Jackson is the prize here. And the Orioles would love to have him. In fact, I’ve been told the club would consider a four-year deal for Jackson (something the Orioles and/or EVP Dan Duquette wouldn’t usually do for free agent pitchers) given the fact he is only 28. So, yes, they have interest in Jackson.
What it comes down to is money – and I think we have seen that Boras has a way of getting top dollar for his top free agents.
Given that, and the interest that is reportedly out there for Jackson – the Boston Red Sox, for instance – Jackson to the Orioles is a long shot. Not of the Fielder-variety, snowball-chance-in-July-in-Camden-Yards long shot, of course. But still somewhat unlikely.
Damon is also unlikely. I’ve been told the Orioles just aren’t motivated to pursue him right now. Especially with another potential DH, Wilson Betemit, entering the fold. So you can pretty much cross him off the Orioles’ list unless he still has his thumb out in mid-February.
Truthfully, the Orioles rarely pick up a Boras’ free agent: Michael Gonzalez was the last one, during the 2009 offseason.
But that doesn’t mean the Orioles can avoid dealing with the sport’s ultimate deal-maker. In fact, some of the most important members of the Orioles’ 40-man roster are Boras clients: Matt Wieters, Zach Britton, Jake Arrieta and Chris Davis. So are Taylor Teagarden and Josh Bell and Orioles farmhand Jason Esposito.
Dan Duquette doesn’t appear to have any problem dealing with Boras – it was Duquette, for instance, that brought Boras’ client Damon to the Red Sox and who traded for Boras clients’ Jason Varitek and Derek Lowe.
That’s a good thing.
Because, frankly, if you want to build your team with baseball’s best players, you are eventually going to end up dealing with The Boras Corporation.
One final thing about Boras and the Orioles: His group is the last one to beat the Orioles in arbitration – when Ben McDonald won in 1995. He’s also the last agent to lose to the team in arbitration, when Rodrigo Lopez lost before the 2006 season.
The three remaining Orioles facing arbitration – Adam Jones, Jeremy Guthrie and Brad Bergesen – are not represented by Boras (Guthrie was, but switched to CAA several years ago).