4. They weren’t proactive in locking up youngsters.

The Orioles’ trade of Machado, ultimately, came down to financial limitations. The 26-year-old, four-time All-Star and two-time Gold Glover is expected to command a lucrative contract in free agency this winter, pricing himself out of the Orioles’ range. The club had no choice but to trade him or else let him walk away at the end of the year with nothing but a compensation pick in return.

The situation, though, could’ve been avoided if the Orioles had locked up Machado to an extension several years ago, before his price tag began to skyrocket. Duquette said that the two sides were close to an agreement earlier in Machado’s career but “couldn’t quite get a deal done.” Afterward, the talks went dormant, and it became a foregone conclusion that Machado would wait and test the free-agent waters.

Vice president of baseball operations Brady Anderson admitted at January’s FanFest that the Orioles may have missed their opportunity with Machado.

“Certainly, retrospectively, you think, could we have given him more early on and had him for two or three more years?” Anderson said. “I think the best time might’ve been right after his second knee surgery [in 2014], when maybe he was feeling a little unsure of his own future.”

During the Duquette era, re-signing players before they reach free agency has been rare. Two notable exceptions were Hardy in 2014 and Adam Jones, who signed a six-year extension in May 2012. Otherwise, though, the Orioles tend to let their players reach the open market rather than sign them at a lower cost earlier in their careers. As a result, they’ve often cost themselves millions of dollars or have lost the player in free agency.

There’s little evidence that the Orioles’ passive approach has changed. The club’s next big-name player who’s eligible for free agency is Jonathan Schoop after the 2019 season. Schoop told Dan Connolly of The Athletic that the Orioles haven’t yet approached him about a contract extension.

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