Caldwell is in a big mess of his own making. He has been there at the City longer than almost ANYONE -working originally for Mufi as city director, then becoming acting mayor in 2010. Rail was always Priority No. 1. He knows every detail of it (or should.)
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Caldwell OWNS Rail and PRP, Move Oahu Forward, etc own Caldwell. He sold his soul to the devil to beat Cayetano. He promised On Time and On Budget. 
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Having followed rail details for many years and as consulting party to HART, it is amazing that no one I can think of is still at HART or the City, involving Rail- than Caldwell. He OWNS the rail fiasco and it will bring his political career down forever as there is no escaping what a huge mess it is and how it will only get MUCH WORSE in the future.
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Rail always was and always is a Land Development project. Rail is just a loss leader to show an elevated railway gliding through the countryside for sales brochures and videos to sell land and condos. "Commuter Rail" is a big lie.