Oh, when it rains, it pours.

With only five days left before lock-down begins for getting caught with drugs in his vehicle last month, rapper T.I.'s days of freedom are numbered. As if that wasn't enough, his destructive choices have caused him to lose endorsement deals. The road to redemption has been outright rocky to say the least for T.I., and the pit-stop back to prison is a costly one.

• T.I. Arrested: Rapper Clifford Harris and Wife Face Felony Drug Charges
• T.I. Arrested: Lawyers Negotiate 6 Month Prison Plea for Drug Bust
• Rapper T.I. Denies Using Stranger's Suicide Attempt as Publicity Stunt

The hip-hop celeb, whose real name is Clifford Harris, Jr., will be facing an 11-month sentence for violating his supervised federal probation from previous weapons charges, after he and wife, Tameka "Tiny" Cottle, were arrested September 1st on drug charges. Los Angeles police found codeine, ecstasy and marijuana in the couple's vehicle and the Grammy Award–winner tested positive for opiates.

Although T.I. pleaded for leniency with an Atlanta judge, admitting to the court that he is battling a drug addiction, the rapper-turned-actor was given an 11-month sentence nonetheless to begin Nov. 1.

The ruling came on the heels of a situation that put the 30-year-old back in the spotlight first positively, then negatively. T.I. made headlines for talking a suicide victim off the ledge of an Atlanta skyscraper on October 13th. When the "rescue" happened, T.I. was praised for his involvement, but then tongues started wagging that perhaps the good deed was just a publicity stunt. Critics speculated that the timing of the incident was coincidentally ahead of his key court appearance for his drug bust.

T.I.'s bouts with the law have also resulted in a loss of millions. The gig as the Axe Body Spray spokesperson fell by the wayside as soon as it was announced that T.I. would be prison-bound again. Now the high-profile endorsement with Rémy Martin cognac was pulled out from under him as well, just five months after he inked a deal with them. The spirits company released a statement with regards to their now-severed contract with T.I.:

"Sometimes the 'road to redemption' is a difficult path," read a statement from the high-end cognac-maker. "Regrettably, we will not be able to continue collaborating with T.I. at this time. We wish T.I. well and hope he will devote his time and energy to staying the course."

On the flip side, T.I., who had planned on releasing his latest CD before his prison stint, actually renamed it from "King Uncaged" to "No Mercy." Now, the CD's release is shelved until further notice. I wonder what he's exactly referring with the title switch; the justice system having no mercy or the range of his musical gifts as a rapper having no mercy on the public?

Anywho, the clock starts ticking now....