Santino, at least in my opinion, came into the WWE in an interesting way, and at the beginning, he was brought in and was primed to be a star in the WWE.
He won the Intercontinental Championship and got into a feud with Chris Masters shortly after...
Then at Vengeance: Night of Champions, he faced Umaga, who lost from DQ, but then the next night they had a rematch, where we saw Santino lose the title. They utilized him well at the beginning, then it all went downhill from there...
It wasn't all bad then. He got beat down by Stone Cold Steve Austin after Santino bashed his new movie "The Condemned". He then got into a short feud with Jerry Lawler, then went on to tag team with Carlito.
Maria, at the same time, just posed for Playboy magazine, making Santino mad, which led to their breakup. At Wrestlemania, Maria had a "Bunnymania Lumberjack match", where Santino interfered but got knocked down by celebrity guest Snoop Dogg. (WTF #1) The day after Wrestlemania, Maria beat Santino in a match. (WTF #2) This was a low-point in his career, but still isn't the lowest.
He then went on with Carlito to feud with Hardcore Holly and Cody Rhodes over the World Tag Team Titles. During a title match, Roddy Piper distracted Santino, and then they went on to feud with each other. (WTF #3)
Santino Marella did an open challenge and Beth Phoenix defeated him. (WTF #4) Santino then went on to lose to D'Lo Brown. (WTF #5, D'Lo Brown had the feud then left WWE! Good going, WWE)
Then he and Beth Phoenix started dating, and they called themselves Glamarella. They went on to face Kofi Kingston and Mickie James, where Kofi's IC and Mickie's Women's titles were on the line. Beth pinned Mickie James and won the titles for them.
Marella went on to lose against Honky Tonk Man (WTF #6), and later to the Royal Rumble was eliminated by Kane in 1.9 seconds, breaking the previous record. (WTF #7) Phoenix and Marella broke up eventually.
He then went on to win a "Miss Wrestlemania" 25-diva battle royal contest under the gimmick of "Santina Marella", Santino's twin sister. (WTF #8, #9) Then on Raw, he lost the "Miss Wrestlemania" title to Vickie Guerrero, but then later went on to win it back against Vickie and Chavo. Donald Trump, the then GM of Raw, fired Santino. (WTF #10)
Santino lost a 26-man battle royal before Wrestlemania, then began to try to start a tag team with Vladimir Kozlov, who declined. They later faced each other in a dance off, where Vladimir won (the whole dancing thing, WTF #11). Regal and Santino faced off against each other, where Kozlov was the guest referee, and Santino won.
While it seems like there is hope for Santino to turn his career around, I doubt WWE is that smart in doing so.
WWE ruined what could have been one of the best gimmicks in recent history. Santino is a fairly good wrestler, and he can get the crowd going better than a lot of people. He could've been huge, but hey, that's WWE for you.