Jason didn't expect Shane to need something from someone, and it sounded even weirder to Shane that this person had to see him in order to hand over the things Shane required.
He was missing lots of information right now, but the fact that Shane asked him to trust his decision, and that he said 'please' made Jason's stance clear.
Until now, he hadn't done anything great for his masters, who had supported him to their fullest capabilities. As such the least he could do was to trust them.
Since Old Drake's betrayal, Jason had problems trusting other people, but what kind of life would he live if he were to never trust anyone in his entire life again?
That sounded unfavorable and extremely uncomfortable.
Living a life where you can't trust anyone would be annoying and frustrating.