User blog comment:Kaido King of the Beasts/Chapter 864: You've Never Had an Enemy Like Me/@comment-24850639-20170502152326/@comment-24769684-20170502174927

Judge was always destined to fail, to get him out of his smug superior attitude around Sanji and his philosophy that might makes right. Now, his technology and super soldiers that he has held so dear have failed him, and his failure son Sanji is going to be the one to rescue their sorry asses.

Also, he has no real reason to suspect that Big Mom would try to pull anything. His own plan to capture Pudding after the wedding was pretty ballsy from his perspective. He has every reason to believe Big Mom would honor their deal, since she's made plenty of flourishing partnerships through marriage. Should she decide to not honor the deal, she'll have Pudding erase the memories of whomever's present at the wedding, as Pudding said right before her and Sanji's wedding started. Big Mom does not have an air of suspicion around her in this regard to someone like Judge.