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Beyond the fact that the album was absolutely banana's...
Listening to it he had everything needed to Win.
Reason he didn't win: COOPERATION.
Had Shawn agreed to do the "Big Spender" video, it would've been HUGE, I mean it had everything radio loves beat knocked, catchy sample in the back ground, monster guest feature (Jay was still hot as fish grease due to his double dutch approach to the game) song was catchy too...
Had Shawn agreed to do this video, Curtis would've inturn did the video for "Take It To The Top" which was would've been another lay up with the radio and video channels.
He could've threw "Still Got Love" out as 3rd and final single which will dope on its own would've done well from the push and response of the 1st two singles allowing people to pay attention to Free on his own, allowing him to shine dolo. He should've atleast been able to see gold, which would equal Free WINNING.
My Guy Should've Won.