Steven Stamkos hits 500 goals, Connor McDavid's placement on the NHL99 list, what does a realistic extension for Cole Caufield look like?

To kick off, Ian and Sean have some important NFL business to attend to before discussing Steven Stamkos hitting the 500-goal benchmark. In what tier does he sit in among the all-time greats? Next as The Athletic's NHL99 project rolls on, thoughts on Connor McDavid checking in a #16, and the difficulty in placing players that still active in the league. Then, as the Canadiens look to extend Cole Caufield, what a reasonable contact for him may look like.

Jesse Granger then jumps on for "Granger Things" to discuss his goalie mask rankings, and what team is a good bet for betting the over on in games. Then to wrap up, they hit the listener mailbag and take a look back with "This Week in Hockey History".

Have a question for Ian and Sean? Email [email protected] or you can leave a voicemail at (845) 445-8459!

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