By the way, I've been avoiding spoilers this entire season, and so would not have had the faintest clue that twist was coming had it not been for the appearance of the actor's name in the opening credits scroll following the title card, so you might choose to keep that little detail in mind the next time you want to fake out the audience, Kripke. Just a suggestion.
Sidewalk. Aftermath. Sam seethes, Dean gapes, The Trickster gloats, and all you need to know is this: the time loop's not about killing Dean over and over and over again as some sort of twisted retribution for the events of last season, no matter how much enjoyment The Trickster's been receiving in doing so. No, the entire point of this exercise is to teach Darling Sammy a lesson. "How long will it take you to realize?" The Trickster smirks in Sam's face. "You can't save your brother, no matter what!" Dean looks deeply uncomfortable. Sam, on the other hand, looks psychotic, and is about to jam that stake through Richard Speight's neck when The Trickster offers a deal: If Sam lets him go, The Trickster will send both Winchesters forward into Wednesday, no harm, no foul. Sam considers this for all of a second before hissing, "Nah, it's easier to just kill you." "Can't have that!" The Trickster grins, and he snaps his fingers.
Huey Lewis And The News choad their way through "Back In Time" as Sam snaps open his eyes and bolts upright in bed. Dean, brushing his teeth at the sink, makes disparaging remarks regarding the station's choice in music this morning, but Sam's too overjoyed to discover they've finally reached Wednesday and declares Huey Lewis And The News to be The Best Band Ever!, so we know something's not quite right with Sam. The Ginormotron hastily pulls on a shirt while quizzing Dean about the previous day's events, but all Dean remembers is their run-in with The Trickster. That's good enough for Sam, who scrambles out of bed to sling all of their crap into duffel bags, because they're leaving town, pronto. "No breakfast?" Dean protests. Wah-wah-waaaaaah.
Impala. Dean's transferring supplies from Metallicar's bottomless trunk into a bag when Deadbeat Cal comes on little cat feet with a gun to relieve Dean of his wallet. Instead of, oh, handing it over immediately, Dim Dean decides to talk his way out of the situation, and the camera cuts back up to the room so we can get an earful of the expected gunshot with Sam. Down in the parking lot, Cal's scampering away while Dying Dim Dean bleeds out all over the asphalt, and... "GOOOOOOOOOOOOOOORE" Oh, Raoul, really? "Whatever do you mean?! Is there not a delicious amount of tasty GOOOOOOOOOOOOOOORE on the television screen at this very moment!?" There's a delicious amount of something, all right, but clearly it's red-dyed Karo Syrup that's squirting out from Jensen Ackles's olive drab t-shirt at the moment. I mean, come on -- look at that! It's making a tiny little perfectly arched stream from what's clearly the business end of a hose they ran up beneath his clothes, for Christ's sake. "Oh, pooh! You simply have to ruin all of my fun, don't you!" Don't blame me, dude. I'm not the one who rigged that shit up. "Rats!"
And so, long story short, the Very Touching Moment when Darling Sammy races to Dead Dean's side to plead with whomever is listening that this wasn't supposed to happen today gets ruined by an errant blood bag, or whatever, and as the camera cranes up from the Pietà-like tableau in the parking lot below, your heartless recapper and his cold-blooded friend enter the next CHOMP!-less commercial break entirely unmoved.