The earthshaking news this week of the arrest of Donna Leong, Max Sword, and Roy Amemiya, all former high-ranking officials in the City and County of Honolulu, on conspiracy charges immediately drew the attention of political pundits to the 2022 election.
For a little background focused on one of the three – Roy Amemiya was the Managing Director of the City and County of Honolulu, the second command to the Mayor of the City – at that time Kirk Caldwell. Caldwell has all but formally announced that he will be officially running for Governor in 2022.
Amemiya’s other connection to the election comes as his cousin, Keith Amemiya – who ran for Honolulu City Mayor to replace Caldwell who was termed out – is running for Lieutenant Governor, also on the 2022 ballot. While the jury is still out whether Roy’s connection with Keith, has torpedoed his chances for Lt. Governor, the same cannot be said bout Roy’s connection to Kirk Caldwell, which in many ways could be construed as much tighter.
Tighter, meaning that the fate of one (Roy under indictment) will drag down the other (Kirk for his run as Governor).
In talks around with other pundits, there has been a sense that the connection will direly affect Caldwell for his run for Governor. The most prominent Hawaii political commentator came on television the morning of the arrests, Colin Moore of the University of Hawaii, to say that it will be very difficult now for Caldwell to get enough money and support with this development hanging over his head.
After all, when the guy you appointed to be the second in command for the city is arrested and indicted for a host of charges by the FBI and the Federal Prosecutor, the size of such a development puts shade on all kinds of people, with those getting more the closer you get to the principals.
Others have come up with other theories, which makes sense if you look at Caldwell not as a dead political duck, but as an inconvenient political hot potato that does not go away even if you punt him to the side and tell him to stay. After all, he is not getting the message so far that he is not the most liked person in Hawaii, shown by his difficulty in raising money for a run that is already being called for the current Lt. Governor, Josh Green.
As far as any pundit in Hawaii can see right now, Caldwell will stay in the race, even though it looks more like he will not win the primary.
So, what gives?
CALDWELL has never been seen as someone the political establishment could get rid of by a wave of its hand. Unlike other Mayors of Honolulu that also had images of grandeur – Jeremy Harris and, maybe even Peter Carlisle – Caldwell is not looking or listening to the political games master as he is waving his hand and telling Caldwell your time in the arena is done.
Regardless of how many boos he is getting from the people, he’s still standing there and saying “I want to serve the people more”. This isn’t the first time he has done this, with his prior failed attempts to run and win for Mayor of Honolulu, only for him to keep on trying and finally win two terms in office. That type of persistence is seen as an asset to certain people in this town who want to support a candidate but want to be sure that he will go all the way, regardless of the odds.
Caldwell fits that bill,
Because of that drive, others whom this humble blogger has spoken to in the political realm see that Caldwell may have other avenues to go down, provided the political stars align ever so right, and a lot of people ignore the elephant in the room. He might have enough political capital to be given this opportunity, despite the recent news.
IT’s BEEN WELL KNOWN in political circles in Hawaii that Caldwell has always yearned for a Congressional seat. While he has never run for a seat as a candidate, it’s been said in many circles that his final political career destination has been the Capitol Building in Washington DC, representing Hawaii. Of course, getting one of the two Senate seats is the highest goal, you can be sure if the junior seat in the House comes up, and he is appointed to it, he would be just fine with that.
So, a potential “off-ramp” if you will for Caldwell be based on three “ifs”. The first if would be “if” a seat opens up before the election, Speculation on what seat that will be is going to be left here – because that is all it is right now, speculation.
The second “if” is whether Caldwell’s political ally – current Governor David Ige – is still in office at the time. None of what happens after this comes to pass, as far as the current political landscape – if he is not there. Although the current Governor’s influence has faded, he still could wield influence in the third “if”.
That third “if” is if the State of Hawaii Democratic Party puts Caldwell as one of the three finalists to fill a seat. The process works something like “American Idol” where when there is a vacancy for a seat, a casting call is made to all interested, by the party, to apply for consideration. From that list, three are chosen and sent up to the Governor. This process was most famously drawn out in late 2012 when then-Governor Neil Abercrombie has presented the list, and he chose his Lt. Governor Brian Schatz, one of the three on the list.
All that, come together, and potentially Caldwell becomes Hawaii’s latest representative to Congress. It would also “answer the question” if you will, of what to do about Caldwell with the political cloud above him. It would take him out of consideration for elected office, but as political pundits in Hawai‘i point out, once he is there, he is staying put.
WITH HIM BEING A POLITICAL HOT POTATO, this scenario is, in the eyes of this humble blogger, the best he could hope for at this point. To lose running for Governor would simply add his name to a long list of former Honolulu mayors who also had illusions of higher office, ran and lost. Furthermore, if he continues to press the issue of getting into higher office after his loss, he would then join another, more inglorious list, of political actors who continue to run for offices, only to be taken out again and again in the primaries. Notable local names that are on that list include Mufi Hannemann, Charles Djou, and Colleen Hanabusa.
And if he gets added to that list, it’s been proven as of late that there is not enough political pixie dust to bring a politician back to life with as many marks against them. And if Caldwell thinks his lineage is more in line with current Hawai‘i Congressman Ed Case, who came back after a long spell of being exiled, Kirk Caldwell is no Ed Case.