Three years ago, Patrick Kennedy chaired Ward 2 Councilmember Jack Evans’ re-election campaign.

Now, he’s hoping to get his old boss’s job.

Kennedy, a four-term Advisory Neighborhood Commissioner in Foggy Bottom, filed paperwork with the Office of Campaign Finance on Monday to take Evans on in the June 2020 Democratic primary. He is the first candidate to jump into the race for Evans’s seat, a campaign expected to be more competitive than almost any he’s run. Evans is the longest-serving—and currently most embattled—D.C. councilmember.

“Jack has been elected for 30 years for a reason, and largely it’s been a responsiveness to community concerns. I appreciated when he could bring his influence on behalf of the community,” says Kennedy. “The more recent thing has been a bridge too far. This is a very cynical time, and Jack has lost the public’s trust, and it’s just time for a change.”

Kennedy, 27, was referring to the recent revelations of ethical transgressions involving Evans. He’s facing a federal investigation over his ties to a digital sign company on whose behalf he introduced legislation, and was reprimanded by his Council colleagues this month for using his government email to seek employment opportunities with law firms that lobby the Council.

The brewing scandal has prompted calls for his resignation from a leadership post in the D.C. Democratic Party and gave birth to a campaign to recall him from office. It also led the Council to strip Evans of certain responsibilities, including oversight over the city’s sports and events authority and control over certain tax matters that usually fell to him as chairman of the powerful finance committee.

But even against this difficult backdrop, Kennedy realizes that Evans remains a political firmament in Ward 2, so much so that he didn’t even attract a challenger over the last two election cycles—either in the primary or general elections.

Evans did not respond to a request for comment, but in a recent response to efforts to recall him, he reminded residents of his commitment to constituent concerns and said that he had “guided D.C. through financially turbulent times and helped bring the city into its current era of economic prosperity.”

But Kennedy thinks that the city has changed enough in recent years that Evans’s reliance on what he once did may no longer carry as much weight—especially when balanced against the accusations now swirling around him.

“I think it’s just clear that the sensibilities of the District as a whole have moved past him,” says Kennedy. “Evans is a product of a different time, when the city was bankrupt and losing population in droves, and 400 people were being murdered a year. You did have to beg people to move to the District then. I’m not debating what the right thing was to do in 1998, but the city is in a very different place now.”

Kennedy says he doesn’t plan on just criticizing Evans during his campaign, but will instead offer residents a “positive vision.” He says he’ll focus on affordable housing and transportation, pledging to bring to fruition a network of protected bike lanes and dedicated bus lanes. But he also says ethics will be a part of his campaign: he plans on accepting public financing through the city’s new program, and says he wants to do away with outside employment for lawmakers and Constituent Service Funds. (Various councilmembers are already proposing the same.)

“These are the steps you need to take to prove to the public that you take ethics in public office seriously,” he says. “In a different time you could make a nuanced argument for outside employment and CSFs, but it’s time to do away with those provisions altogether.”

But D.C. political watchers say that Kennedy—and whoever else runs against Evans—will still faces tough odds unless the federal or local investigations reveal more misdeeds.

“It’s a real steep climb unless significant shoes drop,” says Chuck Thies, who has run multiple political campaigns in the city. “It’s not easy to take out an incumbent. And whenever Jack launches a re-election campaign, if the Sword of Damocles isn’t hanging over his head, there’s no indication his money will dry up.”

For his 2016 Council run, Evans raised more than $227,000, much of it from the city’s business community. In 2012, he took in more than $370,000.

Incumbents facing ethical and legal controversies have been felled by first-time candidates before: Ward 1 Councilmember Brianne Nadeau defeated longtime incumbent Jim Graham, At-Large Councilmember David Grosso bested Michael Brown, and Mayor Muriel Bowser emerged victorious over Vincent Gray.

But Thies says that Evans hasn’t faced the same degree of public scrutiny that those other incumbents did, and without more fuel to the fire of the current scandal, Evans will still find support from his strong base in Ward 2.

“Jack is a titan. He’s as much a titan in his ward as Marion Barry was in his ward and city. A young upstart ANC commissioner with no experience couldn’t even begin to put a dent in Jack’s armor,” he says.

But Kennedy says he can rely on his work on the Advisory Neighborhood Commission in Foggy Bottom, as well as his time spent studying at George Washington University.

“I’ve worked in the ward a long time. I have a pretty good sense of the different sensibilities in the different parts of the ward,” he says. “I didn’t just wake up yesterday and decided I wanted a Council seat. I’ve been involved for a number of years.”

This story originally appeared at WAMU.