"I'm here for one reason: I'm here to support my brother Meek Mill. This requires more than just gradual reform in laws-It requires a swift overhaul", Kaepernick tweeted on Monday.
Mill's sentence has sparked a debate on criminal justice, with numerous Philadelphia-born supporters arguing the sentence is a reminder that many Americans, in particular black men, receive unfair sentences.
Mill had been on probation from a 2008 gun and drug case. The sentence has been criticized for its length and the credibility of claims he violated his probation.
According to reports, the Federal Bureau of Investigation is looking into the judge responsible for sending Meek to prison.
Lawyers for imprisoned Philadelphia-born rapper Meek Mill have launched what one lawyer called a "flurry of legal filings" to try to get the 30-year-old hip-hop star released from his 2- to 4-year prison term for violating the terms of his 10-year-old probation.
Carmen Perez: The biggest incongruities of this case is that this young man who has worked so hard on behalf of his community, getting clean and contributing back - has had so-called "probation offenses" dogging him for more than 10 years.
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Tacopina later added that Meek is "a strong kid" and his community will stop at nothing to ensure justice is served. "JAY-Z is out there going absolutely wild", he continued.
Brinkley's office did not respond to a request for comment and instead referred CNN's request to Gabriel Roberts, a spokesman for the 1st Judicial District of Pennsylvania, which declined to comment as the matter is "subject to future litigation".
"She's enamored with him", Tacopina tells Billboard.
Meek Mill's lawyer Joe Tacopina previously claimed that she requested for him to make a remix of Boyz II Men's song "On Bended Knee".
Asked what his plan is if both motions fail, Tacopina said he would then "go the appellate route" and file a formal appeal. Mill is signed to Ross' Maybach Music Group.
At the November 6 hearing during which Brinkley sentenced Mill, the veteran judge recounted nearly 10 years of court proceedings in which he had violated his probation, and she had sentenced him to short periods in jail and then had extended his probation. "I want y'all to understand that if it take Meek Mill to draw this attention, we gonna use Meek Mill to draw this attention that is gonna speak for so many others", Rozay said at the rally.