Chris Masters:
Have him go on an undefeated streak with jobbers, and lower carders (Chavo, Croft, Mercury, JTG, Reks, Yoshi, etc ). After several months of this have him challenge IC champion Dolph Ziggler for the IC Title. Vickie Guerro uses her powers to insist if Masters doesn't win the belt he will not receive another shot at the IC Title while Ziggler is champion. Drew McIntyre interfers, getting Dolph DQed but saving his title. It is revealed Drew did this for a WHC shot against champion Chris Jericho (face). Masters, to get revenge, partners up with Jericho to keep McIntyre from winning the title using nefarious means. Jericho, the wily veteran, teams with Masters and since Masters is banned for the IC Title, Jericho and Masters challenge for the Tag Titles and win them, giving Jericho dual titles, and Masters the ability to go to both shows.
Masters wins the RAW MITB (he is a SmackDown! superstar but he entered a RAW qualifying match), and as the RAW MITB holder he challenges the WWE Champion to a match at Summerslam. At Summerslam, Chris Masters faces HHH (heel) for the WWE Title, and in a shocking move wins cleanly, with the Masterlock. Afterwards he and Jericho lose the Tag Team Titles, and is moved to RAW permanently. The partnership continues though, as they are shown being friends at PPV's, Superstars, etc. That all comes to a head though at Elimination Chamber, when Masters turns heel, cheating to retain his title (brass knuckles in his trunks to sneak them into the chamber). Masters loses his title to John Cena at WM 28, and then is drafted to SmackDown! where Jericho tries to be his friend but Masters just wants the WHC Jericho still holds, he is possessed with being champion.. Have them feud for about 6 months (a one off match Masters wins, Jericho wins the rematch, Masters works his way back into contention and constantly is obsessing about getting another match, they finish the feud at Night of Champions in a no holds barred match.
Next challenge: Tyson Kidd