Manny Machado has been the Orioles’ best position player since Cal Ripken Jr. (AP Photo/Patrick Semansky)

In one dizzying 72-hour stretch leading up to the 2000 Major League Baseball trade deadline, the Baltimore Orioles, with the second-highest payroll and second-worst record in the American League, traded six popular veteran players — Mike Bordick, Harold Baines, Charles Johnson, Mike Timlin, B.J. Surhoff and Will Clark — for an assortment of prospects and spare parts that, with a few years’ perspective, could be distilled down to what it essentially amounted to: Melvin Mora, a two-time all-star for the mid-2000s Orioles, and a bag of balls.

Despite posting losing records for the following 11 straight seasons, Orioles owner Peter Angelos never again approved such a full-scale, midseason sell-off, clinging to the fantasy of fielding competitive teams for the entertainment of his team’s fans, even as those teams crashed every summer — an average of 69 wins from 2001 to 2011 — and attendance at Camden Yards fell to record lows.

But here, in the midsummer of 2017, with the Orioles floundering at 46-49 and on the edge of wild-card contention entering the weekend — their up-and-down season epitomized over the past week by three straight losses to the Cubs and four straight wins over the Rangers — they are willing to downsize their roster again, with certain limitations this time.

Having gained Angelos’s approval, and barring a sudden change in plans, Orioles General Manager Dan Duquette is prepared to deal from his surplus of valued relievers, including Zach Britton, Brad Brach and Darren O’Day, with catcher Welington Castillo and outfielder Seth Smith perhaps also in play. The issue this time around is whether that strategy goes far enough.

The big question is whether it’s also time to part with Manny Machado.

Much has changed about the Orioles’ landscape since the infamous 2000 fire sale. They no longer field top-five-in-the-game payrolls or draw 3 million-plus fans annually. They are coming off a stretch of three playoff appearances in a five-year stretch and the franchise’s longest stretch of .500-or-better seasons since the mid-’80s, but with annual attendances that consistently rank in the bottom half of the game.

They have also seen a series of aggressive, prospects-for-veterans trades backfire on them in the past four Julys, costing them young pitchers Jake Arrieta (2013), Eduardo Rodriguez (2014), Zach Davies (2015) and Ariel Miranda (2016) — all of whom went on to varying degrees of success with their new teams, while the veterans the Orioles received in return failed to push them into the World Series.

This is where the Orioles are in July 2017: still three games out of a wild card entering the weekend, with three other teams ahead of them, while fielding their oldest roster in almost a decade, and in possession of a farm system rated among the worst in baseball. The Rangers series, featuring one dazzling pass through the Orioles’ rotation, was a mirage: The Orioles don’t have the starting pitching to contend for two more months, let alone compete in October. And to further decimate their stock of prospects to chase a fantasy would only do more damage.

If you’ll recall, the prevailing wisdom regarding the Orioles at season’s start was that they had a two-year window — this season and next — to win a title before Britton, Machado and Adam Jones reach free agency. But that wisdom has been called into question over this season’s first four months.

The argument for holding onto Machado, their third baseman and franchise cornerstone and arguably their best position player since Cal Ripken Jr., is a compelling one: Add a few additional pieces this winter and take one last shot with a team constructed around Machado in 2018. If signing him to a long-term extension — an unlikely proposition given a price tag expected to approach if not exceed $400 million — fails to pan out, and the Orioles drop out of contention by next July, they can always deal him then. This appears to be the approach favored by Angelos, who after all is 87 years old and never inclined to throw away years even as a younger man.

But the more realistic view of the Orioles is that the championship window, rather than being open through next season, is already closed, and at this point, Machado is a luxury they no longer need — unless you are someone to whom the difference between 80 wins and 85 wins in 2018 truly matters. The Boston Red Sox and New York Yankees, both of whom have appeared beatable in recent years, are ascendant again, and there are few realistic scenarios in which the Orioles can construct a 2018 roster that closes the gap with them.

Trading Machado now could transform the Orioles’ farm system overnight, in a way that even Britton and Brach, two highly coveted relievers, could not. Even in the midst of an underachieving season, he would be in the discussion of the best players ever dealt at the deadline, given his age (25) and accomplishments. He essentially has twice the value this July as he would have next, as a contender would get his services for two stretch runs, instead of one, before he hits free agency.

Of course, Machado’s transformative powers as a trade piece assumes the Orioles’ front office nails the return, an assumption it hasn’t earned given its trade misfires in past summers and some of the additional free agent busts (Ubaldo Jimenez comes to mind) of recent winters.

Smart people in baseball have been wrong about the Orioles before, with the preseason sabermetric projections consistently underestimating their win totals. What they have done these past half-dozen years, with three playoff appearances, one division title and a trip to the AL Championship Series in 2014, should not be minimized, even if they fell short of the ultimate prize.

Some of the best teams in baseball in recent years — the 2016 Cubs, the 2017 Astros — have willingly taken steps back to make their leaps forward. But the Orioles, by trading Machado, would not necessarily set themselves on some gruesome, five-year rebuilding course, full of 100-loss seasons. If it’s done right, with the team getting back a slew of high-level, high-impact, close-to-big-league-ready players — combined with some of the core players they already have — they could be right back to contention in 2019.

The Orioles don’t need to trade Machado; as an arbitration-eligible player, his salary ($11.5 million) isn’t killing them this year, and even with a sizable raise, it won’t again next year. He would still be a relative bargain. And they certainly don’t want to trade the best player to wear an Orioles uniform in a generation or more. He is the kind of player you envision building around for a decade or two.

But when emotion and imagination are taken out of the equation, and all that’s left is the cold, hard reality of baseball economics and philosophy, the smart thing to do would be to shop Machado this month, and if the right deal presents itself — let’s define that as a deal that puts the franchise on course for an era that equals or tops the one that may be ending now — jump at it.