Jamaal Bowman speaks to reporters after voting at a polling station inside Yonkers Middle/High School, Tuesday, June 23, 2020, in Yonkers, N.Y. Bowman is running against veteran Rep. Eliot Engel in the Democratic primary for New York's 16th Congressional District.
CNN  — 

After a delay for the coronavirus pandemic, New York voters will cast primary ballots on Tuesday.

The attention of the national political world will be on New York’s 16th district, which spans the Bronx and Westchester County and where Democratic Rep. Eliot Engel has easily held his seat since 1988. But Engel faces his most serious primary fight ever – in the form of former principal Jamaal Bowman. Bowman has been endorsed by a who’s who of liberals including Sens. Bernie Sanders and Elizabeth Warren, as well as Rep. Alexandria Ocasio-Cortez, to whom his insurgent bid is often compared.

To handicap the Engel-Bowman race and to break down whether the AOC comparison is fair or dumb, I reached out The New York Times’ Azi Paybarah, an expert in Big Apple politics.

Our conversation, conducted via email and lightly edited for flow, is below.

Cillizza: Why is Eliot Engel in trouble? Is it something specific? Or has he just been around a really long time?

Paybarah: Rep. Engel and his supporters would say it’s an anti-incumbency thing, with a mix of missteps on their end. Yes, he was elected to Congress in 1988 (to underscore how long ago that was, this was the New York Mets lineup that year). Yes he spent weeks outside the district during the coronavirus outbreak. And yes, he did say on a hot mic that “if I didn’t have a primary, I wouldn’t care,” when he and another elected official appeared to be discussing the list of planned speakers at a news conference.

Engel’s critics point to those problems, and say they are not just missteps being taken advantage of in the climate of change, but reflect the incumbent’s drift away from a constituency that has grown more diverse and progressive than the congressman’s record would suggest.

And there’s also Engel’s hawkish foreign policy: he supported the invasion of Iraq a decade ago and more recently, opposed the Iran nuclear deal. (Engel also opposed Trump’s decision in 2018 to withdraw from the deal.)

Cillizza: Jamaal Bowman has never run for office before. Are the comparisons to Alexandria Ocasio-Cortez in 2018 fair or a stretch?

Paybarah: That comparison has been made by a lot of people (I mean, a lot of people) and the basic counters seem to line up (sorry, not done yet: a whole lot of people).

They are/were both first-time candidates of color running to the left of long-tenured Democratic incumbents whose impact on and physical presence within the district draw critical scrutiny.

AOC and Bowman are also decades younger than the people they want(ed) to replace (Bowman is 44, Engel is 73). And they framed their candidacies as part of larger movements to push the Democratic Party in a more progressive direction.

AOC was a bartender, Bowman was an educator, which have become part of the narrative they use to describe their connectedness to people on the ground. It can be hard for people to understand what a person yelling in an empty room (Hi C-SPAN, I love you) is doing to improve life of someone living in The Bronx, or Westchester or anywhere else.

Incumbency sure has a lot of advantages – you literally get paid in money and attention to do the job that your campaign spends even more money to convince people you’ve done well.

But there is a downside too.

If you’re an incumbent when the public thinks the place you work for stinks (like the 1993 Mets), you can go down with the whole team. I mean, how many Mets fans bought tickets just to watch Bobby Bonilla that year? (Which I’m sure doesn’t bother him that much considering his contract.)

Cillizza: The major political figures in New York and national politics – Sanders, AOC, Chuck Schumer, Andrew Cuomo – are on opposite sides of this primary. Why?

Paybarah: Sen. Schumer and Gov. Cuomo are backing Engel and, politically, it feels like it’s the sort of thing they have to do. Both men represent not just the entire state of New York residents, but the entire state of New York Democratic incumbents. What signal would it send to each of those incumbents if the governor and senator didn’t support a fellow lawmaker, some of whose missteps and problems are – how can I put this – not entirely unique to him? Support an insurgency in one corner, and it could boomerang right back at you.

Besides, Schumer and Cuomo are dealmakers, who have been forced to get things done with partners not of their own choosing. To them, the system works when results are delivered, not when slogans are shouted.

Sens. Sanders of Vermont and Warren of Massachusetts are supporting Bowman. The real tell, to me at least, is how many challengers a person supports in their own state, and why?

AOC looks like she is taking the biggest risk. She is supporting Bowman, and looking to oust a neighboring member of her own party.

Cillizza: Speaking of AOC, she went negative on TV in her primary. Is there reason to think she may be in trouble?

Paybarah: Someone once told me there’s two ways to run for re-election: unopposed or scared.

AOC’s main Democratic opponent, Michelle Caruso-Cabrera, has raised money from some very rich supporters. And as one of the most famous politicians in America, there are a lot of people who invoke AOC’s name in order to raise money for their own causes. So it can feel like AOC is running against local challengers as well as opponents far and wide.

Also, this is AOC’s first re-election – and what a weird time to be running. A pandemic. Mail-in votes. Fireworks keeping us up all night. The turnout in a local congressional race is hard to predict so that usually incentivizes the urge to break (or at least tap on) the emergency glass protecting whatever secret weapon campaigns have saved for a last resort.

Cillizza: Finish this sentence: On Wednesday, Engel will be ____________.” Now explain.

Paybarah: “Mustachioed”

I remember New York political reporters joking about how seriously to take Bill Thompson’s run for mayor of New York City because he shaved off his mustache. “For further proof of city Controller William Thompson’s aspirations to a higher office, look no further than the suddenly hairless space beneath his nose,” was how Liz Benjamin good-humoredly described Thompson’s 2007 transformation.

Thompson lost.

Before him, Fernando Ferrer ran for mayor and kept it on. “Ferrer and his mustache won a four-way Democratic primary in 2005, but lost to the facial hair-free Republican Mayor Bloomberg in the general election,” Benjamin wrote.

More recently, Bill de Blasio went from a beard and mustache to Mr. Clean. And he won, twice! (Though, New York magazine gave city residents an opportunity to reimagine de Blasio’s look).

All of that is to say: Sometimes politicians change how they look in order to fit the image they think voters want to see. And sometimes, they don’t.

Engel hasn’t shaved his mustache. And he is generally relying on the strength of his record to win another term in office. This is certainly the most serious challenge he has ever faced. And if that hasn’t gotten him to change the thing under his nose – as it could have done for some other people – I doubt anything will.