You're looking too much at the roadblock itself instead of what was being said by Negan. He's telling Rick I am in control. You're not as big and badass as you think. You'll go where I want. Do what I want. Each roadblock was bigger or more elaborate than the last, telling Rick I have a lot of resources. Then when Rick finally ends up where Negan wants him, he castrates him. In Rick's words, they f'd with the wrong people.
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