With all due respect no Prime Minister in Canadian history except for maybe Diefenbaker had a worst record and relationship with a US President than Harper .  His handling of the "no brainer" Keystone was a disaster as well as every thing he did with the Americans. 

We do not know at this point how Trudeau will do with Trump so I hesitate to prejudge , however it cannot be much worse than Harper. Also keep in mind that Trudeau has brought on Mulroney as an adviser who knows Trump and is very well connected to the GOP.