According to Boras, there is mutual interest in getting an extension done, and as Connolly notes, it is somewhat rare for the Southern Californian to travel and visit with a team in-season.
It's possible that Boras is not only coming to Baltimore to discuss Wieters. Designated hitter Pedro Alvarez and closer Zach Britton, both Orioles impending free agents, are Boras clients.
As for the other side of operations, Orioles Executive Vice President Dan Duquette often shies away from making extensions during the regular season, but did sign Adam Jones and J.J. Hardy to long-term deals during play, in 2012 and 2014, respectively.
The 30-year-old Wieters is currently signed through 2016 on a one-year, $15.8 million deal completed last offseason. Wieters was among the first round of players to accept a qualifying offer, but, in 2016, the results on the field have been subpar as compared to his standards in past years.
The most likely comparison for a new Wieters deal could be the five-year, $75 million deal signed by Yadier Molina in 2012. Molina was a year younger than Wieters, and definitely more highly touted, but signed the deal with seven years and 123 days of service time. Wieters will begin 2017 with approximately seven years and 129 days of service time.
Perhaps a more likely scenario for Wieters, considering his injury history, would be a four-year, $60 million deal, staying in the same annual average value range as the Molina deal but limiting the years the Orioles will have to commit.
This season, Wieters is hitting .243/.299/.402 with 14 home runs and 60 runs batted in over 110 games (412 PA). According to FanGraphs, he has been worth 1.2 Wins Above Replacement.