Housepets!

Like, seriously, Mr Steward is clearly not someone Keene can trust in continuing Henry Milton's undertaking. He's probably a plant from one of Henry's anti-reconciliation enemies.

Does anyone have any thoughts on this?

I very much agree
Though I do wonder if he has someone specific he gives information to, or if he's trying to dig up enough dirt to get something out of it

Keene even says straight up that he doesn't trust Mr Steward at the beginning of that arc in Call No Waiting.

Here's a question:
Pete wasn't really a villain, just a jerk... So... Is whoever Steward is working for a real villain? Are they against human-animal-reconciliation, or just keeping tabs on the Miltons? Are they actively malevolent, perhaps because they want to keep their place in the status quo, or just afraid of the ramifications of Henry and Keene's undertaking? So far he hasn't stopped Keene from doing things, like taking on the wolves or raiding the temple, but that doesn't mean he's not just laying low and spying...

It's also entirely possible that he's just a concerned citizen with no other motives, or that he's from a group which is pro-reconciliation and is vetting Keene as a potential ally...

my money would be on anti-reconciliation. Keeping people divided and factionalized is often a good way to sell products (see: Console wars) which would mean there is a possibility of large companies having a financial stake in the status quo that they would be more than willing to defend.

we see it all the time with issues irl.

I think that there's more to him then can be seen, but I don't think he's a spy or sent there to undermind Keene's plans. I think it's more simple, he just took Keene to be a typical rich brat, till he realized there was more to him. Or, you could be right and he could be a spy, but I wouldn't hold my breath waiting for Rick to show us just what the deal is, not yet anyway. There are so many stories to tell.

I'm not sure... But did anyone try to find connections between Daisy (She got the prize) and Mr Steward?

As I just now saw this topic, I couldn't help but wonder, with all that's been happening recently in the comic, maybe this all has something to do with Mr. Steward as well! Maybe Steward is trying to get Keene out of the way and he sabotaged the car! It would kinda explain why it's all cut up because businessmen like Steward wouldn't know how to correctly sabotage a car so they'd have to resort to destroying everything!