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Rose entered the 2018-19 season with a new tattoo on his left wrist. He explained the design to Marc Stein of the New York Times in October 2018:
He then rolled up his left sleeve to show off a new tattoo inscribed on his inner wrist.
“The best revenge,” it reads, “is massive success.”
“Do you know who said that?” Rose continued. “Frank Sinatra. And that’s how I’m rollin’. I’m not playing for anyone else. I’m playing for myself. I’m playing for my family. I’m playing for my son and daughter.”
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Rose has a portrait of Malcolm X tattooed on his left leg.Rose was the first player to wear an “I CAN’T BREATHE” shirt in the aftermath of Eric Garner’s death. As reported by Jon Greenberg at the time, Rose was asked if there was a socially conscious athlete he looked up to as a child. Rose responded: “I wouldn’t say an athlete, I would say someone like Malcolm X, someone I looked up to when I was younger… Being so close, him from being from Detroit, my mom paying attention to it, my grandmother always talking about it.”
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A 2011 video interview shows Rose’s new tattoo, the word “HOPE” across his left wrist. For the interview, the 2011 MVP described the emotional impetus for the design: “when things seem like it’s hard, and you think you don’t got no one else on your side, and you feel alone and all that, there’s always a chance and you’ve always got to keep hope alive. And I want to be that hope for kids, for adults or whoever. When they see me, they just want to go hard at whatever they’re doing. Just because they see the way that I am and they see the way that I play.”
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Rose has his mother's name "Brenda" tattooed on the back of his hand. David Aldridge discussed the design during a playoff game between the Bulls and Hawks in May 2011: “Very quickly, on the tattoo, Derrick said that took about 40 minutes to do with the rose and the name "Brenda” over it. He said it hurt so much he actually had to take a Vicodin, but he has no plans on getting rid of it and he enjoys it very much. He wanted to pay tribute to his mom.“
In a video interview from the same year, Rose discussed the first time his mother saw the design: "I got my mom’s name with a rose behind it. Because her last name’s Rose–Brenda Rose–it’s not an ex-girlfriend or anything like that. She told me ‘don’t get it.’ Actually when I showed it to her, it was her and her friend downstairs at her house, I went out there. She said, 'let me look at your hand.’ She looked at my hand and started crying, showing her friend, like 'look at his tattoo’ calling me her little baby.”
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