Oct 1, 2016; Bronx, NY, USA; Baltimore Orioles third baseman Manny Machado (13) hits a solo home run to right during the third inning against the New York Yankees at Yankee Stadium. Mandatory Credit: Anthony Gruppuso-USA TODAY Sports

Manny Machado is going to command a likely record-breaking contract when he’s done in Baltimore after the 2018 season. Should the Baltimore Orioles cash in their chips?

Let’s all sit down and be honest with each other. Manny Machado is more than likely not going to sign an extension with the Baltimore Orioles this season. Most likely, he’s going to test the open market after the 2018 season and I don’t blame him, because he’s going to make boatload of money.

Between him and Bryce Harper, there’s going to be a lot of money spent next offseason, and it’s money that I don’t think the Baltimore Orioles are going to have (or be willing to spend).

It’s been reported by Ken Rosenthal that Machado’s next contract could get into the $400M range, which, while insanely high, sounds relatively reasonable when compared to Giancarlo Stanton’s $325M deal. That’s money I don’t see the Orioles shelling out, especially considering their team record is Chris Davis’ $161M deal.

Plus, will they even have that money? I mean, this offseason there’s talk of the team re-signing Mark Trumbo or going after some other outfielder (such as Ian Desmond), and any of those guys will likely command a decent-sized contract, something probably in the $15M per year range.

If the Orioles do sign someone this offseason for a contract like that, the purse strings will be even tighter, especially after the team blew $161 million on Chris Davis. Peter Angelos hasn’t been known to be the most extravagant spender in the league, and I think Machado is going to command too high a price.

So then what do the Orioles do? Enjoy two more seasons, hope he’ll take some lesser offer from the team in the offseason, and then watch the Yankees sign him for seven years, $400M? They could do that. And who knows? Maybe Machado would show some Baltimore loyalty and take a lesser offer to stay with the team, but I doubt that, and I especially doubt it if Harper signs a mega-deal that sets a precedent for what Machado should be worth.

What about trading Machado? It would seem that trading him would net the Orioles the most in return, if they assume they won’t be able to re-sign him. He’s one of the ten best players in all of baseball, so the Orioles could easily get a handful of top prospects in return (and/or maybe some good quality MLB players) for a team to get a rental of Machado.

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The question then is, when do you trade him? Now in the offseason while he’s healthy? Or do you wait until the trade deadline and trade him to a contender? Though you risk him getting injured in the latter scenario, you might be able to get a bigger return.

Honestly, I’m operating under the assumption that the Orioles won’t be able to re-sign Machado, I just don’t see it happening, so to me, it makes the most sense for them to cash in their chips and improve their team rather than just wait one more year and end up with nothing.

What makes this even sadder is that, according to Jon Heyman, an extension was all but done early on in Machado’s career, but it fell through for some reason. I should say though, that all of this assumes the Orioles are out of contention by the trade deadline. If they’ve got a realistic shot at a World Series, you keep Machado and you run with it.