Ever since getting walked on contracts his first year, he has clearly made more good moves than bad. A lot of people are still bitter about that, and the questionable decision to add Tavares but that's now ancient history and not relevant to how he makes his moves today. Its has a cap affect of course but he isn't adding more big $ firepower to further his vision. It did not seem like he thought a club needed more than just scoring when he started out but that has evolved to a more balanced team. I would call it more trial and error than that he had a plan and solved the balance needs over time. More like he admitted what the needs were and then moved to solve them to the extent that he could, He has vastly improved as a GM.
But the elephant in the room will always be the cap because he inherited a team with cap space and then signed an $11M player because a 30g guy as #2C didn't fit his plan. Yes Marleau was signed for too long but that money was already spent and trading a 1st to unload him wasn't necessary until Tavares was added, thats Kyle, not Lou. The burden going forward is the JT contract, not the Marleau one. The strategy was to spend half the cap on 4 forwards and just overwhelm the opposition with their skill while cheap pieces were used for most of the other positions. It hasn't worked yet and he will be running this same game plan into the playoffs for the 4th straight year. Every move he makes is steered by that $40M spend.
If he fails and gets canned it likely will be because he never wavered from his rookie GM cap use strategy. Adding players that make the club better and then not winning before those adds are in decline is a fail. Spezza on the last lap, Gio is turning 39. Simmonds was done when they got him, Muzz may be close to the end, and JT has given them 1 stellar year and three $8M ones. They needed to put the adds in place together and for a couple of years, otherwise you are just keeping your head above water, and adding new value in as old value ages out. When guys like Mikheyev and Spezza are gone we will look back on their high value years and wish the rest of the club was ready when they were.
Having said all the above, every season is a new roll of the dice and we all know the Washington and St Louis Cup wins were not predicted nor were the pundits touting their roster building as enlightened. We don't know what the club would have done last season but for the Chariot knee, and if last seasons Campbell wakes up for the playoffs a top 5 team has to have a real chance. If they win or make a deep run that is a vindication of the Dubas roadmap. Now if they fail miserably because management didn't make a goalie move, or they just get outplayed by enough to lose in round 1 again I am not sure that would indicate the present regime has earned another chance.
Lets go Jack!