The first step in deciding whether to extend a certain player is whether or not the team truly needs them beyond their controllable years. In other words, can they be replaced internally in the future? Wieters and Davis are each two years away from reaching free agency.
With Wieters, the Orioles' catching depth is actually quite impressive. Steve Clevenger
has hit the ball effectively everywhere he's been. Currently at Norfolk, Johnny Monell, Caleb Joseph, and Brian Ward
project to be complementary catchers. Michael Ohlman
is slated to start for the Baysox, and he could be a real solution to Wieters' future absence. Let's not forget the four catchers drafted within the first ten rounds.
As for Davis, there is only one legitimate first base prospect in the minors, and that is Christian Walker. He quietly had a very impressive year at three different levels, and is ranked as the seventh best first base prospect in baseball. Positives aside, it wouldn't be wise to count on Walker as Davis' predecessor. At this point, it sure seems like Baltimore will defintely need Davis more than they will need Wieters after the 2015 season. Therefore, if I were DD, I would focus on extending Davis, and ignore Wieters for now.
The second step would be to determine when to sign the extension. Teams would want to do this when the player's "value" is low. Now, I don't think Chris Davis' value will ever be that low, but at least know that his value will never reach the point that it is at now. Therefore, signing Davis to an extension now, would be paying for the 2013 Chris Davis. We all know Davis won't repeat what he did in 2013. So, let's wait a year for his value to diminish. Steamer and Oliver both predict Davis to be somewhere in between his 2012 and 2013 seasons. That's a reasonable expectation. I would gladly sign Chris Davis to an extension, if the Orioles are paying him like a .900 OPS
The third step would be to negotiate the deal. Joey Votto signed a ten year/$225MM extension at the age of 28 before the 2012 season. Going off of that, I would sign Davis to a seven year(plus the one year of arbitration left, because in this scenario, the Orioles are signing him to an extension after the 2014 season), $152MM. If Davis is unwilling to meet that standard, someone will gladly take one of the best first basemen in the game for the next year.