If the Orioles once had a frosty relationship with agent Scott Boras, it has certainly thawed in the last few years, which is important now.
Two major Boras clients, Chris Davis and Matt Wieters, are Orioles who are now two years from free agency. It is a critical time for the club to determine if they can re-sign one or both, or if the best move would be to trade one or both. There have already been rumors that the O's haven't gotten very far in their pursuit of a long-term deal with Wieters, and now we've seen reports that the club is willing to trade him.
Jim Duquette has experience dealing with Boras. The former front office executive for the Mets and Orioles is a baseball analyst for MLB Network Radio on Sirius XM Radio and works on O's coverage in Baltimore on 105.7 the Fan.
He was part of the thaw between Boras and the Orioles when Duquette and Mike Flanagan drafted Wieters with the fifth pick in 2007.
Duquette said that Boras' trend of taking players to free agency means the O's have to be open to the possibility of dealing one or both players.
"His inclination is not to do something like that unless it is a pretty large deal," Duquette said. "It is on the players to almost step up and tell him, 'Hey, I want to stay here and I'm not looking for every last dollar.' One of those two, or both, are going to have to step up and direct Scott in what they want to do.
"You have to be open-minded to trading them if you don't think you can re-sign them. That is a critical question to be answered."
But what kind of deal would it take to get one or both to sign a contract extension?
"The hard part about Davis is he's coming off a huge, MVP-like season," Duquette said. "In your mind, you are wondering, 'Can he do that again?' If he does, you are talking a stratosphere that very few players would go. That is the problem if you wait. It would be tough to get him with one year to go before free agency.
"Deals like that become very difficult to do. He had one really, really good year. Yeah, he had a good year two years ago, but now he took it to another level. If that is your starting point, you are talking into $100 million and only the Orioles know if that's a doable number."
I asked Duquette if a five-year, $100 million deal for Davis is a place to start in potential contract negotiations.
"That should be enough to get your attention," he said. "You'd be talking about a record-breaking deal for the organization. That is a reasonable number, but before you even present that, you have to have a feeling that you would be close and I'm not sure Boras would sign something that close (to free agency). But if you presented that to Chris Davis, boy, he'd have to think really hard to turn down that kind of money."
Duquette pointed out that not every Boras client goes to free agency. The Los Angeles Angels signed pitcher Jered Weaver to a five-year deal worth $85 million in August 2011. Weaver would have been a free agent after the 2012 season. Some think he left a lot of money on the table.
Duquette does agree there is quite a difference in trading a player with two years left before free agency rather than waiting until there is just one year remaining.
"Yeah, it can be," he said. "Tampa is probably the industry expert when it comes to selling their players at the ideal time. Look at what they did with (Matt) Garza and (James) Shields and now what they are doing with (David) Price. Each one was moved with two years left. This is the critical time to try to sign or trade them. Not that you can't deal them next year though."