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Tom Brady hasn't officially retired yet, but it likely will happen at some point this offseason. Brady just wants to go out on his terms, and not have Adam Schefter and other reporters reveal that he's retiring.
If Brady ends up retiring like expected, it will set up a Brady and Ben Roethlisberger quarterback Hall of Fame Class in 2027. Brady will obviously get in, there have even been talks that he should go in right away because of his seven Super Bowl rings.
Roethlisberger should be a no-brainer as well, but some people wonder if he'll go in as a first-ballot because of his off-the-field issues. There might be some voters who will bring up his past, but I can't imagine it being enough to not get elected as a first-ballot.
Some have also wondered if they'll allow two quarterbacks in the same Hall of Fame Class, but it's happened twice before, so I don't see that being an issue. According to Gerry Dulac of the Pittsburgh Post-Gazette, since 1967, the two cases where two quarterbacks went in as first-ballot Hall of Fame inductees in the same year were Dan Marino and Steve Young in 2005 and Troy Aikman and Warren Moon in 2006.
The only way that I can't see Roethlisberger being a first-ballot Hall of Famer is if Aaron Rodgers retires, which I absolutely don't think will happen. Roethlisberger has no league MVPs, so they'll give the nod to Rodgers over him. I'm not sure if they'll allow three first-ballot quarterbacks in the same class.