Just five years ago, the party saw Carl Heastie become the first Black Assembly Speaker. Representative Joseph Crowley had a shot to be next in line to replace House Speaker Nancy Pelosi given his standing as the fourth highest-ranking Democrat. Bronx State Senator Jeff Klein, who reigned as head of the Independent Democratic Conference, pumped the Bronx full of millions of dollars in member items.

There was also the hope that Bronx Borough President Ruben Diaz Jr., would become a serious contender for mayor, with the party ready to pull all the political levers to make that happen. Meantime, Representative Eliot Engel, Assemblymember Carmen Arroyo, and then-State Senator Ruben Diaz Sr. remained unchallenged. Behind all of them was its newly elected party leader, Assemblymember Marcos Crespo, a centrist Democrat and political street fighter.

Now, in the summer of 2020, Crowley and Klein are long gone, ousted by Alexandria Ocasio-Cortez and Alessandra Biaggi. Engel lost his primary this year to first-time candidate Jamaal Bowman. All three of those were defeated by first-time, progressive Democrats. All three losers were backed by the party.

Diaz Jr. announced earlier this year that he's dropping out of the mayoral race and retiring from politics when his term ends in 2021. A few months later, the elder Diaz announced his retirement after he fell short in the 15th Congressional District primary race, with the win going to Councilmember Ritchie Torres, another Bronx lawmaker who did not receive party backing (the party did not endorse anyone in the 12-person race). The seat opened after its current seat holder, 15-term Representative Jose Serrano, announced he'll retire from politics at the end of the year.

Carmen Arroyo didn't even make it on the ballot for the June primary, giving her rival, Amanda Septimo, a default win for the South Bronx Assembly seat.

And within the party's hierarchy, nine of the 24 newly elected district leaders—charged with choosing a county boss—were not endorsed by the party, providing them greater autonomy.

From this, a new freshman class of politicians has emerged, reformers just starting out and free of party allegiance, knocking the party down a few pegs. The hits could keep on coming next year, as a wave of New York City Council races could reshape the party further, with insurgent Democrats already making it known of their intentions to run.

"They're not at their strength of let's say 20 years ago, but parties have been in a period of flux for some time," said George Arzt, a seasoned political consultant who regularly advises Bronx lawmakers.

Further putting the party at a crossroads is Crespo's resignation from both his party and Assembly post, accepting a high-paying job in the private sector. The next leader will be charged with fixing the perception of an organization that shuts out dissenters and would-be lawmakers, despite stubborn pronouncements by Crespo over the years that it serves a big tent.

Marcos Sierra, a former employee with the Bronx Board of Elections steeped in borough politics, recently regained his post as elected district leader after running against his successor. He said he has witnessed Crespo's heavy-handed leadership of the party.

"There have been families...who have been in control of Bronx politics for a long time. And the people are tired. When you build your house on sand, it doesn't last long. That's what the former iteration of the Bronx Democratic Party was," said Sierra. "And with all of the changes that are going on, it is an opportunity to rebuild our political apparatus in the Bronx so that it properly represents all of the people equitably and the previous leadership didn't do that."

Sierra puts himself in the camp of the nine of the 24 district leaders recently elected and not beholden to a party leader's agenda. They're "independent thinkers," according to Sierra, free to express ideas that would have been unpopular under Crespo.

The next party boss, which district leaders will elect this year, will have to sidestep the political morass that was common during the early 2000s when Assemblymember Jose Rivera ran the party, sparking plenty of infighting that led to his ouster. Sierra hopes the next leader is "open-minded and humble," and "who listens more than they speak; who embraces other political clubs that want to start."

Several names have surfaced as possible replacements for Crespo, including Assembly Members Latoya Joyner, Victor Pichardo, and Karines Reyes. With the Bronx home to more Dominicans these days than Manhattan, there have been steady calls for Pichardo and Reyes, who are Dominican, to vie for the spot. Both have publicly expressed interest.

Anyone who succeeds Crespo will have to deal with the growing number of insurgent Democrats activated by the current political climate, forming groups such as the Bronx Progressives, while also contributing to the growing membership of the Democratic Socialists of America, who've demonstrated an astute ground game that involves volunteers and a formidable social media following. To take one small example, the Bronx Democratic Party has just over 1,400 Twitter followers, it's nothing compared to New York's DSA chapter of 33,000 followers. The Working Families Party, which backed Bowman, has close to 17,000 followers.

"County basically is both bodies and 'bagging,'" said Bob Kappstatter, former editor of the Daily News' Bronx Bureau and a political consultant, referring to the process of volunteers helping to get the word out through mailers, phone banking, and canvassing. "But not so much anymore. With the number of progressives now involved as a major wing in the party, I could also see them forging a takeover at the party convention in September."

Circumventing the party apparatus is slowly becoming the norm for many would-be candidates looking for support. Septimo, the default winner of the primary against Arroyo, is among them.

"There is an entire group of people who are running and they're not asking permission, and are not asking questions about how to do things. They're really charting their own path and they think that the tone of how the party itself functions will be set by the next leader," said Septimo. "And they will really have an opportunity to decide whether they want to be more inclusive and widen the tent to a point where those people who are not asking questions are also welcomed."

Under party rules, a county leader must be chosen between September 17th and October 6th, typically at their next party convention, though Assemblyman Jeffrey Dinowitz, a long-serving legislator, notes the county committee could pick an interim leader before the deadline.

While Dinowitz concedes that "machines" have become widely unpopular with voters, he remains optimistic about the party's future.

"At the end of the day the vacancy in the chairmanship is an opportunity for the Democratic Party to become even more responsive and representative of the people of the Bronx," said Dinowitz, who concedes that the loss of Engel will "make it harder for the Bronx to get things done in the future."

"I know that people are already saying, 'Oh, no, the party's dead. This is dead, that is dead.' I think if we, if we don't look at Twitter, we'll get a more realistic view of what's going on in the world," Dinowitz added.

Arzt, the political consultant, suggested that the reformers would sooner or later become the kinds of leaders they are currently criticize.

"People will take over on the under the banner of being reformers, and and then they'll take over the party and they will suddenly be the establishment, then new reformers will come along," said Artz.