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When Is Perfect Time to Trade Harper, Machado and Rest of Lauded '18 FA Class?

The countdown to 2018 began a while back. Everyone in baseball could see it coming because the names were too big to ignore, the dollars too big to even imagine.

Bryce Harper. Manny Machado. Josh Donaldson. Zach Britton. Andrew Miller. All ready to hit the free-agent market the same winter.

Clayton Kershaw. David Price. Both have opt-out clauses that could send them into that same market.

The countdown is real, both for the players about to cash in and the clubs that dream of signing them. But the countdown is just as real for the teams that could lose them and get only the value of a draft pick (reduced in the new collective bargaining agreement) in return.

Decision time is coming quickly, and the choices those clubs make over the next 19 or so months could be every bit as important as the ones players and teams make two years from now.

Can they sign their stars? Do they play it out and hope for the best? Do they try to cash in and avoid the risk?

The result could be the biggest trading market ever, leading to the biggest free-agent winter ever. But if you're a team that can't sign your star, when exactly do you try to move him?

"Good question," said a National League general manager who doesn't have any of the biggest stars. "My guess is next offseason or maybe as early as this summer."

Another NL executive predicted the Washington Nationals could trade Harper after the 2017 campaign and that the Baltimore Orioles could trade Britton. He figures the Orioles will hold on to Machado in hopes of signing him to a new contract.

But former Colorado Rockies general manager Dan O'Dowd, now an MLB Network analyst, expressed doubt any of the biggest stars will be dealt. Their teams are trying to win now, he reasoned, and the return wouldn't be big enough to justify a move.

"When your club has a chance to win, it's very problematic," O'Dowd said. "No matter how good the prospects are, they're still just prospects. The new CBA makes it tougher too, because it's harder to trade the impactful young players you'll need to balance out your big contracts."

O'Dowd and others believe teams will want to avoid the harshest luxury-tax penalties, which can rise to as high as 92 percent at the highest levels. The easiest way to do that is to have talented young (and thus cheaper) players to mix into your roster.

Top prospects will still get traded, as shown by the return the Chicago White Sox got this winter for both pitcher Chris Sale (from the Boston Red Sox) and outfielder Adam Eaton (from the Nationals). But the Red Sox got three years of control with Sale, who has a reasonable contract, and the Nationals got a potential five years of control with Eaton.

A team trading for a 2018 free agent now would have two years of control. But the only prominent class members who have come up in serious trade rumors this winter are Pittsburgh Pirates center fielder Andrew McCutchen and Minnesota Twins second baseman Brian Dozier.

Neither has been dealt.

It makes sense for their teams to keep trying, especially the Twins, who have little chance of winning in 2017. The Pirates might do better waiting to see whether they can stay in the NL Central race and/or whether McCutchen can rebuild his value by bouncing back from a subpar 2016.

What about the others?

Some aren't realistic trade candidates. Price and Kershaw pitch for teams aiming for a championship. Mark Melancon has a 2018 opt-out, but it's in a contract he signed with the San Francisco Giants in December. They're not trading him now and almost certainly wouldn't move him next winter, either.

The harder ones to predict are the other 2018 free agents playing for going-for-it teams.

If the Orioles fall out of the race early, would they consider dealing Britton and/or center fielder Adam Jones, helping free up money to try to sign Machado? If the Toronto Blue Jays fall out of it, could they market Donaldson to a team needing a second-half boost? Could the New York Mets offer pitcher Matt Harvey to help fill other needs?

It's hard to see the Cleveland Indians dropping too far behind in the American League Central, but what if they did? Could Miller be a midseason trade candidate for a second straight July? They might get even more than the high prospect price they gave up to the New York Yankees to get him.

Then there's Harper, who will have just turned 26 when he hits the free-agent market. He's a big part of the Nationals' plan to win in 2017, but would they move him if they don't?

Several executives said midseason 2017 trades could be the most realistic option for big-ticket free-agents-to-be.

"Teams can be desperate, and there aren't free-agent options available in July," one AL executive said. "And a team can trade for a guy knowing they can have him for two pennant races."

With so many top players a year and a half away from free agency, the buy-sell decisions could be tougher and more significant than ever this July. Keeping a player until next winter could severely limit the potential return and thus make it less likely the player gets moved at all.

No matter what, July figures to be fascinating. Next winter could be interesting, as those same teams try to judge their chances of winning in 2018 against the risk of getting only draft picks back for departed stars.

It all leads up to November 2018, and the start of a baseball winter like none we've ever seen.

                   

Danny Knobler covers Major League Baseball as a national columnist for Bleacher Report.

Follow Danny on Twitter and talk baseball.

Read more MLB news on BleacherReport.com

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