Taking on the squad: Meet the Democratic investment banker challenging Alexandria Ocasio-Cortez

NEW YORK — Marty Dolan has an unmistakable finance-dad-on-a-Saturday vibe.

Dressed in a grey windbreaker and spikeless golf shoes, with perched Ray-Ban sunglasses pushing up against his thick silver mane, Dolan cut an unlikely figure as he knocked on several doors at Astoria Houses, a public housing development in Queens, on a Tuesday in May.

The words emblazoned on his windbreaker offered a clue: “Marty Dolan for Congress NY-14”

The 66-year-old investment banker is mounting a primary challenge against Democratic superstar Rep. Alexandria Ocasio-Cortez from New York's 14th district, which includes parts of the Bronx and Queens.

'Not a radical.' Dolan pitches more moderate brand of progressive politics

Dolan describes himself as a progressive ? but not a “radical.”

That’s a term he reserves for Ocasio-Cortez, the most popular member of "The Squad” which is made up of the most liberal politicians in Congress.

Dolan is betting that New Yorkers sick of her stance on Democratic policies have become a flashpoint within the party, will vote for him in the June 25 election. He says New York's taxpayers are burdened and see their quality of life ruined.

Running against Ocasio-Cortez, famously known as A.O.C, is an uphill battle for the political newbie who announced his candidacy against the three-term incumbent in March.

But if Dolan is an unknown political quantity, so was Ocasio-Cortez when she ran first ran for her seat in 2018. The former bartender who worked on Sen. Bernie Sanders’ presidential campaign stunned the political establishment by defeating Joe Crowley, a 10-term incumbent in a major midterm elections primary upset.

In 2019, at age 29, she became the youngest woman ever to serve in the U.S. Congress.

Dolan charges Ocasio-Cortez, 34, has been derelict in her duty towards her constituents in the Bronx and Queens neighborhoods that make up her district. He especially blames her championing policies that have seen New York City dealing with an undocumented migrant crisis and for her support of bail reform which he says have made quality of life worse for its residents.

“The increase in undocumented immigrants arriving in New York are competing for resources with her (Ocasio-Cortez’s) constituents,” says Dolan. “The consequences of A.O.C dumbly encouraging global migration with the prize being a 2,200 mile walk from Ecuador to Texas is 25,000 to 50,000 civilian casualties along the Central American trail to El Paso.”

New York City and the migrant crisis

New York City should no longer be a “sanctuary city” – a policy which discourages local law enforcement from reporting the immigration status of individuals unless it involves investigation of a serious crime, says Dolan. The city also has a “right to shelter’ law which guarantees a bed to guarantee a bed to anyone who sought one the same day.

More than 200,000 asylum seekers have come through the city's intake system since the migrant crisis began in the spring of 2022, according to New York City officials. Mayor Eric Adams, who said last year "the issue will destroy New York City" says so far, the city has spent $4.6 billion on the crisis.

Last November, the mayors of Chicago, Denver, Houston, Los Angeles and New York wrote a joint letter to President Joe Biden about getting federal help in managing the surge of migrants.

"We're going to do our job," Adams said in February. "But we should be asking the national government: Why is this happening to Chicago, New York, Los Angeles, Houston, Washington?"

Polling also shows how the Democrats' views on the migrant crisis has changed over the past couple of years.

In 2022, 42% of Democrats thought the government was doing a good job on dealing with large number of migrants at the border. By 2024, that only about a quarter of Democrats thought that, according to a poll by Pew Research.

"We need to freeze the border and send that message to the world to stop the death and casualties along the way," says Dolan. "The Republicans are right on this issue.  But that doesn’t make me a Republican.  No party is right on every issue."

On his campaign website, Dolan who has served as managing director at banks including Lehman Brothers, Morgan Stanley and JPMorgan Chase, puts the city’s current plight thus: “Bail reform a disaster, the National Guard in the subway, toothpaste locked up in drugstores but criminals running free.

Dolan is a proponent of having uniform policies across federal, state, county and city lines on everything from taxes to immigration—as determined by the federal government. He calls it “Hamilton Plan 2.0” in honor of Alexander Hamilton, the nation’s first treasury secretary.

“It makes no sense to have competing national, state, county, and city policies,” he says. “Cities are agencies not sovereign entities.  This is where all the confusion and subsequent mayhem comes from.”

A.O.C primary: Not debating her primary challenger 'An insult to voters'

Dolan says Ocasio-Cortez, who hasn’t faced a primary challenge since 2020, has not responded to his campaign's invitation to debate him.

In an interview with the Bronx Times, Ocasio-Cortez responded saying: “I don’t see dignifying him with one.”

Ironically, in 2018, when the congresswoman first ran for her seat, her opponent, then-incumbent Crowley, was heavily criticized for sending a staffer in his place.

When USA TODAY asked Ocasio-Cortez’s office about her refusal to debate Dolan, her office responded saying they would not be commenting for the story.

