At the end of the day, it's Boras' job to get his players as much money as possible. That has worked out in some cases, and not with others.
Hopefully the "winning" environment here will encourage players like Gunnar and Adley to sign extensions. I'd love to hear that the Orioles signed Henderson to a 10-year contract because he is a franchise guy. Adley is a catcher so that scares me more, but I'd be willing to extend him until he's 31 or 32.
Gunnar though is the key and I think the Orioles know this. He's one of the best players in the league, he's fast, athletic, and barring a serious injury, there is no doubt he's going to be one of the best players in the league for a long, long time.