This raises massive questions about his honesty, integrity, judgement and competence. He's either lying about not identifying a potential conflict of interest, or an imbecile for not spotting it and sorting it when he was given the transport job back in 2002.
Strangely, his shifty behaviour seems to have been okayed by the fact he probably lost $49,000 on the sale. Somehow, the un-logic hgoes, this makes it alright. He obviously wasn't being dishonest, just klutzish. After all, a clever schemer wouldn't have been dumb enough to lose that much money, right?
A clever schemer, in fact, would have had the sense to realise the long game was more important. Rather than clinging onto shares that were never going to realise a profit, they would have ditched them immediately the political opportunity opened up. Also, not selling them earlier suggests a lack of financial judgment - an astute investor would have cut their loses by selling before Key did. In spite of what the media are implying, bungling your finances to your own detriment doesn't indicate honest. Rogues can be fools as well.
The fact that Key hung onto the shares as long as he did only shows you can have poor judgement, no principles and be incompetent, all at the same time. Just like David Benson-Pope.
1 - 'Key lost $49,000 on sale of rail shares ,' by Colin Espiner in The Press, 5th of July, 2008. (http://www.stuff.co.nz/4608005a6160.html)