In 2004, he started a campaign against Tony Clement, suggesting that Clement's wife was an 'abortion nurse.'
Both were running on a social conservative platform, and ironically both were considered to be too right wing to head up the party.
But back in 2002, when Flaherty was campaigning against Ernie Eves, he took dirty politics to a new low.
His attacks on Mr. Eves became so personal, that Bob Runciman was forced to step in to defend the former deputy premier.
Flaherty gets personal with attack on Eves
But then again, I suppose things said during a leadership race can be excused. When Flaherty's wife recently lost her own bid to head up the provincial party, there were no hard feelings, right?
Well that's going to be awkward since his wife will have to work with Hardeman.
While Elliott coped well with defeat, her husband, federal Finance Minister Jim Flaherty, appeared bitter during the crowded celebration at a downtown pub,
astonishing Tories with his demeanour.
Three sources told the Star that Flaherty told Tory MPP Ernie Hardeman (Oxford) to "f--- off" because he hadn't supported Elliott.
Or will it?
See a lot of things are said during leadership races, and then since these people all play on the same team; they dust themselves off, shake hands and turn their attentions to other matters.
So then why are the Reformers trying to use statements made by Justin Trudeau during the 2006 leadership race, against the new Liberal leader?
When the Reformers go on the attack in such a juvenile manner, it shows they clearly have nothing left. And Jason Kenney's contempt for our flag today, at a time when it clearly means something to most Canadians, shows that it's time these guys were sent packing.
The irony is, that this is the eve of the selling out of country to the Americans, so maybe this is Kenney's way of saying goodbye to the Maple Leaf and hello to the Stars and Strips.
And I guess he can drink to that.