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Her campaign failed to line up key supporters in New York, from party officials to members of Congress to activists. One planned dinner for New York lawmakers at her Washington home was canceled. Some New York donors said they wrote her a check out of obligation but declined to host fund-raisers for her. Charlie King, a Democratic National Committee member from New York who is unaligned in the 2020 race, said he never heard from Ms. Gillibrand or anyone on her team.

“I heard from several other campaigns,” Mr. King said. “Multiple times.”

Money problems outweigh the bright spots

Ms. Gillibrand’s lack of small donor support — the lifeblood of Democratic fund-raising — was evident from the start. Through June, she had topped 2,500 donations in a day only once; Senator Elizabeth Warren, in contrast, had more than 100 such days.

In May, Ms. Gillibrand’s campaign began to sever ties with Anne Lewis Strategies, the political firm where she had directed $5.6 million in 2017 and 2018, in part, to build a digital supporter list. Few of those people became 2020 donors.

A few months into her bid Ms. Gillibrand was hemorrhaging money. In the second quarter she spent nearly $2 million more than she raised — by far the worst ratio of any candidate who was not self-funding their run.

Rival campaigns took note. Privately, some began discussing how soon would be too soon to attempt to poach some of the talent that Ms. Gillibrand had assembled in her Troy, N.Y., headquarters.

Ms. Gillibrand had some bright spots. She sipped whiskey with voters, dressed up with drag queens in Des Moines, took spin classes everywhere and arm-wrestled with an Iowa college student. Her team quickly packaged these vignettes into videos posted online.