Caruso’s predicament is a reminder of a bitter truth about politics: Money can get you only so far. It reflects the fact that in a deeply Democratic city, many are apparently unwilling to support a former Republican-turned-Democrat who, despite his insistence that he supports the right to abortion, has donated to anti-abortion candidates in the past.

There’s also the reality that Caruso faces a shifting mood less favorable to his relatively conservative message — and a strong candidate in Bass, a highly regarded congresswoman who almost ended up as President Joe Biden’s vice president.

“The conversation has shifted in ways that are helpful for Bass,” said Jessica Levinson, a Loyola Law School professor and elections expert.

The Caruso campaign insists it’s way too soon for a post mortem.

“It’s a little short-sighted to say ‘Well, he spent $40 million and then came in second,’” said Areen Ibranossian, a senior adviser to the campaign. “Anybody who counts us out is not really looking at the dynamics of the race.”

At the start of the year, Caruso seemed primed for a run at an office he had eyed for years. He had money, powerful connections from his decades as a developer of high-end shopping centers and celebrity friends like Kim Kardashian. He also had an electorate in a sour mood after two years of pandemic that seemed receptive to his message, which centered around fears of rising crime and the increased presence of homeless people around…