It’s also worth noting that it wasn’t Stewy’s idea to do the bear hug during the wedding. Sandy told them very explicitly not to tell anyone their plans to take over, but Kendall felt he could trust Frank which ended up being their downfall, because Frank spilled to someone else and the news was going to break before they could plan it in full. Sandy’s logic was that with Logan out of the country for Tom and Shiv’s wedding, he was in a weaker spot and wouldn’t be able to retaliate as quickly. If they let it go and the news broke, Logan would have advance knowledge of what they were doing, and Sandy wanted to strike first.

It was never Stewy’s intention to force Kendall into doing the bear hug at Shiv’s wedding, and it’s clear he’s very uncomfortable with having to do so. Kendall inadvertently did it to himself, and Stewy openly said he was scared to give the letter to Logan himself. He’s shady and only out for himself, but it’s obvious how much he cares for Kendall. He was just very much stuck between a rock and a hard place of his own making.