Collectively, the staff had little expertise with the sort of high-stakes analysis she wanted for the state’s No. 2 official, and few connections to New York Metropolis’s political insiders who may have helped them type by warning indicators. Asking Mr. Cuomo’s seasoned senior aides for assist was out of the query as a result of Ms. Hochul’s staff largely distrusted them.

Nearly instantly, Ms. Hochul, a white reasonable Democrat from Buffalo, indicated to advisers that she was in search of a working mate from New York Metropolis, ideally a youthful Black or Latino Democrat who may improve her credibility in communities that hardly knew her.

Her staff ended up critically vetting two candidates, each thought of rising stars within the State Senate: Mr. Benjamin, a former businessman, and Jamaal Bailey, who led the Bronx Democratic Get together committee.

Mr. Benjamin had a leg up. An Ivy League graduate who had spent a lot of his profession working in banking and reasonably priced housing improvement, he had risen shortly in Albany since his election in 2017. His heat relationship with Ms. Hochul, who had spent seven icy years as Mr. Cuomo’s No. 2, labored in his favor, she informed associates. A number of outstanding New York Metropolis leaders — together with Kathryn Wylde of the Partnership for New York Metropolis and the Rev. Al Sharpton — privately praised Mr. Benjamin to Ms. Hochul.

Nonetheless, some political leaders, together with Keith L.T. Wright, the chairman of the Democratic Get together in Manhattan, quietly raised considerations with Ms. Hochul about Mr. Benjamin’s political standing. He had finished fourth in his race for comptroller, failing to even carry his personal State Senate district in Harlem. Others questioned the knowledge of choosing a working mate from Manhattan, given the shift of Black energy towards Brooklyn and different boroughs.

Mr. Benjamin additionally had baggage that was well-known amongst New York Metropolis Democrats.

A property he owned in Windfall, R.I., had been foreclosed upon. Data present that he had did not pay taxes in New York and Rhode Island a couple of decade in the past, resulting in tax liens (since repaid). He had appeared as a love interest of a major character on the Oprah Winfrey Community’s “Love within the Metropolis” actuality present, however was accused of being a thief after the connection ended.

And as early as the primary months of 2021, stories have been circulating about marketing campaign finance irregularities associated to Mr. Benjamin’s comptroller marketing campaign and a marriage celebration.