64. Boomer Esiason (Cincinnati Bengals 1984-1992, 1997, New York Jets 1993-1995, Arizona Cardinals 1996)
3rd Place Bengals QB and 3rd Place Jets QB
Career Record 82-90-0 (47.67%) 76th out of 102
Record in Games with Good Defense 52-24-0 (68.42%) 84th out of 102
Record in Games with Bad Defense 30-66-0 (31.25%) 34th out of 102
Percentage of Games with Good Defense 76/172 (44.19%) 80th out of 102 (+16)
Wins Above Average in a 16 Game Season (0.260)
Yes, Boomer Esiason once played football in the NFL. Surprising, huh. He's more or less been relegated to being CBS' angry talking head complaining about the good ol days of football. Lo and behold, he was actually a somewhat decent player. He did make the super bowl once in his career after all. The Bengals made a very smooth transition from Ken Anderson to Boomer. He was actually the first QB selected in his draft class, taken 38th overall by the Bengals. Nowadays it'd take a minor miracle for the best QB of a draft class to fall to 38, even if you're literally drafting JaMarcus Russell and Brady Quinn. In any case, Boomer came into the league with a chip on his shoulder, and combining some of the philosophies of the West Coast Offense, the Bengals ran the no huddle offense to perfection in Esaison's time. The Bengals had some ups and downs early, but their greatest chance at winning a super bowl came in 1988, when after coming off of a 12-4 regular season, the Bengals and their offense bullied the Seahawks and Bills to make it to the super bowl. If not for the last second heroics of Joe Montana and John Taylor, Boomer would have had a super bowl ring. The Bengals never got another chance like that again. They snuck into the postseason as a 9-7 division winner in 1990, but by that time teams had figured out the no huddle and Boomer was starting to develop a penchant for throwing to the wrong team. The Raiders kicked them out in the divisional round, and the Bengals have not won a playoff game since. The Bengals started to disintegrate after that, and Boomer wasn't left with much help on offense or defense. Eventually the Bengals decided to go with a different direction at quarterback, shipping Boomer off to the Rich Kotite Jets. The 90's were basically just full of misery for Boomer as he had no help, and kept putting his team in holes he couldn't dig himself out of. He suffered a nasty concussion in 1995, and was probably the beginning of the league actually looking into the effects of concussions (and subsequently sweeping them under the rug). He went to Arizona as a free agent in 1996, and returned to the Bengals in 97, looking almost like his former self before taking another nasty concussion and being forced to retire.
Boomer has some of the worst defenses on this list, playing for the slumping Bengals for a good chunk of the 90's as well as the Kotite Jets, who might have given the Bengals a running for the worst team of that time period. Despite that, his record in games with bad defenses is actually really good, and part of the reason he can still stay above average despite having a really rough second half to his career. The issue was he was also prone to giving it away later in his career, no doubt due to all of the CTE he's endured throughout his career. One only needs to watch him on CBS to see how the game has affected his mind. Truly a tragedy, if the league never befell him, maybe he wouldn't be such an asshole.