2015-16 - Finish near the bottom of the league (25th-30th)
2016-17 - Competing for a wild card position, finish between (7th-10th)
2017-18 - Finish 3rd in our division (1st round playoff loss)
2018-19 - Finish 2nd/3rd in our division (1st round playoff loss)
2019-20 - Finish 2nd in our divison (2nd/3rd round exit)
2020-21 - Compete for 1st in our division, finally a contender (conference final/cup final)
2021-22 - Compete for 1st in our division, remain a contender (conference final/cup final)
I expect current coaching and management to attract a lot of strong players. I trust their skills in drafting high end talent and acquiring players that will help us become a contender. Nylander/Marner will become strong impact players by that time. We will have a very impressive surprise prospect crack the big squad. Rielly will be a seasoned veteran by that time, and our core will look very different from what it is today.
JVR, Marner, Nylander, Rielly, Gardiner, Percy, Dermott, Kapanen, 2016 1st round pick, Stammer
maybe ? I don't expect Kadri, Phaneuf or Lupul to be around by the time this team is ready to become a cup contender.