At that point how did you know that? Hadn't seen them.
If he's wanting the same deal, and being a mass murderer before it's necessary, how is Rick not a tyrant?
He was basically saying "We'll save you from that oppresive tyrant, by oppressing you the exact same way!"
No "we'll work together as a community" no "we'll take whatever help you can give" just straight up "give us your shit"
Negan was just bigger and better at it.
Season 6, Episode 11
--At the beginning of the episode, Jesus reveals The Hilltop to the group at Alexandria. He suggests that the two communities can help each other out, noting that Alexandria has a large arsenal, but they lack food. He offers to bring the group to The Hilltop so that the two communities can establish trade.
--At The Hilltop, Gregory and Maggie have a meeting -
Gregory: Where you live - is it as nice as The Hilltop colony?
Maggie: It's just different.
Gregory: How do you feed everyone? Jesus said you had land for gardens, but no crops.
Maggie: We just started planting.
Gregory: Planting what?
Maggie: Cucumbers, tomatoes...
Gregory: Oh, crops? Soy, corn, hemp, sorghum?
Maggie: Garden stuff.
Gregory: But you have guns, so I assume you have a decent weapons cache?
Maggie: It's decent.
Gregory: Your infirmary? Is it stocked?
Maggie: Is yours? We came here hoping to talk trade. Do you have enough here for that?
Gregory: You see what I have here. You see what I've built. Jesus said that your food situation was challenged right now. If you don't keep people fed, it comes apart. Let's speak the common tongue here, huh? You don't have shit. Now, I'm happy to help. I'm a nice guy, but we can't just give things away for free. How's this - since you can't offer much, I'll let your people work here for their share. You'd be a welcome addition to the community - smart, beautiful woman. Getting back to that common tongue, I can tell ya, I can make it worth your while.
Maggie: Let me stop you right there.
Gregory: Listen, honey...
Maggie: Stop coming onto me with calling me "honey." You don't have any ammunition.
Gregory: Who said that?
Maggie: You're low on medication. You need things. We need things.
Gregory: Are you going to give us a bottle of Aspirin and a box of bullets?
Maggie: Our communities can help each other.
Gregory: Thank you, Natalie. It was a good talk.
Maggie: We can help each other.
Gregory: We're doing fine. Are you?
--Ethan and his group return to The Hilltop -
Gregory: Ethan, what happened to everybody else?
Ethan: They're dead.
Gregory: Negan?
Ethan: Yeah.
Gregory: We had a deal.
Hilltop Guy: They said it wasn't enough. Was the drop light?
Gregory: No.
Hilltop Girl: They still have Craig.
Ethan: They said they'd keep him alive - return him to us - if I deliver a message to you.
Gregory: So tell me.
Ethan: I'm sorry. (stabs Gregory)
--Rick tries to restrain Ethan as Rick's group starts fighting with the returned Hilltop group. Ethan gets the best of Rick and puts a knife to his throat. Rick stabs Ethan in the neck and kills him. Everyone looks at Rick in surprise -
Rick: What?
Hilltop Guy: Ethan! You killed him!
Rick: He tried to kill Gregory. Then me.
--Hilltop girl punches Rick. Michonne drops Hilltop girl. Rick pulls out his gun.
Hilltop Guard: Drop it now!
Rick: I don't think I will.
Jesus: Everyone! This is over! It's over! Ethan was our friend, but let's not pretend he was anything more than a coward who attacked us. He did this. And these people stopped him.
Rick: What can I do?
Jesus: Put the gun away. You've done enough.
--Rick puts the gun away.
Jesus: You need to know - that things aren't as simple as they might seem. Just give me some time.
--The next scene -
Jesus: Doctor Carson was able to patch Gregory up. He's in pain, but he'll live.
Michonne: So what happens now?
Jesus: Things like that don't usually happen here, but uh, it's settled.
Rick: We heard the name "Negan." A while back there, Abraham had a run in with his men. Who is he?
Jesus: Negan's the head a group of people he calls "The Saviors." As soon as the walls [of Hilltop] were built, The Saviors showed up. They met with Gregory on behalf of their boss. They made a lot of demands. Even more threats. And they killed one of us. Rory. He was 16 years old. They beat him to death. Right in front of us. They said we needed to understand right off the bat.
