It seems the real challenge here is coming up with the highest number of hops. I have two 4s so far with "pro plus" and "smallholder" but haven't been able to eek out a 5 or higher..
Five: APPL -> Area Police/Private_Security_Liaison -> Police science -> Jurisprudence -> 1940 -> Adolf Hitler.
It started as a game on 4chan or someplace similar - pick a random article and see how quickly you could get there, or alternatively think up the one that would require the most connections. That in turn has origins going back to the days of aristocracy, when degrees of (blood) relatedness in books like Debrett's peerage were of great importance for evaluating marriage proposals among the gentry.
I wasn't able to find more than four until I tried "Justin Bieber", which returned no results. I guess that means it hasn't found a path for Justin Bieber yet?
I think his dataset is out of date and so the Justin Bieber article doesn't exist.
I'm not getting no results for "Debug port", which should be no more than 3 (since it links to Xbox, which is 2).
Same for "Index of Estonia-related articles".
I think that means there are no hops to be made. Draw your own conclusion.