bashed Treasury Secretary Jack Lew’s plan to have a woman share the $10 bill with the nation’s first treasury secretary, Alexander Hamilton. She called it “second class.” 

“I really loved her answer [to that],” Sefl wrote me by email. “I would advise her to answer more questions that way.”

To my question about Hillary’s handlers, who used a rope-line to corral the press during a Fourth of July parade in New Hampshire, Sefl answered, “I’m on Team No More Ropes.”

To my question of whether Hillary should take on Bernie Sanders—she rarely utters the name of the man who is gaining on her in the first caucus state, Iowa, and the first primary state, New Hampshire—Sefl acknowledges the record-breaking crowd of 10,000 Sanders attracted in Madison, and answers, “I would hope all the other campaigns are looking analytically at all of the reasons driving that.” Presumably she means that Hillary’s campaign should take a look as well.

"Who will be her vice president?” I ask. “That will be a parlor game for a very long time. I’m exhausted just thinking about it,” she says.

Could the VP pick be another woman, say Minnesota Senator Amy Klobuchar? “I think that would be great. …I would love to see two women, but I don’t think it’ll happen this time.”

She adds that she doesn’t think it will be Rahm Emanuel—she describes herself as “an admirer,” having come to know him when he chaired the DCCC while she was at the DNC. “Given that he was just reelected. I hope he remains my mayor.” She even wrote a Wall Street Journal piece that ran the day after the election in which she praised Emanuel for raising the minimum wage, working toward universal full-day kindergarten, waiving community college tuition, opening city jobs to DREAMERS, and more.

She has no inside scoop on the possibility that Joe Biden might challenge Hillary in the primary, but says that Joe and Hillary are “pals;” they were colleagues in the Senate, they served in the Obama administration, and seem to be “genuine friends.”

And what should the campaign do about Bill? “I have so much admiration for what he can do,” she answers. “I remember watching him do an event for Rahm last summer. He was marvelous. I believe he’ll respect the campaign strategy and where there’s a place for him, you bet he’ll be there.”

We also talked about the difficulty women face in being dressed and groomed for the day-to-day grind of campaigning. “Men get uniforms—dark suit, white shirt, striped tie. Women get costumes. I couldn’t imagine every time I stepped out of my front door having to be in a constructed state of photo perfection.”

In our first conversation, Sefl told me that she is still decompressing from her DC life and getting accustomed to the fact that Chicagoans think about things other than the 2016 presidential race. “The presidential election is not what dominates people's conversations here. I have to confess that was extremely disconcerting for me at first, but now I'm learning to enjoy it.”

She skipped the re-launch because “our neighbors lobbied us that the Old Town Art Fair was worth staying in town for, so I chose to DVR the Roosevelt Island event instead. It turns out my neighbors were entirely right.”

As for the wide assortment of scandals surrounding Hillary: “Normal people don’t know or care,” Sefl says. “They will start to pay attention when it’s time to pay attention. Normal people are not paying attention now.”

I asked Sefl—she told me, “with apologies,” that she can’t remember the last time she was on Matt Drudge’s web site—when was the last time she saw the famously elusive Drudge. “We had a lovely lunch together in Miami a few years ago. I hope these days he's traveling the world and having a great time. His site isn't the same now for a lot of reasons, but he certainly built his empire.”