Some of Pendlebury's deserved stature comes from external influences of team success earlier in his career (8 straight finals appearances resulting in a couple of Grand Finals and a flag), coupled with having the public profile of playing for Collingwood.Very good player but the OP is dreaming if he thinks Boak is on the level of Pendlebury. Pendlebury is rated very highly and is still underrated. Watch the Pies go to pieces when he retires.
Being in Adelaide for a less successful team, Boak compares unfavorably. The Adelaide bit especially, only have to look at how even a genuine superstar like Tredrea was never lauded in Melbourne like he should (yes I was living there and I could see it first hand)
Whilst not up to Pendlebury' s level, (possibly) a Brownlow and (less possibly) a premiership this year might close the gap career wise.