Gregory was still laid up in bed, which meant that he couldn't get in the way or complain about anything or just overall be obnoxious in ways that grated on Jesus' nerves in ways he never felt qualified to act on. He was a runner, not a leader, and without someone to replace him, well...

In any case, the people of Alexandria were helping them even though Jesus got their supply truck lost in a lake and hell, even though they were taking supplies and a cow there was a real benefit in it for Hilltop and there's no threat of death or worse behind it - he looked on the bright side really, and tried his best to see the good in people.

He knew they were coming to pick up the cow so he was already out and about when the gates started to open. Which meant that Jesus ended his current conversation with Harlan and wandered over, gait easy but not taking his time. He was waiting rather patiently when the delivery truck pulled into place, gates still in the process of shutting behind them.

The smile he wore was, of course, that infuriating and knowing thing he always wore but it was pleasant enough and at least he wasn't wearing the damn hat today. So soon as either Maggie or Daryl alighted from the truck, it'd spread a little wider. "Glad you could make it."

If Gregory said it, it would have sounded like a petulant insult. From Jesus, it sounded genuine.