Viewers can probably count on one hand the number of times that Rick Grimes has really and truly smiled on The Walking Dead, so it may have come as a surprise for many to not only see Rick grinning, but doing so while being surrounded — and outnumbered — by an angry mob of strangers holding guns. Why would Rick express so much happiness when, from the perspective of the other Alexandrians, it appeared as though Rick could be killed?
Here’s the best explanation I could come up with: In the opening minutes of tonight’s midseason premiere, “Rock and the Road,” Father Gabriel took all the food from the Alexandria pantry, as well as a few other items of interest, packed them in his car, and — for mysterious reasons — drove away in the middle of the night. Late in the episode, when Rick, Aaron, and the others returned from their visits to both The Hilltop and The Kingdom, they were informed of Gabriel’s getaway.
While many in Alexandra assumed that Gabriel took the food and ran away because of the pressure he felt from Negan and the Saviors, Rick understood that Gabriel would never so such a thing. Though they were once at odds — and Gabriel had even sold Rick out, at one point — in more recent times, Gabriel has become one of Rick’s most trusted friends. The tide turned when the herd of zombies crashed into Alexandra, and Gabriel protected baby Judith as they navigated themselves through the walkers while covered in zombie guts. Since then, Gabriel has been left in charge of Alexandria in Rick’s absences, as was the case on that ill-fated night when Abraham and Glenn were killed. Gabriel also wisely staged Maggie’s fake grave to convince Negan that Maggie had died.
In other words, Gabriel wouldn’t betray Rick. Rick knows that, so he went in search of evidence proving that Gabriel didn’t simply runaway. Inside the pantry, Rick found Gabriel’s Bible — specifically left open to send a message to Rick — and a notebook with the word ‘BOAT’ written on the last page. Rick correctly surmised that the BOAT Gabriel was referring to was the houseboat that Rick and Aaron paddled a canoe across a zombie-infested pond to get to in order to retrieve supplies for Negan.
“How would he know we were out there?” Aaron asked Rick. “I don’t know,” Rick replied, but he understood that somehow Gabriel did know about their trip to the boat.
How did Gabriel know? Remember in episode 7, when Gabriel and Spencer got into a fight in Spencer’s car? The fight was about Rick. Gabriel believes Rick is an inspiring leader who brings everyone together, and Spencer hoped that Rick would die. “What you’re saying doesn’t make you a sinner,” Gabriel said. “But it does make you a tremendous sh*t.” Afterwards, Gabriel asked to get out of the car and walk back to Alexandria.
This, I believe, is when Gabriel likely spotted Aaron and Rick headed toward the boat. In fact, Gabriel might have even met someone in the new community, which we’ll call the Junkyard Gang. Either that, or Gabriel met and talked with the boot-wearing spy from the Junkyard Gang one night while she was spying, and Gabriel was on lookout.
In either respect, Gabriel knew about the boat, and he also knew about the Junkyard Gang. Gabriel took all the food from the pantry as part of a designed plan to lure Rick, Aaron, and a few others back out to the boat. Why? Because Gabriel knew that the Junkyard Gang would supply Rick with the army he needs to take on Negan and the Saviors.
So why was Rick smiling in the final seconds of the episode? Because he realized, as he was being surrounded by the Junkyard Gang, exactly what Gabriel had planned: Gabriel was introducing Rick to his army of red shirts. They will give him the numbers he needs to defeat Negan. When Rick saw a 100 people surround him, he understood then that there would be a way forward, a way to beat Negan, and these people holding guns to his head would be his key to victory.