Brinkley also noted that Williams, 27, failed to provide his probation officer with a working phone number, posted disparaging remarks on Twitter about the probation officer and the prosecutor assigned to his case, was "combative" and "disrespectful" to probation staffers during a May 15 meeting and posed for a picture posted on Instagram holding a gun while two other men also held guns.
"After all these years of me trying to help him move his career forward . . . I believe he is thumbing his nose at me and at the probation office," said a frustrated Brinkley, who placed the rapper on probation in 2009 instead of sentencing him to five to 10 years in prison after a gun and drug-dealing conviction.
"Sir, I really didn't want to do this but you made me do it," added the judge, who rejected defense lawyer Gary Silver's request for his client to be allowed to go home to get his affairs in order.
Instead, a deputy sheriff ordered Mill to empty his pockets before he was escorted to jail, leaving behind his downcast entourage.
Silver had argued that the gun in the photo was a prop and that Mill's cellphone did work, at times.
Mill, who received glowing praise from his etiquette teacher, Gail Madison, during court hearings last September and this February, meekly asked Brinkley not to send him to jail because he had to earn money to provide for his son and other family members. She suggested that the judge instead suspend his ability to travel out of town - which Brinkley did for a month in 2012 as punishment for probation violations.
Going to jail, the rapper said, "will damage everything I got going on in my life, everything I've worked for in the last six years."
But Assistant District Attorney Noel Ann DeSantis - whom Mill called a "racist" on Twitter - said jail is where he belongs. She asked the judge to impose his original five-to-10-year sentence.
"I think the judge made clear in her analysis that she gave the defendant every opportunity to do well and the defendant continued to thumb his nose at this court," DeSantis told reporters. "He did not really take seriously that his probation was a gift and was really for him to be able to have his career."
Brinkley told Mill she believed he had the talent to be as successful as rap star Jay Z, but lamented he had let down her and his fans.
"Of all the people who have come before me, I knew you had a shot to make it in this business," the judge said.
Her order means Mill will miss - among other gigs - his "Homecoming Concert" at Temple University's Liacouras Center next Saturday.
On Twitter: @MensahDean