In the Orioles’ season-ending press conference with media (including MASNsports.com’s Roch Kubatko) earlier this week, baseball operations executive VP Dan Duquette commented on the possibility of the club exploring extensions with several players, saying “I’m sure we’ll have time to take a look at that” during the offseason.

All of those players have done a great job for us,” Duquette said, referring to Manny Machado, Chris Tillman and Jonathan Schoop.  “We have explored extensions in the past, in fact a couple times each, with Tillman and Machado. We haven’t approached Jonathan Schoop on a long-term basis yet, but I’m sure we’ll have time to do that when it’s appropriate.”

As Duquette noted, this isn’t the first time the O’s have looked into extending its superstar third baseman or its staff ace.  FanRag Sports’ Jon Heyman reported in June that Machado and the Orioles had come close to a seven-year extension at some point in recent years, while the club negotiated with Tillman about a long-term deal prior to the 2015 season.

A Machado extension, of course, would almost certainly be one of the largest deals in baseball history.  Machado has generated more fWAR than all but three other players in baseball over the last two seasons, thanks to his combination of both elite third base defense and outstanding hitting.  At just 24 years of age, Machado will only be 26 when he hits free agency after the 2018 season, so the Orioles would need to pay well in excess of $200MM in order to lock up the young star into his free agent seasons.  Extending Machado would break new financial ground for the O’s, though Baltimore has shown it is willing to spend big to extend or retain key position players like Adam Jones or Chris Davis.

Tillman is the most immediate concern since he can hit the open market after the 2017 season, though his price tag is less clear.  He rebounded from a disappointing 2015 season to post a 3.77 ERA, 2.12 K/BB rate and 7.3 K/9 over 172 innings this year, though as per advanced metrics, there actually wasn’t much of a gap between the righty’s performance over the last two years.  Tillman has produced between 1.8 and 2.4 fWAR in each of the last four seasons and averaged 190 innings per year in that span, though the Orioles are notoriously cautious (some could say over-cautious) when it comes to committing to pitchers in long-term deals.  It could be that the Orioles would be more comfortable spending money on a pitcher they’re already quite familiar with, especially given that the club is already in such need of rotation help.

Schoop will be eligible for arbitration for the first time this winter, so the Orioles aren’t necessarily in any rush to extend the second baseman.  Schoop, who turns 25 next week, hit a career-high 25 homers but was a below-average (97 wRC+) offensive performer overall thanks to a .267/.298/.454 slash line over 647 plate appearances.  Between Schoop’s high strikeout totals and lack of OBP, there could still be some question if he is indeed a long-term piece for the Orioles, though obviously there’s still room for growth for such a young player.

Duquette was also asked about the possibility of extending star closer Zach Britton, and Duquette merely responded that Britton is still two years away from free agency.  Extending Britton now would be the definition of a buy-high move given that he is coming off one of the best seasons from any closer in baseball history, though an extension would also give Baltimore some cost certainty over Britton’s rising price tag.  He is due a major raise from his 2016 salary of $6.75MM,  and he still has two arb years left thanks to his Super Two designation.  Committing huge dollars to any reliever can be a roll of the dice, so the Orioles could be willing to simply go year-to-year with Britton.

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