The federal indictments of two of former Mayor Kirk Caldwell’s top lieutenants are likely to further cripple Caldwell’s gubernatorial hopes this year, but likely will have less effect on the lieutenant governor’s race.

“It’s hard for me to imagine how Kirk Caldwell will still be able to run for governor with this hanging over his campaign,” Colin Moore, director of the University of Hawaii’s Public Policy Center, told the Honolulu Star-Advertiser’s “Spotlight Hawaii” livestream program Wednesday. “These were folks — at least two of them — who were quite close to him. So I think this is going to be a real challenge and it does upset the dynamics of the gubernatorial race for sure.”

Former city Managing Director Roy Amemiya, former Corporation Counsel Donna Leong, who retired from that post in August 2020, and former Honolulu Police Commission chair Max Sword surrendered Wednesday morning to the FBI and are facing federal conspiracy charges for allegedly misusing city money to give a $250,000 payout to then- Honolulu Police Chief Louis Kealoha.

In late 2020, Caldwell left office after two terms with low approval ratings, in part, because of the corruption scandal surrounding Kea­loha — who is now in federal prison along with his estranged wife, former Deputy Prosecutor Katherine Kealoha — and because of ongoing frustrations with the city’s troubled rail project, which Caldwell inherited.

Party primaries are scheduled for Aug. 13, followed by the general election on Nov. 8.

Caldwell’s hopes to become Hawaii’s next governor struggled early, with his campaign raising just $9,760 in campaign contributions in the six months before August.

By comparison, Lt. Gov. Josh Green’s gubernatorial campaign raised $424,212. Updated campaign disclosures are expected later this month for the race that has since been joined by former first lady Vicky Cayetano.

For Caldwell the indictments of Amemiya and Leong, in particular, “hurt him,” political analyst Neal Milner told the Star- Advertiser. “He’s not in the best shape running for governor. People out there are going to assume he’s responsible because it happened on his watch, same as rail. He’s not going to use this to ride a crest of public opinion.”

Although Caldwell has not been accused of any wrongdoing, Milner said, “You can be assured that part of the FBI’s strategy, as you would expect, is to put pressure on the next level up.”

Amemiya is the cousin of Keith Amemiya, who is running in the crowded race for lieutenant governor this year.

Neither Caldwell nor Amemiya immediately responded to Star-Advertiser requests for comment on the potential political fallout of the indictments on their respective races.

During his unsuccessful bid for the nonpartisan office of Honolulu mayor in 2020, Keith Amemiya campaigned as a first-time candidate and stressed to voters that he was a political outsider and independent from his cousin. Amemiya lost to Rick Blangiardi, another first-time candidate and businessman.

Political pundits maintain that an untold number of voters likely associated Keith Amemiya with his cousin and unfairly linked him to their criticisms of the Caldwell administration.

Moore told “Spotlight Hawaii” that Amemiya and former state Sen. Jill Tokuda are the early leaders in the five-person race so far to become lieutenant governor because of their name recognition.

Asked if Keith Amemiya’s familial relationship with Roy Amemiya will hurt him with voters, Moore said, “It probably does. It’s not fair that it does because we’re talking about two different people. But I think in the minds of voters they probably will be connected to some degree. And so I think he’s going to have to do that work to distance himself yet again.”

For Amemiya, Milner said, “I don’t think this is a significant issue … other than reminding people it was his cousin and he had nothing to do with this.”