Collectively, the team had little experience with the kind of high-stakes evaluation she needed for the state’s No. 2 official, and few connections to New York City’s political insiders who could have helped them sort through warning signs. Asking Mr. Cuomo’s seasoned senior aides for help was out of the question because Ms. Hochul’s team largely distrusted them.

Almost immediately, Ms. Hochul, a white moderate Democrat from Buffalo, indicated to advisers that she was looking for a running mate from New York City, ideally a younger Black or Latino Democrat who could increase her credibility in communities that barely knew her.

Her team ended up seriously vetting two candidates, both considered rising stars in the State Senate: Mr. Benjamin, a former businessman, and Jamaal Bailey, who led the Bronx Democratic Party committee.

Mr. Benjamin had a leg up. An Ivy League graduate who had spent much of his career working in banking and affordable housing development, he had risen quickly in Albany since his election in 2017. His warm relationship with Ms. Hochul, who had spent seven icy years as Mr. Cuomo’s No. 2, worked in his favor, she told associates. Several prominent New York City leaders — including Kathryn Wylde of the Partnership for New York City and the Rev. Al Sharpton — privately praised Mr. Benjamin to Ms. Hochul.

Still, some political leaders, including Keith L.T. Wright, the chairman of the Democratic Party in Manhattan, quietly raised concerns with Ms. Hochul about Mr. Benjamin’s political standing. He had finished fourth in his race for comptroller, failing to even carry his own State Senate district in Harlem. Others questioned the wisdom of picking a running mate from Manhattan, given the shift of Black power toward Brooklyn and other boroughs.

Mr. Benjamin also had baggage that was well known among New York City Democrats.

A property he owned in Providence, R.I., had been foreclosed upon. Records show that he had failed to pay taxes in New York and Rhode Island about a decade ago, leading to tax liens (since repaid). He had appeared as a love interest of a main character on the Oprah Winfrey Network’s “Love in the City” reality show, but was accused of being a thief after the relationship ended.

And as early as the first months of 2021, reports were circulating about campaign finance irregularities related to Mr. Benjamin’s comptroller campaign and a wedding celebration.

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