Sam's got a friend in prison named Juan who's run afoul of a gangleader named Cruz and thus has a day to live. Sam's Plan A, to break into the prison, is aborted on the launch pad because the gang members will recognize him. Plan B, in which Michael goes in instead and runs interference for Juan long enough to keep him alive until the guards come to the rescue, proves equally flawed when the guards turn out to be on the take. Plan C, to bust Juan out with a week left on his sentence, goes afoul when Cruz breaks Juan's leg so he can't run. So as usual it's Plan D, in which Cruz is smuggled out, only to be immediately recaptured. And presumably killed by other gang members.
In long-term arc news, Michael gets his meeting with Simon, who directs him to a stash of materials hidden in a cemetery plot. Since Michael's in stir for most of the episode, it's left to Fi to dig it up and disarm the booby trap, with assists from Sam and Madeline. The big prize? A recording of a phone call in 2007, when Vaughn can be heard discussing Michael's then-impending burn notice. Now that Michael knows that Vaughn isn't the Johnny-come-lately in Michael's personal drama that he's always claimed to be, Simon feels ready to tell Michael that the shadowy figure they're after is actually a famous technology CEO, who's starting all these wars so he can build the materials to supply them. And if Michael gives that man the Bible, it'll be the end for Vaughn and his whole organization. Michael tells Vaughn what he learned from Simon -- but not everything he learned from Simon.
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Michael is staring all intensely at Simon's dossier, whose guts he has taped all over the wall of his loft. For what it's worth, it seems Simon was quite the track star in his youth, until he blew a knee. Fi enters to tempt him with a trip to the shooting range (not a euphemism, I don't think), but Michael informs her that Vaughn is bringing Simon back to Miami today, and Michael's hoping to find out what it all means -- the Bible, Simon's shadowy employers, the works. But since I just found out today that there are two episodes left in the season after this one, I'm not holding my breath.
Michael drives up to the kind of house that's usually occupied by drug lords on this show, only in this case the heavily armed guards aren't even bothering to try to blend in by wearing Hawaiian shirts. Vaughn walks out and grins at Michael, "Nice digs, huh, buddy?" The subtitles remind us that he is "Vaughn -- Michael's Buddy." Michael wants to talk to Simon alone, but Vaughn warns that in the months since the Season Three finale, all they've learned about Simon is his high pain threshold. Michael says that's not the approach he plans to use.
Inside the house, Michel finds a scruffy, bloody Simon sitting in an armchair in a solarium with a security camera overhead, with his hands cuffed together in his lap. Which of course makes him as dangerous as a fluffy bunny with social anxiety and a spinal cord injury. Simon tells Michael he's been dreaming of this for months, and Michael returns the compliment, sort of, as the subtitles remind us of "Simon -- Rogue Operative, Walking Nightmare." Michael tells Simon about the Bible he stole after someone else tried and failed to steal it first. Simon holds up his cuffed hands in what looks like prayer while Michael VOs that handcuffs are subject to metal fatigue just like anything else, if you give someone long enough to work on it. But surely they've been changing Simon's handcuffs? Nope; as Simon quotes his favorite verse about the truth setting you free, he breaks the handcuffs, leaps from the chair (no leg irons?!) and drags Michael crashing through the second-floor window. Fortunately for both of them, they land on a preternaturally sturdy chaise longue. Here, out of range of any surveillance devices and with 30 seconds before any guards arrive, Simon gives Michael a gift even as the latter grapples underneath him: "Cemetery, Third and Grand. Go to plot 837, there's some keepsakes of mine in there, including an audiotape labeled Berlin 2007." Simon adds that he'll talk to Michael about the Bible after Michael hears what's on it. Then Simon starts fighting harder, drawing blood to make it look good for the guards who are rushing up to take Simon away. "Did you learn anything?" Vaughn asks after checking that Michael's okay. Michael answers in the affirmative: "You should replace his handcuffs more often." Yeah, no shit. And maybe accessorize them with a straitjacket.