I've taken draft class data from 2003 to 2016, with career games played and points, and cup winners from 2004 to 2018 to give a visual representation how each Draft Class compares to each other as well as give a breakdown of which teams have accumulated the most amount of First Liners/Top 4 D/Starters in the last decade of drafting.

Feel free to offer thoughts/feedback!

Link to the dataset is here if you want to filter to your team specifically or see the names (hover your mouse over the points)

Source: Hockey-reference.com
NHL Entry and Amateur Draft History | Hockey-Reference.com (draft classes)
NHL Stanley Cup Winners | Hockey-Reference.com (Cup winning rosters)

My Arbitrary Criteria for evaluating a player
1st liner =
Must have over 50 games played in the NHL and must be producing at a 0.6 career PPG
Top 4 offensive defenseman = Over 50 games played in the NHL and producing a career 0.4 PPG
Starting Goalie = over 200 NHL starts

Cup winners (2004 to 2018) = are based on whether the person has appeared on the 23 man rosters that cup winning teams carried into the playoffs. On average it takes a drafted player 6.4 years after their draft year to win the cup. Ovie being one of the outliers by taking 14 years!

1st page represents highlights which picks qualify as playing over 82 games, or are 1st liners/top 4 offensive D and starters. You can also filter this to your teams.
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2nd page is the cumulative results for all the teams from the 2003-2016 and which teams were the best at drafting Top 4 offensive D, First liners and starting goal tenders.
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