So, no, I don’t think anyone can have such a clear, planned path. You have to make decisions as you go as to where you think you can make the greatest difference.”

Van Hollen and his wife, Katherine, pictured at the Kensington train station near their home, met when they were classmates at Harvard University’s John F. Kennedy School of Government. Photo by Liz Lynch.

Van Hollen says he was trying to make such a difference in 1994, when he decided to mount a primary challenge to Sher, the state senator who had helped launch Van Hollen’s political career just four years earlier. It remains one of the more controversial chapters of Van Hollen’s political ascent. “While we agreed on the issue of choice, we had very big differences on other issues that were of importance to working families,” Van Hollen says, pointing in particular to Sher’s opposition to legislation at the time that mandated unpaid family leave. “There were people in the consumer protection area, people in the environmental movement and others who were looking at [her] record, and we all agreed we needed somebody who was more progressive.”

Some, however, saw it as a lack of loyalty and, perhaps, a demonstration of raw ambition on Van Hollen’s part. “I told him that he had been selected as essentially the fourth person on that [1990] ticket by Patty [Sher], and that he had some obligation to be loyal to the ticket,” says then-Del. Leon Billings. “Let me just say that we had a series of unpleasant exchanges.” Sher, who died in 2001, was quoted at the time as saying that Van Hollen’s challenge made her feel “like one of my sons had kicked me in the mouth with a boot.”

Billings and Van Hollen later became good friends. “[Chris] worked extraordinarily hard after that Senate election to heal the bruises,” Billings says. “I’m sure it never healed with Patty or Bill [Sher’s husband, a former Montgomery County Council member], but I know it healed with other members of the delegation who were not terribly happy with Chris’ initial decision.”

It was the first big risk of Van Hollen’s political career. By most accounts, Van Hollen ran a virtually flawless primary campaign, fueled by support from the grassroots progressive groups that would also be key in his run for Congress eight years later. Toward the end of the campaign, Sher damaged herself with a comment that was considered racially insensitive. On primary day, it was a 75-25 percent blowout for Van Hollen, who easily won the general election to advance to the state Senate.


If Van Hollen was on an inside track to move up within the congressional leadership almost from the day he arrived on Capitol Hill, he found himself in a very different position at the beginning of his tenure in Annapolis. “I think Chris, for his years in the House [of Delegates], was sort of an outsider,” says former Del. John Hurson, who shared representation of District 18 with Van Hollen. “And when he got to the Senate, he was still sort of an outsider.”

Van Hollen campaigned as an outsider when he challenged Sher, who had been close to the Senate leadership. Initially, his election was hardly welcomed by Miller, the powerful Senate president. But he and Van Hollen quickly mended fences, and Miller later appointed him to an influential post as vice chairman of the Budget and Taxation Committee. Says Hurson: “I think Mike Miller ultimately realized how smart and how capable Chris was, and wanted to capture and use it.”

Three years after being re-elected without opposition in 1998, Van Hollen was preparing to give up his safe seat in another gamble. Redistricting had made the 8th District congressional seat held for 16 years by Republican Connie Morella a leading target for national Democrats. But with a 75 percent favorability rating and a voting record that had put distance between herself and national Republicans, Morella’s ouster was hardly assured.


To get the chance to take on Morella, Van Hollen first needed to find a way to defeat then-Del. Mark Shriver of Potomac, a nephew of former President John F. Kennedy who brought the family’s money and aura to the contest. At the outset of the 2002 election cycle, Shriver’s nomination in the Democratic primary was widely regarded as inevitable.

“That was a big step into the unknown,” Van Hollen says. “It was clear the odds were against me, at least in most people’s perception. But look, I had worked with these coalitions of people who were interested in bringing about change in the state legislature. Mark and I had very similar voting records. The difference was actually working with these grassroots coalitions to move these issues from ideas to law. So I had some faith that these grassroots groups would get behind the effort—and that’s exactly what happened.”

At the outset of the campaign, “Chris was quite provincial in many ways,” says former Montgomery County Planning Board Chairman Gus Bauman, who got behind the Van Hollen effort. “…It was amazing who he didn’t know. But Chris was out there, going to all kinds of people saying, ‘I need your help,’ because he knew who he didn’t know. Mark just assumed that, ‘Of course I’ve got their support.’ ”


Years later, a widespread view of the contest is that Shriver was overconfident and Van Hollen outhustled him, that Shriver was perceived as the show horse and Van Hollen as the workhorse, particularly among people in the local Democratic precinct organization. (Shriver declined two requests to be interviewed for this story.) But several who played roles in the 2002 election say this hindsight perspective underplays the potency of the Shriver campaign, whose consultants included David Axelrod, a key player in Barack Obama’s campaign for the White House.

“It was one of the toughest campaigns I’ve ever seen,” says Miller, who endorsed Van Hollen that year. “This became a family event for the Kennedys, and people who weren’t with Mark were persona non grata. So people had to make some tough choices.”

Van Hollen announced his candidacy for Congress in March 2001, 18 months before the primary. For more than a year, it was largely a volunteer effort. Katherine took a leave of absence from her job to oversee the campaign’s direct mail operation, and Van Hollen’s sister Caroline was in charge of the campaign phone bank. Anna Van Hollen, then in sixth grade, formed “Kids for Chris,” as her two younger brothers marched in parades and helped adults work the polling places. (In the current Senate race, Katherine has been working with the campaign on a “Women for Van Hollen” effort, and Anna often flies in from California on weekends to join her brothers in helping out.)