Gregory's not exactly good at confrontation. He's not the leader I would have chosen, but he helped make this place what it is, and the people like him.
Maggie: He made the deal.
Jesus: Half of everything. Our supplies, our crops, our livestock - it goes to The Saviors.
Glenn: What do you get in return?
Jesus: They don't attack this place. They don't kill us.
Daryl: Why not just kill them?
Jesus: Most of the people here don't even know how to fight - even if we had ammo.
Rick: Well, how many people does Negan have?
Jesus: We don't know. We've seen groups as big as 20.
Daryl: Hold up. So they show up and kill a kid, and you give them half of everything? These dicks just got a good story. The Boogie Man, he ain't shit.
Jesus: How do you know?
Abraham: A month ago, we took his guys out PDQ. Left them in pieces and puddles.
Daryl: We'll do it. If we go get your men back, kill Negan, take out his boys, will you hook us up? We want food, medicine, and one of them cows.
Rick: Confrontation's never been something we've had trouble with.
Jesus: I'll take it to Gregory.
Rick: They have food. We don't. We don't have enough of anything - except us and what we can do. This is the trade.
Maggie: It's going to cost us something.
Jesus: Gregory's up. He wants to talk - to Maggie. He wants to talk to Maggie.
Glenn: You got this.
Rick: Deanna was right about you [Maggie].
Jesus: Sorry in advance. Gregory can be a real prick.
Maggie: I know.
--
Gregory: Sorry for the gloom. They have me on these antibiotics that have me sensitive to the sunlight. This is agony. It feels like someone is twisting my intestines with a cement mixer.
Maggie: It could have been worse. You're lucky we were here. Jesus told you about our offer?
Gregory: He did. What makes you think that you can do what we haven't done?
Maggie: We've handled people like Negan.
Gregory: How?
Maggie: They're dead. We can get your man back.
Gregory: I don't know if Craig's worth the trouble. I mean it's his brother who did this.
Maggie: He was fighting to save someone he loves. He was afraid.
Gregory: That makes him weak. Frankly, I don't know if I want him back in our gene pool.
Maggie: My dad used to tell me that forgiveness takes more strength than anger.
Gregory: Well, I guess he's a hell of a cook. He makes these amazing baked eggs with green tomatoes.
Maggie: You give us supplies, we'll save Craig and take care of Negan and The Saviors permanently.
Gregory: (laughs) I'm sorry, I find this whole conversation pretty funny. I mean, you barked when I proposed that your people work for our supplies, but now, isn't that exactly what's happening here? See, I had leverage, and I used it. See, it wasn't personal.
Maggie: Yes, we need food and you have it. We're willing to work for it.
Gregory: Then, I'll get supplies for your people.
Maggie: Good.
Gregory: I'll talk to Jesus. He'll make the arrangements. See? This is fun. Exciting.
Maggie: Half.
Gregory: Excuse me?
Maggie: Half of what you have. I saw what happened out there. Negan's expecting more supplies from this place. And more, and more. And if it keeps going like that, pretty soon you won't have anything left. What happens then? Without ammo? Without fighters? You'd be a dead man. So, half of everything you have. Right now. Or the deal's off. You see? I have leverage.
Gregory: Congratulations. You have yourself a deal. You want anything else? Kidney, maybe?
TLDR: That's why Negan was a tyrant and Rick wasn't. Rick and the others didn't show up to The Hilltop, kill a child, and demand half of everything The Hilltop had. Rick and the others at Alexandria were sought out by Jesus so that the two communities could begin trading with each other. Alexandria offered the only services they had in return for the supplies they needed. The Hilltop wasn't strong-armed into the deal with Alexandria. The deal between Hilltop and Alexandria was also meant as a one-time deal, not the constant "we always get half your shit or we kill your people" racket that Negan had going. Rick also didn't hot iron anyone's face to "keep them in line." And, even though it was really messed up to slaughter so many Saviors, he didn't force any of his people to participate in killing those Saviors.