Here's how I envision things unfolding over the rest of this season, the off-season, and over the next season (short term).
Leafs continue to play .500 hockey through January, mounts a surge in February and March, and sit comfortably in the 1st wildcard spot by the end of April, making the playoffs and facing off against, likely, Tampa Bay.
Leafs split games in TB, and go on to win a surprising round 1 match-up in 6 games.
They face probably Washington or NYR in round two, and lose in 6 games.
During the off-season, the Leafs hire Mike Babcock as their new head coach.
Babcock begins his process of evaluating players during the off-season, doing a meet-and-greet with the players and some key prospects. The trip through Massachusetts is skipped, which strikes up a media firestorm of speculation that Kessel is going to get traded.
Sure enough, during the Draft 2015, the Leafs ship Kessel off to a western conference team, bringing back a top defensive prospect and a 1st in 2015 (it's a 18-21 pick). Not sure which team, but one of STL, NSH, SJS, or ANA would be my guesses.
Lupul also gets moved out. Leafs re-sign Franson, Bernier, Kadri, Winnik, Santorelli, and Holzer.
Everyone expecting Phaneuf to be jettisoned are puzzled that he is still on the team when training camp opens up.
Surprise addition in training camp is Broll nabbing a roster spot out of the gate. Of course, the biggest surprise is moving Gardiner up to LW, Ã la Brent Burns/Dustin Byfuglien.
Game day roster is as follows:
van Riemsdyk - Kadri - Holland
Gardiner - Bozak - Clarkson
Winnik - Santorelli - Broll
Panik - Komarov - Leivo
Phaneuf - Franson
Rielly - Robidas
Polak - Defensive prospect acquired in Kessel deal
Holzer
Bernier
Reimer
Under a new coach with a possession-based mindset, and a renewed commitment to defensive hockey, the Leafs become one of the top possession teams in the NHL, with the Kadri line being one of the top in the league. The Winnik/Santorelli/Broll line becomes one of the top shut-down lines in the league, amassing a crushing +85 +/- rating collectively.
Holland posts a career-high 25 goals and 30 assists as a winger on the top scoring line.
Fans are ecstatic and see the Leafs go on to post solid finishes over the next 3 seasons, placing 3rd in the division in each year, and making it to either the second round (twice) or conference final (once) during that span.
Under the new regime, draft picks flourish, and the Leafs make major breakthroughs in forensic analytics, and break-open the moneypuck system on an unprecedented scale.