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Looking back five decades to statehood, Honolulu mayors have marked many of the same political milestones en route to Honolulu Hale. They have been representatives in the House and Senate, they have been executives in the private sector, they have served on the City Council, and as the city’s managing director.

This year, the field of mayoral candidates in Honolulu includes the following candidates:

• The city’s former managing director and acting mayor Kirk Caldwell
• Honolulu’s former Prosecuting Attorney Peter Carlisle
• City Councilman Donovan Dela Cruz
• Civil engineer and professor Panos Prevedouros
• City Councilman Rod Tam

Today we’re offering a checklist for mayoral victory based on Honolulu history. The candidates who can answer “yes” to our questions, may have a competitive edge. We found that each of them can look to the past for reason to believe victory is possible.

CALDWELL: The former managing director and now acting mayor might look to former Mayor Jeremy Harris’ path to city leadership. Like Caldwell, Harris became acting mayor when his boss resigned to run for governor. That was in 1994. Harris was elected mayor in the special election that followed, and held the job for a decade (term limits established during his tenure made him ineligible for re-election in 2004). Just last week, Caldwell noted that the candidate who wins Honolulu’s special mayoral election stands to serve as mayor for 10 years. Caldwell is also a former state representative and has leadership experience in the private sector, like many of those who were elected mayor before Harris.

CARLISLE: The city prosecutor, who resigned Wednesday to run for mayor, likes to tout his relative distance from city politics as a good thing. He says his 14 years as Honolulu’s prosecuting attorney give him a deep understanding of the city, without baggage from a close affiliation with previous administrations. But city prosecutors have never become mayor. Carlisle’s predecessor, Keith Kaneshiro, announced a bid to run for the city’s top office in 2002 at a time when then-Mayor Harris was expected to resign and run for governor. When Harris bowed out of the gubernatorial race, Kaneshiro opted instead to challenge Carlisle — ultimately unsuccessfully — in the 2004 prosecutor’s race. Of course, there are other cities that have elected former prosecutors. Carlisle also has name-recognition on his side, and he’s the only candidate of the five who can boast having been elected by Honolulu voters four consecutive times since 1996.

DELA CRUZ: The city councilman says his eight years serving on the council make him best-suited to lead the city because he knows how the city works. And, after all, the path he’s following is similar to the path former mayor Mufi Hannemann took to the mayor’s office. Hannemann, too, left City Council to run for mayor. And while he was unsuccessful the first time in 2000, he won on his second try in 2004. Before he was elected in 2002, Dela Cruz worked in public relations while also serving on, and eventually chairing, the Wahiawa Neighborhood Board. In 2003, Dela Cruz was elected the youngest City Council chairman in Honolulu history.

PREVEDOUROS: The civil engineer argues that it’s a positive that he’s not a politician. He sells his experience with urban infrastructure as more important than a political past. Prevedouros likes to remind people that Johnny Wilson, who served as mayor for 17 years, was also a civil engineer. (Wilson worked in construction for Oahu Railway & Land, whereas Prevedouros is running on a strong anti-rail platform.) He’s someone who’s actually written a textbook on the subject he would have to address as mayor. This is his second run for mayor, after an unsuccessful run against Hannemann in 2008.

TAM: The city councilman has managed to win elections over the course of 32 years in city and state politics. But he also carries the whiff of scandal. Most recently, Tam was ordered to pay the city more than $13,000 after a Honolulu Ethics Commission investigation found he mishandled reimbursement requests, and received nearly twice that amount from the City Council’s contingency allowance over a three-year period. The Honolulu Department of the Attorney General is now pursuing a criminal investigation.

Now that we’ve linked this year’s candidates to the history of the mayoral race, here are some questions they might ask to gain further perspective on their chances.

• Have you ever served as a state representative or senator? What about City Council?
  
  This one’s a no-brainer. Political experience begets political experience. Most of Honolulu’s mayors have come to the office by way of some other elected role. Hannemann quit his City Council job for his first mayoral run. His predecessor, Harris, served on the Kauai County Council before taking a city job in Honolulu under Former Mayor Frank Fasi. Before he became mayor, Fasi was a territorial senator and a Honolulu City Council member. Former Mayor Neal Blaisdell was a popular territorial representative and senator before he won the mayoral election in 1954.

• Have you been mayor before?
  Since World War II, just one of Honolulu’s six mayors was not elected to at least a second term. In 1984, Eileen Anderson lost her bid for re-election, and that was so voters could re-elect Fasi to his fourth of six terms.

• Have you already run, and lost?
  
  Fasi was the longest serving mayor in Honolulu history. He headed the city for 22 years over six terms. But it took him almost as long to win his first mayoral election. Hannemann, too, made multiple runs for mayor before getting the job. Still, if persistence is the most important quality in successful campaigning, it’s the reason Fasi served the city in that capacity so long.

• Are you athletic?
  
  In high school, Hannemann played basketball at Iolani. He went on to join the varsity hoops team at Harvard. Blaisdell played college football and even tried out as a pitcher for the Chicago White Sox.

• Are you from Hawaii?
  
  It’s not a requirement, but true kamaaina get bonus points in mayoral elections. In 1954, the Honolulu Star-Bulletin reported it’s part of what enabled Blaisdell to beat Fasi in a close race.

• Are you either for or against rail?
  
  The debate over rail has worked its way through decades of mayoral leadership. Hannemann’s political success is linked in part to his dedication to pushing the rail project. On the other hand, Anderson’s victory in 1980 came in part because she wanted to stop rail from happening. Other perennial issues in the mayoral sphere include management of the sewer systems, trash collection and the preservation or demolition of the Waikiki Natatorium War Memorial.

• Are you a man?
  
  To date, Anderson is the only female mayor in Honolulu history.

• Do you have a catchy nickname?
  These former mayors did: Muliufi “Mufi” Hannemann, Neal “Rusty” Blaisdell, “Fearless Frank” Fasi.

The factors contributing to the outcome of any election are too numerous to track. Today’s checklist illustrates that the past is no clear indicator as to what will happen in the future. Still, we can’t help but take note of how today’s candidates remind us of our political yesterdays.