The real problem with Wil's plan is that he didn't think it through. He needed to make his ruse more complete, and if he had, it might have worked. They bungle it immediately, though, by failing to jump out of the cab. "We're going to get out like we're going," Tara says to the cabbie as Wil climbs out. "You need to back up and turn this bad boy around." They casually get out of the cab, and that's why Chris and Alex aren't fooled. "Get back on the bridge, get back on the bridge," Alex says. "Yeah, they're fakin' it up, man," Chris adds. So in a sense, this plan "worked," in that Boston stopped following Wil and Tara. But in the sense that Wil intended to fool Boston into thinking this was the fort, it didn't work. I think that, for one thing, Chris and Alex are thinking about the Teeth and realizing that they can't screw around with Wil all day.
Boston stops to ask directions to East Fort Baker, as Wil and Tara take off for the fort on foot. Huh? What seems to happen here is that from where they were, Boston gets directions and gets a cab to Fort Baker, whereas Wil and Tara start running up a big hill, because Wil thinks you can just run straight to the Fort. Wil quickly realizes that this is not the case. Tara yells that he's an idiot. Again. He screams for her to shut up. Again.
(I don't really remember when it was, but I slid my chair over to lawtalkin' guy at some point during the later stretches of the episode and said into his ear, "Are they going to win? Seriously, are they going to win? They are, aren't they? They're going to win." He was unable to make me any promises one way or the other. ["Across the room at around the same time, I began praying aloud that Bruckheimer just wanted us to think they were going to win, and that they therefore would not. Which worked out for me, but it was a dicey few minutes." -- Sars])
Boston asks directions from a guy in a truck, which seems to be one of their primary race strategies. Meanwhile, in the Taraweasel cab, she's berating him, which we know is one of her primary race strategies. "Was that really a smart move?" she snots. Well, actually...sort of. They fight some more. "You're stupid, though," she says to him. "I mean, I hate to say it, Wil, but why would you put us at a dead end?" First of all, she doesn't hate to say that he's stupid. She loves to say that he's stupid. She says it all the time. If she hated saying it, she would just not say it. Second, it wasn't THAT bad of a move. She was the one telling him constantly that there was no way they could win if it came down to a footrace, so he tried to find a way to separate the cabs. I mean, the fake-out thing was stupid, but I'm not sure it was all that wrong for him to try to do something.