ST PETERSBURG, FL - MAY 27: Manny Machado #13 of the Baltimore Orioles exits the field after scoring in the first inning against the Baltimore Orioles on May 27, 2018 at Tropicana Field in St Petersburg, Florida. (Photo by Julio Aguilar/Getty Images)

It’s all but a foregone conclusion that the Baltimore Orioles will be trading Manny Machado this year, but there’s a good chance they’ll screw it up.

It’s all but a foregone conclusion that the Baltimore Orioles will be trading Manny Machado before the non-waiver trade deadline this year. As of now, the team is one of the worst (if not the worst) teams in the majors—the only team to have not won 20 games yet.

As it stands, the Baltimore Orioles need to enter rebuilding mode, and the first step towards that will be trading Manny Machado to a contending team who will, in turn, send them a haul of quality prospects.

But they’ll find a way to screw it up. Call me cynical—I think it’s hard to find a non-cynical Orioles fan at this point—but given the Orioles’ history of blockbuster deals and the power dynamics going on in the front office right now, I’m not optimistic.

Machado is a rental, that much is abundantly clear. He’s not going to give any team he’s traded to an advantage towards signing him—he’s going to be a free agent, and that could be a tough sell for a team to send big-time prospects in exchange for him, especially considering how poor the market was for rentals last year.

Other MLB executives have expressed as much to The Athletic‘s Ken Rosenthal (subscription required). Rosenthal writes that he had a text conversation with an MLB executive who will likely not be involved in trading for Machado, and he said that “rentals faced a brutal market last summer,” and that he’ll be “eager to see if that continues or if teams will be willing to pay more to acquire players for a few months of contributions.”

He added that he wouldn’t be shocked “if [the Orioles] hold [Machado] because the returns will be underwhelming compared to the [Aroldis] Chapman type of return.” Chapman was traded from the New York Yankees to the Chicago Cubs in exchange for infielder Gleyber Torres, outfielders Billy McKinney and Rashad Crawford, and pitcher Adam Warren.

The Baltimore Orioles are in the throes of one of their worst seasons on record, looking to ultimately trade perhaps the best talent their system has developed in the past decade in a market that’s suggesting a superstar rental might not provide the returns the player deserves, with a fractured management team who no longer trusts the only member of that management team…with considerable experience actually negotiating trades.

That haul that the Yankees got for Chapman, that’s what the Orioles should get considering the type of player Machado is. But when you look at trades like the one that sent J.D. Martinez to the Arizona Diamondbacks in which the Tigers got Dawel Lugo, Sergio Alcantara, and Jose King, it’s not particularly encouraging (for reference, Lugo is the best prospect of that deal, and he’s the 12th-best prospect in the Tigers’ system).

So for basically any team, not just the Baltimore Orioles, trading Machado as a pure rental and getting high-level prospects in return would be difficult. But when you add in the power struggles (subscription required) going on within the Orioles’ organization, things get even dicier.

Rosenthal also reports (unsurprisingly) that the power dynamics within the Orioles’ organization are—to put it lightly—a bit strained.

Obviously, you’ve got Dan Duquette in the final year of his contract, and according to Rosenthal, that’s led to Duquette losing a fair bit of influence. The writing is pretty much on the wall, this is Duquette’s final year with the Baltimore Orioles, he’s not coming back next year. So why would he have that much influence on the team?

Meanwhile, Peter Angelos is hardly involved with the team at all, and instead, his sons John and Lou are more actively involved. Close to them is VP of baseball operations Brady Anderson—the man who was the driving force behind the signings of Alex Cobb, Andrew Cashner, and Chris Tillman. But Anderson isn’t interested in assuming Duquette’s role, he likes moving around behind the scenes.

So we’ve got the Angelos brothers, Anderson, Duquette, and of course, Buck Showalter all vying for a place in the decision-making process, all with different ideas of how this team should be run. So who’s in control right now? I haven’t the faintest idea, and neither does anyone else.

So let’s review—the Baltimore Orioles are in the throes of one of their worst seasons on record, looking to ultimately trade perhaps the best talent their system has developed in the past decade in a market that’s suggesting a superstar rental might not provide the returns the player deserves, with a fractured management team who no longer trusts the only member of that management team (Duquette) with considerable experience actually negotiating trades.

Let’s not forget that while the Orioles are exploring the Manny Machado trade market, they also have Adam Jones, Zach Britton, and Brad Brach all on the final years of their contracts, all potentially tradeable.

Forgive me if I seem overly-cynical, but I don’t exactly have a ton of confidence in the Baltimore Orioles’ management team in the state that it’s currently in juggling all of the different moving parts as we approach the trade deadline and ultimately coming away in a better position to develop a winning team than they were in before. Remember, this horrible season was not part of a rebuilding year, this was the Orioles’ front office’s attempt at building a playoff contender.

I might be wrong. I hope I’m wrong. I hope the Orioles trade Machado and Jones and Britton and Brach and basically anyone not named Jonathan Schoop, Trey Mancini, Dylan Bundy, and Kevin Gausman (and I could even be persuaded into trading those last two), and I hope they come away with prospects that can make Orioles fans excited about the future for the first time in a long time.

But this is the Orioles we’re talking about. They’ve let me down before, and I’m hard-pressed to be particularly optimistic that they won’t let me down again.