Prime Minister Chrétien was a very, very skilled and successful retail politician; he 'sold' Canadians what they wanted and they repaid him with their support.
He was also incredibly lucky: Lucien Bouchard and Parson Preston Manning gave him three majorities in a row; there was no way Ontario would have given the Liberals 100 seats had Reform not been (not just portrayed as) an unknown, socially conservative, prairie populist movement with few policies that appealed to the moderate middle.
I didn't like much of anything about Jean Chrétien: I thought and still think that he was, personally, dishonest and that he he used his official power to cover up acts that might have landed a less well connected man in jail; I thought and still think that while his fiscal instincts were right (balanced budget, etc) he chose a sneaky and, ultimately ineffective way of balancing the books - he offloaded the big debt producing programmes to AB, BC and ON; I thought and still think that his foreign and defence policies were based solely and exclusively on domestic political concerns; and I thought and still think that he was and still is a bully.
That being said, he wasn't a bad prime minister, about on a par, perhaps, with Abbott, Thompson and Bowell - not as bad as Trudeau, not as good as Borden or Diefenbaker. But he wasn't a monster and he was what a solid plurality of our fellow Canadians wanted - he was what they bought and they paid for him, too, with the 'northern peso'.