He's done a decent job. Kyle went out and built a Stanley Cup winning team on paper but has nothing to show for it. Dubas went out and traded for Ryan O'Reilly, Nolan Acciari,
Luke Schenn, and more, destroying the Leafs future. But he also made some questionable trades. He passed on Dimitry Orlov and got aging defenseman
Jake McCabe, while also acquiring
Sam Lafferty who he never played. But no manager is perfect. For the term of the contract, I doubt he's taking another short term deal. He could get a lot of money and a long term deal somewhere else, preferably the Pittsburgh Penguins. Or go and rebuild a team.