The predicament the Orioles currently face – forced to ponder whether to trade franchise cornerstone Manny Machado one season before he is slated for free agency – should serve as a cautionary tale about the team’s lethargic approach in keeping their best players in orange and black long term. Machado might not be the best example to use because a star like him doesn’t come around very often, and several offseasons ago it became likely that Machado would eventually challenge the record $325 million commitment made to Giancarlo Stanton because of his quickly rising star and the fact that he would reach free agency at age 26. And maybe the Orioles were resigned then that they wouldn’t be able to keep Machado after the 2018 season, or that fiscally speaking, giving him a 10-year deal isn’t a prudent move for the franchise. And maybe that’s why the club never engaged Machado in any real extension discussion over the last three years. But if they knew that, they also should have had a plan regarding the future. If they weren’t going to build a franchise around Machado, then who should they build around? They’ve had time to make a blueprint. And now, any discussions about the post-Manny Orioles should focus around the consideration for giving his buddy, second baseman Jonathan Schoop, a long-term extension. The Orioles will likely attempt to engage Schoop next month when the arbitration process gets going, but according to sources, it’s been baffling how little dialogue there’s been about extending Schoop, especially as the Orioles consider saying goodbye to their best and most popular player in Machado. Even though Schoop still has two years remaining before reaching free agency, the window to sign him to a long-term deal is shrinking. Coming off the best season of his career in which he set career highs in nearly every offensive category, Schoop is slated to receive a significant raise, projected to make $9.1 million next year in his second year of arbitration eligibility. That’s more than double what he made last season ($3.475 million). Schoop also participated in a unique agreement with Fantex in which he received an up-front payment of $4.91 million last year in exchange for 10 percent of his future earnings. Schoop is beginning to make lots of money, as Machado did before him – Machado is slated to make $17.3 million in 2018 -- and like most successful players do during their arbitration process. And also like Machado, the more success Schoop sees, the less reason he has to engage in any long-term discussion.