Being bad is not hard. If Leafs get rid of Kessel and Phaneuf, they go from 5-15 in draft to bottom 5. They can still keep Kadri, Rielly, Nylander, Bernier, Gauthier, etc. This being the NEW core in addition to picks/prospects they pick up in next 3 years. This new core should be aiming to win a cup in next 5-10 yrs. Just keep these young guys around and let them grow.
Assuming Rielly and Nylander continue to develop and Bernier and Kadri continue to play at or above their current level, that core playing literally any system that doesn't promote getting heavily out-shot every game is too good to out-tank teams with little high-end NHL talent, or high-end talent condensed in one area in the game (like Edmonton). If you want to tank with that core, you need to surround those 4 or 5 players with AHL-level talent for multiple years, and that probably ruins the developing players and extremely devalues the established NHL talent. Not worth it.
Again, being bad is not hard. Buffalo will be bottom 3 this year.
Buffalo finishes third-last and there is a 88.5% chance they end up without McDavid or Eichel. If the season ended today they would have spent the last year and a half trying to get one of those two players and have only a 10% chance at first pick. Being "bad" might not be hard, but being bad enough to get what you want sure is.
The reason Leafs did not finish bottom 5 in a lot of years is because they were doing stupid stuff, like starting Martin Gerber in meaningless games down the stretch in search of the 8th playoff spot in the East.
That's some revisionist history. Gerber put up a .905sv% and 3.23 GAA in 12 starts, which is awful and was barely an upgrade on an injured Toskala (.891, 3.26). They weren't trying to make the playoffs when they acquired him, they were grabbing a replacement-level goalie. His record ended up being decent because the team in front of him scored a ton of goals. They should have iced worse players then? Boyd Devereaux scored a hat-trick in the final game of the season (and his last NHL game) to leap-frog LA and Phoenix. Not much you can do about that - they iced crappy players and still won because other teams were also icing crappy players.
The reason Kessel and JVR are on the Leafs is because other teams didn't want them.
That is false. Trading players doesn't necessarily mean you don't want them. Boston had cap issues and couldn't afford Kessel unless they either gutted their roster or got him to take a bridge deal; Kessel and the team didn't have the best relationship but he was traded because he yielded a massive return and let the Bruins keep the rest of their team intact (and having TOR's 1st round pick allowed them to trade their own 1st in a package for Nathan Horton). Boston traded Seguin for similar reasons. It was also reported that NSH and NYR offered BOS significant packages for Kessel, so it wasn't like he was unwanted. His value was high and dictated by the offer-sheet he was eligible to sign so TOR, NSH and NYR must have really wanted him.
JVR is on the Leafs because PHI had too much cap-space tied up in their forward core and wanted to redistribute assets. They misjudged Schenn's value. JVR is a high-end player and has significant value at his cap-hit - if he was on the market teams would be lining up.
As good as they are, they are not Toews, Kane, Malkin, or a Doughty--these types of players do not become available by trade. only through the draft will you snag one.
Great players do become available by trade in certain circumstances (Thornton, Nash, Kovalchuk, Seguin). Toews, Kane, Malkin, Crosby, Stamkos and Doughty haven't become available (or tried to leave their club) because they have been compensated fairly and play on contenders with many high-end players - teams that are so good that they could still be competitive even if they lost one of their superstars, as evidenced by Pittsburgh's record when Malkin and/or Crosby are out of the lineup. Chicago and Pittsburgh basically lucked into multiple superstars by getting the best player in back-to-back drafts, which isn't a very reliable strategy.
It's possible to be successful without a top-5 player in the world and it's not worth perpetually gutting your roster for the small chance of getting one at the top of the draft. I'd argue you have a better chance of snagging one of the league's top players by building a desirable team to play for and waiting for the rare time one of those players becomes available than you do trying to tank strategically.
If the Leafs had long ago decided to suck it up and not continuously go for a quicky rebuild they would have that coveted #1 centre (Seguin) by now and likely be much farther ahead. Oh and they would also have a franchise goalie by the name of Rask.
Those two players are pretty good examples of how you can acquire franchise players without tanking. They are also good examples of how teams with multiple franchise players can struggle if the
The past decade has been pissed away trying to rebuild without taking the time to do it properly.
The issue hasn't been not committing to a full-out rebuild, the issue has been employing incompetent people who piss away good assets and can't identify and fix the biggest issues. The past ten years has seen decent teams lost to goaltending and good goaltending wasted by a team that voluntarily gets outshot every game. Having these people eagerly destroy/disgard assets were lost to abysmal goaltending (e.g. not being able to fix the goaltending between 2006 and 2012, not being able to identify systemic issues from 2012-15). The results have been poor but the teams While the results have been poor, 2006-2012 was decent teams playing in front of abysmal goaltending, while 2012-15 has been abysmal teams playing in front of great goaltending. For years the skaters The results have been awful The next decade is going to be pissed away because Phil and Dion are not going to get this franchise anywhere. There is no Stamkos that is going to drop in via free agency to lead this team. So if the goal is a Cup, you ditch Phil and Dion and let the chips fall where they may. Because you know as well as I do that Phil and Dion are not going to lead this team to a Cup no matter who you surround them with.
So trading Phil and Dion is more about simply starting over and maximizing assets. The alternative is almost certainly continued mediocrity.