A great deal can happen in five years. Just think about what the world looked like five years ago. Finding Dory dominated box offices. The Pittsburgh Penguins had just won the first of their back-to-back titles. The 2016 NHL draft class had just finished their moment in the limelight. The Jets thought they nabbed the best pure finisher since Alexander Ovechkin in Patrik Laine, a player to build around for a decade-plus; he's long gone now. The Canucks selected Olli Juolevi with the fifth overall pick; he was just moved for spare parts to avoid the waiver wire. 

The free agent pool is even more damning. Milan Lucic, Loui Eriksson, Andrew Ladd, Kyle Okposo and Frans Nielsen all signed deals for six to seven years and $5.25-6 million per. Precisely zero of those deals worked out for the teams that signed them.

On a more personal note, I have far more grey hairs now than I did back in 2016. I also hurt my wrist getting out of bed the other day. Things happen quickly.

It's why we don't get too far ahead of ourselves in Fantasy Hockey. Even in deep keeper leagues, it's the teams that focus on winning in the immediate future that find the most success. Building long-term is a path that is fraught with pitfalls.

All that comes together to make this particular exercise that much more challenging, but also enjoyable.

Today, we're going to investigate the best players to own in a keeper league ahead of the 2026-27 season. Some of these players you'll have obviously heard of, and many possess value today. Some are just young kids on the way up. Others haven't even landed their driver's licenses yet. I'll preface that the biggest salty thing to remember is that this involves an enormous amount of guesswork. We'll look back on this piece in five years and laugh at some of the spots. But hopefully, we'll nod knowingly at a few more.

Also, remember that I have it out for/am overly biased towards your favourite team and player and that is why they land so low or high on this list. It's just the way it is.  

Without further adieu, I present to you the top 50 fantasy hockey league keepers to try and get ahead of the 2026-27 season.