Would have been incredibly simple to get him that homerun

Yes Gil said he'd be watching to see if the pitcher goes easy on Bobby, but you could easily coordinate so that bobby knows what one specific pitch in the AB is going to be. If you tell a hitter of his caliber exactly what pitch is coming next and the location, chances are good he'd crush it.

Or just give him a very corked bat so that any contact will just make the ball fly of the bat.