Cause one of us goes in, and we all go through it
If you mess with one of them, you mess with them all…
Also an allusion to Drake’s classic I’m Goin In, featuring his rap family.
He could also be saying that when one of his crew (cough Weezy cough) goes to prison, they all feel his pain.
And not only Wayne, but also his actual homies. One of Drake’s homies from the OVO set went through a rather large court case, in which Drake spent a lot of money to help with the proceedings. He alluded to this in the intro of Take Care(See 2nd verse of Over My Dead Body)
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