When the White Sox announced their interest in pursuing superstar free agents Manny Machado and Bryce Harper at the December Winter Meetings, Major League Baseball was, well, stunned isn’t the right word. But the league was certainly surprised. A team coming off a 100-loss season, deep in the middle of a rebuild beset by injuries and setbacks, with dwindling attendance in a city dominated by the Cubs, was suddenly trying to make a splash by signing one of the two biggest free agents in recent memory.

But what if the White Sox don’t land Harper or Machado? Manager Rick Renteria, General Manager Rick Hahn, and even first baseman Jose Abreu have all remained upbeat — as they should — that the internal improvements the Sox have made across the last several years will be enough to carry the team across the finish line eventually.

The farm system is stacked, with six prospects on MLB Pipeline’s Top 100 Prospects list. This includes Michael Kopech, whose 2018 major league debut was shortened by a surprise Tommy John surgery, and Eloy Jimenez, acquired in the Jose Quintana trade with the Cubs. Jimenez is expected to join the team in early 2019 and have an immediate impact, while the other prospects remain waiting, and maturing, in the wings. The Sox should have no shortage of talent coming up in the next one or two years.

Despite one of the best farm systems in baseball, the White Sox will not and cannot have every piece they need for “sustained success” come up from the inside. At some point, outside acquisitions will have to be made to supplement the talent already in place. Signing Manny Machado is one such move, and would be an early one considering their projected competition window, but he could also be the piece that cements the rebuild as a long-term success rather than a long-term failure.

But as the winter has dragged on, and as Harper and Machado have continued to hold out, the obstacles for the White Sox to sign one of them have been thrown into stark relief. One, the White Sox have to battle the perception that owner Jerry Reinsdorf is cheap and would rather see Machado or Harper go elsewhere than open his checkbook to secure a deal. Two, the window for competition is not supposed to open until at least 2020, and so signing a superstar to a long term deal with an incomplete team might be proving to be a more difficult selling point than anticipated. Three, other teams on the tail end of their rebuilds — the Padres and Phillies — have both made serious pushes that threaten to undermine the White Sox’ recruiting efforts. And finally, market forces are shaping free agency more than players or teams anticipated.

It is this last point, especially, that seems to be the most serious obstacle to landing Machado. How is the market value of a player determined? How does the fact that both free agents are “generational talents” factor in to a team’s offer? Did the end-of-season declarations that Machado and Harper both expect long term, $300 million-plus deals affect the offers they received? Do long term deals even make sense for teams anymore? Are the players greedy for holding out, or are teams being unfair assessing their value? Has the Wall Street players-are-commodities mentality completely overrun front offices around the league? How will this offseason affect relations between the league and the player’s union? And for the White Sox specifically, will they be outbid because they misread the market and their own standing in it? None of these questions have easy answers, but they will have to come to a head at some point.

The White Sox could very well find themselves answering many of these questions the hard way if they fail to sign Machado because he was offered the kind of deal he wanted from the start. If he goes to San Diego, for example, the White Sox strategy to respond to the market instead of leading it will be completely invalidated, and the Sox will have to take a different approach to next year’s free agent class. Machado signing with the Padres, especially for 10 years and over $300 million (assuming there is no bidding war that drives up the price), will discredit the White Sox’ valuation methods as well — and will send a message not only to them, but to the league, that players may actually be worth what they are demanding.

But if Machado does come to the White Sox — if the reported offer of 8 years and $250 million turns out to be true — their assumptions about the free agent marketplace will be completely validated. The bargaining position of the players will also either be dismantled or emboldened (we won’t know until next winter), but the team will win more games and fill seats — and, perhaps, pry open their window a little earlier than expected.