Julie Hardaker, says Bossy, is the hardest-working mayor he's worked with. David Braithwaite is easily his least favourite. The two clashed over Bossy's determined fight to secure Waikato Stadium for the city.
Bossy formed "Friends of the Stadium" to capture signatures for a referendum. He secured 18,000 signatures and raised thousands of dollars to fight the campaign.
He was honoured last month by being named a patron of Waikato Stadium after the council's newly revised civic honours policy allowed for the appointment of individuals as patrons of city facilities or projects.
His battle for the stadium isn't the only string to his bow; he fought to have the Rangiriri restored and celebrated as part of the city's heritage, and has contributed much to Anzac Day commemorations and helped build the city's civic relationship with Ypres in Belgium.
But don't ask Bossy what he thinks his finest achievement has been. "If you have to tell people how powerful you are, you aren't. If you have tell people you have mana, you don't."
That tall poppy syndrome was probably fostered during Bossy's time in the army. And that is where the two Peters first met.
They were taking part in an operation in Woodhill Forest north-west of Auckland when they came across each other.
Peter, a draughtsman at NDA Engineering, a husband, father of five and grandfather of one, has been making submissions to the council about aspects of cycling for years.
He decided it was time to throw his hat in the ring this time. If he's elected he doesn't intend "to force change quickly". He's a strong supporter of the safer speed zones and thinks there's room to do away with anything at council that "adds unnecessary cost, waste or time without adding value".
Time will tell if Peter H is elected and Bossy is keen to see how the city will continue to grow and what sort of governance will be in place in years to come. "Will we be a city or a region?" he says, referring to the Mayoral Forum and the potential for a merger with neighbouring councils.
While he admits he's made mistakes, Bossy says it's been an honour to have helped lead and shape the city for the past 15 years.
And Bossy's advice to his namesake: "If you work at Affco, you will get some blood on yourself. If you work at waste water treatment, you will get some poo on yourself. If you're a city councillor and take everything personally, you don't understand the role.
"It's all about how you handle it; politics can be cruel at times. Keep a sense of humour, value the staff for their input and advice and you can afford to lose ambushes as long as you win the battle."