As Mayor Kirk Caldwell prepares to clear out the third-floor corner office at Honolulu Hale after eight tumultuous years, Oahu voters will be asked later in 2020 to choose his successor.

The city’s term-limit law bars Caldwell from running for a third, consecutive term and at least four prominent contenders have announced their plans to run for mayor.

They are former U.S. Rep. Colleen Hanabusa, current Council members Ron Menor and Kymberly Pine, and Honolulu businessman Keith Amemiya. All have announced their candidacies and/or have held fundraisers in preparation for their candidacies.

Others who may enter the fray include former U.S. Rep. Charles Djou and former Mayor Mufi Hannemann, who finished with the highest and second highest favorability ratings respectively in a Star-Advertiser Hawaii Poll in mid-September. They were followed by Hanabusa, Pine, Amemiya, Menor and former state Sen. John Carroll. The mayor’s office is considered a nonpartisan post.

Top among the issue to be debated by the candidates will be the now $9.2 billion East Kapolei-to-Ala Moana rail project, which continues to be a seemingly endless source of new headaches for city officials. While issues continue to arise that appear to jeopardize the project’s chances of meeting its anticipated partial, East Kapolei-to-Aloha Stadium opening date of December, federal investigators have subpoenaed Honolulu Authority for Rapid Transportation records while looking into whether there was mishandling of funds.

To win a nonpartisan city election outright in the First Special Election, held in conjunction with the state’s primary election on Aug. 8, the top-placing candidate must receive more than 50% of the votes cast. If no winner is determined, the two top finishers advance to the Second Special Election, held in conjunction with the state general election Nov. 3.

In addition to rail, how to restore faith in the city prosecutor’s office and the police department will be a topic for debate. Elected Prosecuting Attorney Keith Kaneshiro and Caldwell-appointed Corporation Counsel Donna Leong placed themselves on paid administrative leave over the past year after being informed by federal officials that they are targets for federal prosecutions that most believe are tied to the investigations that led to the prosecution of former Honolulu Police Chief Louis Kea­loha, his wife and ex-Deputy Prosecuting Attorney Katherine Kealoha, and several former Honolulu Police Department officers.

The city also continues to be plagued by an unshakable homeless problem and unyielding affordable housing shortage.

The race for the Honolulu prosecuting attorney’s seat also will be closely watched. The embattled Kaneshiro, whose term expires at the end of 2020, has indicated through an attorney he likely will not seek reelection.

At least five people have voiced interested in replacing Kaneshiro, including former U.S. Attorney and retired Judge Steve Alm, former Deputy Prosecuting Attorney Megan Kau and current Acting Prosecuting Attorney Dwight Nadamoto, Kaneshiro’s hand-picked second-in-command.

U.S. Rep. Tulsi Gabbard’s decision to run for president and forego a reelection means she also will need to be replaced. The 2nd Congressional District includes rural Oahu and the other islands. To date, only state Sen. Kai Kahele has voiced intentions to supplant her.

Term limits mean five of the nine current Honolulu City Council incumbents will be ineligible for reelection — Council Chairman Ikaika Anderson and members Menor, Pine, Ann Kobayashi and Joey Manahan. So a majority of the faces on the Council will be different from the existing roster come Jan. 1, 2021.

In Hawaii County, Prosecutor Mitch Roth announced he is a candidate for mayor, although incumbent Mayor Harry Kim has yet to announce his intentions. Kim is finishing up his first, four-year term this go-around after previously serving two consecutive terms last decade. Roth’s decision to run for mayor means there also will be a wide open race for Hawaii County prosecutor this fall.

In the state Legislature, veteran Sen. Laura Thielen (D, Hawaii Kai-Waimanalo- Kailua) and her mother, longtime state Rep. Cynthia Thielen (R, Kailua-Kaneohe), have both announced they will not seek reelection.

Also worth noting is that Hawaii elections in 2020 will be the first to feature an “all-mail” balloting system. It’s one of four states to go to statewide vote-by-mail in the country. Elections Administrator Scott Nago has already begun to draw heat for his handling of the edict, specifically from critics who feel he has not set up enough voter service center locations.