If you want to classify the Plekanec and Boyle deals as competitive playoff moves, I'm fine with that. That's something all GM's do when they are competitive, including Dubas. I don't think you should be paying 2nd round picks for 4th liners, just like I did not like having to pay for Clifford, but maybe that is just me. At the same time though, Dubas shouldn't be criticized for letting Gardiner, Barrie, JvR, Bozak, Komarov, etc. go for nothing since they were rentals when we were competing too.
--- Unrelated to original thread below here ---
Everyone knew the Leafs were getting value out of Phaneuf and their UFA's. He had an overpaid top 4 defenseman who was still very useful at the time, and helped Ottawa get far into the playoffs, and used his financial muscle by taking on a bunch of overpaid deals and taking less (arguably a lot less) trade value in lieu of retention. He traded his UFA's for market value, which is the minimum of what Dubas has been able to manage to receive in the vast majority of his trades. BTW, Dubas was the one who got a lot of that "found money" for Lou. He was the one who went bargain bin hunting, bringing back Winnik, acquiring Spaling in the Kessel trade, signing Matthias, PA Parenteau, etc. for Lou to be able to trade before Lou was even made GM.
He signed Rielly and Kadri to market-value deals. He bet on both of them and their potential and shockingly, as is the case with the vast majority of RFA's, they grew into it. In fact, it took Rielly a year to grow into it. However Dubas does the same thing with higher end guys and suddenly he is a pariah for messing up the cap, despite having literally all of the RFA's except Marner grow into, or exceed, their contracts within one year? However does not shock me at all. Happens all the time with high end RFA's (i.e. Drasaitl, Eichel, etc.).
His best move was, as I said, getting a goalie. He overpaid, but good for him. That's what he's been able to do well in New York too. He was hardly the worst GM we've ever had. He was certainly better than Nonis and Burke, and I would rather have him back than using Hunter. However the largest driver of his success was lucking out on Matthews and having him, Marner and Nylander on an ELC for much of his successful tenure. He was fine, but fine is not winning us Cups. Dubas is much better than fine and gives us a much better chance at winning a Cup than him.