The horse was paying odds of $51 to win. But for a pragmatic man, Mr Key has a suspicious side. Clearly wary that a win by Drunken Sailor would be an omen for the election, he put a bet on the horse to place, saying the best outcome was for the poor old horse to come second.
Even more spookily, Mr Key had also drawn Drunken Sailor in his office sweepstake - so, being a wise investor, he diversified his portfolio by putting another bet on Niwot.
Unfortunately, Drunken Sailor finished 12th.
But neither of Mr Goff's picks - Precedence and Tullamore - came in and it was no doubt some consolation to Mr Key that the horse which did come second was Red Cadeaux - Labour's colour. Mr Key's usual luck might have taken a day off, but he will not look a gift horse in the mouth.
On his day in Hamilton, Mr Key donned a high-visibility vest and hard hat at the Te Rapa bypass roadworks, joking that he had needed the hard hat for the leaders' debate the night before.
There was some discussion about engineering standards and the earthquake tolerance of the overbridges. But Mr Key's main topic was Sonny Bill Williams and his signing by the Chiefs - the local team for Hamilton.
One construction worker observed that at least with the Chiefs - unlike the All Blacks - Williams was more likely to play a full game rather thanbe made to sit on the bench until the last five minutes as he did with the All Blacks.
Mr Key agreed, saying Williams was "a bit too expensive to play for five minutes".
The Prime Minister then announced that the Sonny Bill Williams policy would be extended to beneficiaries - no longer could they sit on the bench, they too had to go in search of the ball on the field.