Van Hollen still trailed in the polls in late spring of 2002, when he brought in seasoned consultant Tom O’Donnell, a former political director of the DCCC, the entity that Van Hollen would later chair. Initially, O’Donnell didn’t want to get involved. “I said, ‘I’m not really interested. I know a lot of the Kennedys. They’re friends,’ ” he recalls.

O’Donnell eventually relented and agreed to meet with Van Hollen. “In my prior career [at the DCCC], I had recruited candidates to run for the House,” O’Donnell says. “So I had a pretty good sense of the type of people you recruit. After spending an hour with [Van Hollen], I said to myself, ‘This guy is as good as anyone I’ve ever seen run for Congress.’ ”

A third candidate in the race saw a sharpening of Van Hollen’s message after O’Donnell’s arrival. “In the closing weeks, Chris essentially began to present himself as ‘the only one who has worked for you in Annapolis and in Washington,’ ”
recalls Ira Shapiro, a former congressional aide and trade negotiator. “Until then, he hadn’t emphasized his work for Mac Mathias and on the Senate Foreign Relations Committee staff. But he made it a major campaign theme. …It was very credible, particularly in the aftermath of 9/11.”


On primary day, Van Hollen squeezed out a 44-41 percent win over Shriver, and, with just two months to go until the general election, faced Morella, who was running the first attack ads of her career. Van Hollen came under pressure from supporters to respond in kind, but resisted the advice in view of Morella’s high favorability ratings. “Chris had the discipline not to get into it with her,” O’Donnell says. “You basically had to run against the Republican agenda, so the whole thing became: ‘Did you or did you not support the Republican agenda?’ not ‘Did you or did you not support Connie Morella?’ ”

That strategy, coupled with a redrawing of the district that had added a slice of heavily Democratic  districts in Prince George’s County, yielded a 52-47 percent general election victory for Van Hollen, making him one of just two Democrats to oust sitting House Republicans nationwide in 2002.

“Chris has an exquisite sense of timing and opportunity, and that has served him very well,” says old friend and current colleague Gerry Connolly. “Even when conventional wisdom told him not to, his instincts were better, his timing was superior.”


It is clear that Van Hollen has long eyed a Senate seat. In 2005, a little more than two years after Van Hollen first won election to Congress, veteran Sen. Paul Sarbanes announced that he planned to retire, and Van Hollen spent the better part of four months exploring a Senate run.

He ultimately decided not to run, a rare instance of opting against an electoral gamble, as much of the state’s Democratic establishment had coalesced around now-Sen. Ben Cardin. Publicly, Van Hollen cited family—his children were still young—and the fact that he been through a grueling 19-month campaign for the House.

In 2010, even while serving as chairman of the DCCC, Van Hollen pointedly declined to rule out a Senate run if incumbent Barbara Mikulski decided to retire. Last March, when Mikulski said she would not seek re-election, it took Van Hollen just days to announce that he would run for the Senate, despite efforts by House Minority Leader Nancy Pelosi, with whom Van Hollen has close ties, to convince him to stay where he was.


According to numerous sources, Van Hollen enjoys a far closer relationship with Pelosi than with Hoyer—even though the two Marylanders go out of their way to publicly praise each other. In fact, when Mikulski announced her plans to retire, Van Hollen was participating in discussions—first reported by The New York Times—that some interpreted as Van Hollen contemplating a challenge to a Hoyer bid to replace Pelosi as minority leader if she decided to retire. Both men have since sought to deny that the prospect of such a collision ever existed. “Chris has indicated to me that was never his intent,” Hoyer says.

Says Van Hollen: “This was a group of members who were trying to figure out ‘What would the future of the House be in the event that leader Pelosi would decide not to run for re-election, and people like Steny and the current leadership were to decide to [retire]?’ ”

Behind this under-the-dome jockeying is the fact that Pelosi and Hoyer are both in their mid-70s, and in recent years, as Hoyer puts it, “Chris was almost always in the group of five or six people” mentioned as a future House Democratic leader. But that clearly begs the question of whether the Democrats will be in a position anytime soon to recapture a majority and enable whoever is leader to become House speaker. Few see it happening until at least the next redistricting, which is six years away. By then, Van Hollen would be approaching his mid-60s.


At the end of a long breakfast conversation, Van Hollen is asked if he would have considered staying in the House if he thought there was the prospect of a Democratic majority in the foreseeable future.

Without answering directly, he replies, “I think the Senate is a place where I have a larger opportunity to make a difference. In addition to making a difference for the entire state, I think it is a place where there are more opportunities to advance a lot of the issues I’ve been working on.”

He adds, “Look, I’m not under any illusion that the Senate is a place of great productivity these days. But I only have to ask you to look at what is happening in the House right now to see that the place is, unfortunately, dysfunctional.” He is speaking on an early October day as, several blocks away, House Republicans are struggling to find someone willing to become speaker of their fractious caucus—a process that ultimately will culminate with the selection of Paul Ryan.


Says Van Hollen, “I think I have done what I can in the House, both in terms of advancing a positive agenda and stopping an agenda that I think is dangerous to the country. So it was time to try to make a difference somewhere else.”

Louis Peck ( has covered politics extensively at the local, state and national levels for four decades.