re: JFF to Browns, AJ to Bengals = who ends career first?

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Cincinnati has at least been to a couple of Super Bowls and almost won in their last appearance

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You are confusing the reign of the father with the joke the son has made of his dad's team.

Since Brown became owner, the team has had only 5 winning seasons out of 23 and has a winning percentage of .403 (151-224-1) in the regular season and .000 (0-5) in the playoffs. In 2008, the Bengals set a record for the most games needed under one specific owner to attain 100 wins (288). In 2010, the team set a record for the least games needed to lose 200 (both considering and not considering playoffs) under one specific owner (314).

The Bengals hold a number of distinctions for the time frame of Brown's ownership: It is the only team with three nine-game-or-more losing streaks. It also holds six of the twenty-five 0-6 starts (24%) and four of the thirteen 0-8 starts (31%) in that time. The Bengals have gone winless in October nine different times in twenty-two years under five different head coaches (Sam Wyche was originally hired by Paul Brown).

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Cleveland is where careers go to die before they even start.

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I would say the same for the Bungles under Mike. It is interesting to note that his dad won with both the Browns and the Bengals while he was at each team.