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One of football’s most decorated players at the professional and collegiate levels, Woodson played 18 seasons in the NFL with the Oakland Raiders and Green Bay Packers, racking up a list of accolades including Super Bowl XLV champion, 2009 Defensive Player of the Year, 1998 Defensive Rookie of the Year and the 2015 Art Rooney Sportsmanship Award. He was elected to the Pro Football Hall of Fame in 2021, his first year on the ballot, and enshrined in Canton that August. 

Ryan starts the conversation off by quoting Charles on an important message that he shared during his Hall of Fame speech, and asking the significance of the line, "They say a woman can’t raise a man, I call bullcrap, because my mom raised two men." Charles shares why it was important for him to put that message out to the world and let him serve as proof that strong men can be raised in single mother households and talks about his own experience of being raised by his mother and how his work ethic and his will to never give up is all from watching his mom and the values she instilled in him. As hard as the NFL is and as many ups and downs, injuries, bad days and the days that make you want to walk away, Charles always remained grounded by his mother's efforts and life approach which he used to sustain his own success. Channing doesn't miss a moment in poking a little fun at Charles' singing comparing him to Demarcus Ware's recent performance, as Charles chose to sing a tribute for his mother at his Hall of Fame induction which gives the guys some material for a fun conversation. 

Prior to his professional career, Woodson was a two-time All-American at Michigan and led the Wolverines to an undefeated season and national championship in 1997, the same year he became the only individual to win the Heisman Trophy while playing on both sides of the ball. Fred asks about playing with Tom Brady during those years at college and what type of player he was then and the difference in Brady during the early years vs becoming one of the best to ever play in the NFL. With all the surrounding controversy around Michigan football today, Woodson remains loyal to the program and doesn't find any foul play with the information he is aware of that's gone on. 

Woodson goes on to talk about his own NFL career and later on playing against his college teammate sharing how a day doesn't go by where someone doesn't ask him about the infamous loss to Brady in the 2002 postseason, where Charles sacked Tom who fumbled to seal the win for the Raiders yet, it was overturned due to the "Tuck rule" and the Patriots went onto win. A moment that haunted Woodson for years which is why winning the Super Bowl with Green Bay Packers meant so much to him later on in his NFL tenure. Talking about how some of the greatest cornerbacks are often compared to Woodson, he reiterates how and why people view him as one of the greatest defensive players to step on the field with no argument on this from Ryan, Fred or Channing as they reiterate Woodson's achievements and go on to say that he himself often looks back at some of the things he did, and can't believe he did it either. 
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