It was inevitable. With everyone waiting on Bryce Harper and Manny Machado to sign -- not to mention the roster machinations teams are doing in preparation of next offseason's hot stove (namely free-agent-to-be Paul Goldschmidt being traded) -- we were invariably going to end up discussing what might be baseball's biggest story over the next 20 months: The looming free agency of Michael Trout, which is set to happen after the 2020 season.
Trout's name was floated Tuesday when MLB Network insider Jon Heyman, while discussing the Phillies' ongoing pursuit of Harper or Machado, noted that the Phillies are already looking two years down the road to make a play for Trout when he hits the market:

It is a surprise only that it took this long for Trout to get dragged into this. In case you've forgotten, Trout -- baseball's greatest player, and somehow still only 27 years old -- has only two years left on the six-year, $144.5 million extension he signed in March 2014. Suffice it to say, the Angels have gotten their money's worth on that contract: Trout has produced 44.4 WAR in the five seasons since he signed the deal, which is more than a number of Hall of Famers produced in their entire careers. But not a single one of those seasons has ended with a postseason victory. That Trout still hasn't won a postseason game (the Angels were swept in the '14 American League Division Series by the Royals, his only playoff appearance) is a little bit sad for all of us.
And, well, the Angels don't look any closer to a playoff spot than they have been the past few seasons. They were below .500 in 2018, 17 games behind the A's for the second AL Wild Card slot, and when you consider that Shohei Ohtani won't pitch in 2019 as he recovers from Tommy John surgery -- and could be limited as a hitter -- you have to squint to see them having a path to make it in '19. The Angels have a chance to reach the postseason by virtue of being a team that's actually going to floor it, but there are holes in that roster, as '18 proved. Even with the head start having Trout gives them, making the playoffs this season is an uphill climb.
So, then: What happens if the Angels are nine games or so out of a playoff spot at the Trade Deadline, like they were in 2018? If they're as far away from an extension as they seem to be, don't they have to explore trading Trout? After all, we've seen how even some of baseball's biggest stars fail to bring back much in trade when they only have one year left on their deal, like Trout would if the Angels waited until after the Deadline to deal him. The Cardinals got Goldschmidt, one of the best hitters in the game, for right-hander Luke Weaver and catcher Carson Kelly, two promising young players but not clear difference-makers.
Trout would bring back more than that, but not dramatically so, and certainly not enough to serve as a foundation for a rebuild, the way the White Sox did with their trades of Chris Sale and Jose Quintana, each of whom had multiple years left on their deals.
The Angels don't appear to be making headway on an extension. The Halos aren't a top-tier contender. And Trout's value on the market essentially falls off a cliff after the 2019 Trade Deadline, because at that point you are only getting him for one potential postseason push as opposed to two. These three factors could combine to make it downright irresponsible for the Angels not to consider a Trout trade.

And, uh, I suspect there would be some interest.
As Heyman notes, the fact that the best player in baseball could quite possibly be on the market in the next six months -- and will definitely be on the market in the next 20 -- is surely something teams are keeping in mind when they make plans for 2019 and beyond. So what happens if Trout hits the trade market in July?
The usual suspects would be involved, you'd think: The Yankees, Red Sox, Dodgers, Cubs ... the big boys. But the fun of having Trout on the trade market is that as long as you can take on Trout's short-term salary -- he'll make $66.5 million combined in 2019 and '20, an absolute steal -- you can have Mike Trout (Mike Trout!) on your team without having to give him the biggest contract in the history of the sport. (Remember, Trout will be only 29 when he hits the market. Yikes.) So if you have a deep, talent-rich farm system and you're in contention next July, you get to play. That opens up the bidding outside the biggest spenders.
Imagine if, say, the White Sox are still hanging around the Indians in July. We know they have the prospects, because it wasn't long ago they traded for them. What if the Padres, with their trove of prospects, decide it's time to make the big move A.J. Preller is clearly itching to be a part of? The Cardinals have a gaggle of disposable young pitchers that the Angels could build around for the next half-decade; if they don't get right field resolved by July, would they jump in? Houston? Philadelphia? Maybe even Tampa Bay decides they can pay for Trout as long as it's only a year and a half. Sky's the limit!

The most intriguing candidate, though, would probably be Atlanta, a team with top-shelf starting-pitching depth and one that will likely find itself in a dogfight in its division this year. That franchise might be hesitant to spend on a long-term Trout but would surely leap at a pennant-chase Trout. And the Braves have the obvious outfield need. He'd look sharp in a Braves uniform, one thinks. And can you imagine Trout and Ronald Acuna Jr. in the same outfield? Is that even legal?
One wrinkle, of course, is that Trout has full no-trade protection, so it's possible he could block a deal. But it's hard to see a scenario in which Trout doesn't want to go play for a contender, at least for a year and a half.
And then, of course, the intrigue after a theoretical trade -- when he does become a free agent -- will match and even likely surpass the current Machado-Harper sweepstakes. This is, after all, the best player in the sport, and one of the best in baseball history, available in his prime. The Phillies are now reportedly eying Trout's potential availability. They're surely not the first, and they're definitely not the last. Trout's pending free agency is going to dominate every baseball conversation over the next 20 months. Might as well start it now. Strap in.