Those who cannot remember the past are condemned to repeat it
- George Santayana
The reason for the above quote? BigFooty has a serious problem seeing past current form when assessing future prospects.
No team having to conform to equalisational policies of the AFL has EVER managed to win three flags from a single core side. Collingwood have a monumental task ahead of them to win three flags from this side.
Whilst odds are reasonable that they can win another and get to sixteen, history would show us that the seventeenth is unlikely before the inevitable fall and rebuild.
So that would leave Essendon and Carlton to race to a flag and of course the seventeenth.
Just like to copy and paste a line for impact purposes:
BigFooty has a serious problem seeing past current form when assessing future prospects.
Never more apparent than the 'rate clubs lists' threads, which almost always come out resembling something akin to the ladder at the time. Whilst several people on this site are quite insightful, the masses cannot see past current day form.
Carlton DO NOT have a list capable of challenging for a flag prior to a rebuild. Essendon DO have a list capable of challenging for a flag prior to a rebuild.
Thus, to answer the OP, Essendon is the likeliest of the three to reach a seventeenth flag first.