“It's an insult to the voters,” said Dolan. “She said it would be beneath her dignity to debate with us. I think she knows that I would ask questions that she wouldn't have answers for.”

A son of an Argentinian immigrant of Irish descent and an American mother, Dolan grew up with eight siblings in Irvington, an affluent suburb in Westchester County. His father was a physician – who arrived on a work visa-- and his mother a nurse.

“My mom and dad focused on education,” he said. “We all worked our way through college.”

Having spent his early years in a cramped two-bedroom house with nine people ?7 kids and both parents ? Dolan is passionate about renovating old homes.

"I went from living in the smallest home to owning the home with the highest taxes in town," he says. He's renovated a home in London, and in 2020, completed a project on a historic home in Irvington that took more than a decade.

"It went from being, you know, completely an abandoned house into the largest taxpayer in the school district," he says.

Dolan, who has a background in finance, says NYC has 'financial cancer'

Dolan, who is thrice divorced and a father of three grown children, says he was looking for the next big challenge.

As a longtime New Yorker (from 2000 to 2020 he lived in both Manhattan and Westchester County), he says he was troubled by how the radical agenda was pushing the city to the brink.

"The taxes are through the roof and they want to raise it more," he says. "They know nothing about taxes and they know nothing about business. I know and understand these things."

Dolan says New York City has "financial cancer," and his work as a banker in reinsurance and risk uniquely qualifies him to tackle the city's financial problems.

His opponent has "grievously injured" New York City's reputation as place to do business as a result of her opposition to the Amazon HQ deal, he says.

"It's become reputationally uncompetitive," he says. "Businesses would rather go to other states."

When Dolan decided to challenge ‘radical’ politicians in New York, his first mark was Rep. Jamaal Bowman (NY-16). But when Westchester County Executive George Latimer, a moderate Democrat, decided to primary Bowman, Dolan shifted his focus to Ocasio-Cortez.

Dolan, who has an MBA from Harvard Business School and has worked at several big banks, both in the US and Europe, is currently renting an apartment each in the Bronx and Queens to better reach voters, he says.

Coincidentally, Ocasio-Cortez also grew up in Westchester County, in a wooded suburb called Yorktown Heights, just 17 miles north of Irvington. She was born in the Bronx and moved to the northern suburb at age 5.

New York's 16th Congressional District: Two candidates with Westchester County connections duke it out

New York's 14th congressional district is one of the nation’s most diverse, with a majority Hispanic/Latino population (47.5%), according to the U.S. Census. More than 60% of the households speak a language other than English at home and 20% of the constituents lives in poverty. Ocasio-Cortez has Puerto Rican roots.

The winner of the primary is almost assured to win the general in this heavily Democratic district, where historically, Democrats have won more than 65% of the vote.

But Dolan is going up against a well-known candidate flush with cash.

As of March 31, Dolan had raised a little more than $250,000, out of which $222,500 was loaned by the candidate to himself, according to FEC filings. He raised about $28,000 in contribution and had a little more than $26,000in cash on hand.

During the same time period, Ocasio-Cortez had raised more than $1.6 million in contributions (with a total of $6.8 million in the election cycle) and had more than $6 million cash on hand.

Eliot Engel, who served in Congress for 32 years, and was defeated in 2021 by Bowman, continues to live in the Bronx.

He says Dolan’s moderate policies are what New York needs. He believes Ocasio-Cortez’s politics, such as voting against the Bipartisan Infrastructure Bill and scuttling the effort to build Amazon headquarters in Queens, shows she’s more interested in “political aggrandizement” than helping her constituents.

“It would have created so many jobs, and she voted against it, and that was very irresponsible,” he said. “She’s interested in being a big shot and running around the country than she is in bringing jobs to her community.”

Engel says the congresswoman’s focus has been on gaining national attention to run for higher office.

“People want to have a better standard of living and they want somebody whose main reason for running for office is to produce for their community," he said. "Not to just get up in front of a soap box and audition for national office.”

Many of Ocasio-Cortez's recent town halls with constituents have been marked with chaotic disruptions and hecklers.

At one town hall, a man shouted: “American citizens before migrants.”

In May, as Dolan went around knocking on doors at the Queens housing project, most people didn't answer. At many apartments, which remained closed, dogs barked loudly. When, occasionally, a resident answered, they seemed unaware of the June 25 primary. For all the name recognition and social media followers that Ocasio-Cortez has, people in this apartment building didn't seem to know who she was.

"Campaigning is not easy," Dolan said.

Asked why he didn't pick another old house to renovate as the next challenge, he said: "Renovate? Well, that's exactly what I'm doing. I'm renovating the House of Representatives."

Swapna Venugopal Ramaswamy is a White House correspondent for USA TODAY. You can follow her on X, formerly Twitter, @SwapnaVenugopal

This article originally appeared on USA TODAY: AOC primary: Who is the NY Rep's election challenger Marty Dolan?