If you think the winter of Manny Machado and Bryce Harper has been a crazy one, just wait a couple years for the complete madness of the winter of Mike Trout.
Yes, the game's best player is slated to hit the free-agent market after the 2020 season, and that will set off even more insanity than we're stuck in the middle of this offseason with Machado and Harper — who still haven't made their decisions, by the way.
Well, most likely because they're sick of waiting on Machado and Harper, some folks over at Bleacher Report have put together a list of their eight favorites to land Trout, and yes, the White Sox are on that list, seventh out of the top eight teams, which is one spot ahead of the Crosstown rival Cubs and behind the Los Angeles Dodgers, Washington Nationals, New York Yankees, Boston Red Sox, Los Angeles Angels and the favorite Philadelphia Phillies, Trout's hometown team.
The idea of Trout on the South Side might seem kind of pie in the sky, but so, too, were the ideas of Machado or Harper coming to the White Sox before this offseason started. And they remain in the mix for both of those guys.
Trout will likely command even bigger deals than those two end up with, and the same level of long-term financial flexibility that has the White Sox in those current derbies is the logic behind their inclusion on this list of possible Trout suitors. There are almost no long-term financial commitments to speak of as the roster currently stands, with Tim Anderson's contract being the only one that falls into that category. And so, yeah, if the books remain light, why wouldn't the White Sox show the same aggressiveness they've shown this offseason when it comes to Trout a couple years down the road?
There's nothing wrong with that thinking, but there are a few things that could drastically impact their place on that list between now and when Trout finally does hit the free-agent market.
First on the minds of fans, of course, is what happens with Machado. More broadly, it's what happens with free-agent pursuits over the next two offseasons. Should Machado pick the White Sox, the long-term financial situation becomes drastically different. While it would hardly keep the White Sox from making other additions to a roster they expect to start competing for championships at some point in the next few seasons, it could keep them from signing another mega free agent to a contract worth multiple hundreds of millions of dollars. And even if they miss out on Machado and Harper this winter, there's a loaded free-agent class next winter that's sure to draw their attention, as well, and it might be easier to convince one of those guys — Nolan Arenado, Gerrit Cole, Xander Bogaerts, Anthony Rendon, J.D. Martinez, Paul Goldschmidt, Justin Verlander, Madison Bumgarner and Marcell Ozuna could all be available — to sign up with the White Sox another season closer to contention. Any of those guys get a giant contract to come to the South Side, and that could make a Trout pursuit far less realistic.
Second, what will the White Sox outfield look like following the 2020 season? One area where the organization has a ton of prospect depth is the outfield, and Eloy Jimenez, Luis Robert and Micker Adolfo could all have made their way to the big leagues by the time the 2020 season concludes. And that's without mentioning the likes of Luis Basabe, Blake Rutherford and Luis Gonzalez. Now, while no one will argue that any current prospect in baseball would rival Trout in terms of production or value both at the plate and in the field, the White Sox might not need to add an outfielder to that group. That could mean avoiding the $400 million or $500 million expenditure that would be Trout and using some of that money to address greater needs elsewhere. While Trout might go down as the greatest baseball player ever, it's very possible the White Sox just won't be in the market for an outfielder when he becomes a free agent.
Bottom line: A lot can change and a lot probably will change. If the White Sox are in an identical position two offseasons from now to the one that they're currently in, that would be very surprising. Of course, whether things go exactly according to plan or things don't work out, nothing would preclude the White Sox or any team from trying to add the best player in the game.
White Sox fans might be so sick of what's going on on the Machado and Harper fronts that they might be terrified of an even higher-profile free-agent saga, but one thing would be certain: Those fans would love to see Trout raking for the White Sox rather than against him. While almost all of Trout's numbers are great, they have been very great on the South Side. He owns a career .373/.470/.687 slash line at Guaranteed Rate Field with eight homers and 20 RBIs in 22 games there. That includes the ridiculous three-game stretch he had back in September, when he went 8-for-11 with two homers, five RBIs, a couple of walks and a hit by pitch.
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