I remember the older brother saying something to young Ward that basically he'd throw him into the well if he disobeyed him... Although, I think that was when Ward was debating whether to pull Thomas back up, not how Thomas got into that well.
Well, all the Hydra members are basically true believers as far as I can tell. The SHIELD members seemed not to be, so when SHIELD dissolved, there were probably more Hydra agents willing to keep fighting than SHIELD agents.