The Trickster knew that something was off when he met those Winchester brothers back in '06. That tall one was a force to be reckoned with (well not to him anyway). Loki watched this one particularly carefully of the two.

What he wasn't expecting was for a bond to form between them.

You may be wondering why Loki has formed a bond usually reserved for Angel's. Well if you are, you really shouldn't be reading this story. Come back when you understand. But if you really don't want to go away (I can understand why I'm awesome like that!( then simply know that Loki is really the Archangel Gabriel. On top of that he is the only Archangel to not have an Angel mate. Which he felt was a kick in the teeth.

Anyway, he really wasn't expecting that bond to form, after all he had given up all hope on anything angelic when he had left heaven, which included mates. Then to be stood here, in an abandoned theatre reeking havoc on the Winchesters, and felt that bond form, it was quite a shock to the system.

A shock to the system that caused a huge bout of homesickness.

And that was when he faked his death.

Later, at the Mystery Spot, Gabriel was really playing games with Sam. He wanted to tell the human about the bond (that had grown and grown on his side since it's initial forming back in '06. It was only a year but the bond was already so strong that it was becoming cumbersome. Gabriel couldn't take it. He needed an outlet of some kind, so he messed with Sam.

Sam, for his part, was beginning to feel something on his side of the bond. A little twinge of sympathy towards the renegade Angel (that would later bloom into something much more).

Gabriel couldn't deny Sam of his wish to be freed from the time loop, so he sent him forward onto Wednesday, which was really quite a surprise to Sam. He was celebrating the fact Dean was no longer going to die on a repeating cycle of the same Tuesday over and over (ironic that Sam's nightmare of a continuous Tuesday whilst Cas's favourite heaven was a continuous Tuesday afternoon). But, he was also on edge that Dean would die and this time it would be real.

Gabriel was still messing with him. It was Wednesday, but that didn't mean he couldn't kill Dean. He did kill Dean and left Sam to deal with this for several months (which he spent tracking the Trickster/Angel down). When Sam found him, again, he couldn't deny the younger Winchester his wishes so he sent him "Back in Time" (Hence the song that had been playing on the Radio that original Wednesday morning, it was always his intention to send Sam back).

Gabriel knew he was in deep when that happened, but he didn't know how deep it would go.

When Sam and Dean learnt who he really was, Gabriel felt he needed to give them what they wanted, or rather give Sam what he wanted. Which, of course, meant that the archangel would try (and ultimately fail) to kill his older brother.

Gabriel knew he was going to die. He knew deep down that he was always going to die.

And just as Lucifer ran the angel blade through him he sent a silent prayer to his father for Sam to be alright.

Gabriel lay there in that Motel, his wings burnt into the ground around him.

Sam knew something was wrong. He knew it deep in his heart. He just wasn't sure what it was.