Fancred and MLB Insider Jon Heyman wrote a lengthy report on the status of the free-agent market this winter and chilled Cubs’ hopes of landing one of the two biggest free agents this winter. Heyman figures that the White Sox have a better shot at grabbing Manny Machado or Bryce Harper than the Cubs do with 15-1 odds (he gave the Cubs 20-1).

Neither odds are good for either Chicago ballclub, and Heyman wrote a dense report on how the Yankees and Phillies will lead the pack of bidders for Machado and Harper. Both Philly and New York have serious, even “stupid” money to spend and the impetus to consummate a deal. The Yankees have a spot for Machado at shortstop after Didi Gregorious went down with a UCL injury, and the Phillies have cause and means to snag both without batting an eye. And if the Phillies’ deal with the Mariners to swap Carlos Santanna for Jean Segura goes through, they will have cut $21 million from their already minuscule payroll. So, yeah, the Phillies are poised to spend stupid money.

But back to the White Sox and Cubs. Heyman presented an interesting argument on how attractive the White Sox could be to one or both of Machado and Harper.

The White Sox understand that the timing isn’t perfect for a run at a free agent in that their rebuild is still at least a year away from approaching fruition, which means that a great free agent will have to understand he’s in for at least one year of avoiding looking at the standings. That may not be such a big deal when we are talking about a contract of at least 10 years, which these are expected to be.

Wouldn’t it be nice for a free agent to ease into the competitive window with a team? How many times have free agents signed megadeals and suffered immediate, harsh criticism after stumbling out of the blocks?  The Sox can offer this to both players (add Patrick Corbin to this statement if Rick Hahn wants to get a little reckless) allowing them a measure of comfort on a long-term deal with the understanding that serious contention is at least one season away.

They are definitely considering it, and one rival suggested that the White Sox are hoping to make “a big splash.” Machado looks like the more likely splash beneficiary, as they have tried for him before. There is a likely need for a third baseman, though it’s fair to say the outfield is a work in progress, too. They have superb outfield prospects in Luis Robert, Eloy Jimenez and Blake Rutherford but only Jimenez is expected to be ready sometime this season (meaning sometime early in his case).

I’ve said this from the beginning: Machado makes more sense for the White Sox. The infield seems to be in flux considering the setbacks to prospect Jake Burger and Nick Madrigal‘s young career. Madrigal may reach the bigs quickly, but a 2019-debut is a stretch. If Madrigal follows through on his promise Yoan Moncada may need to move to the hot corner. And there’s always the question of Tim Anderson and whether he can stick at shortstop.

Signing Machado simplifies the equation by anchoring the infield at shortstop. Moncada would likely move to third and Tim Anderson could flip to second base. And if Madrigal pans out than Anderson moves to the outfield adding even more depth to a young corps. Signing Harper instead of Machado is still a boost to the lineup but doesn’t close any holes in the roster. In fact, adding Harper forces a position switch to either Eloy Jimenez or Harper, a move that seems to create more liabilities.

But let’s face it, all of these decisions flow through the man up top: Jerry Reinsdorf.

Owner Jerry Reinsdorf has pulled some surprises over the years (i.e Albert Belle) but one thing he hasn’t done much is work with Boras (Carlos Rodon, a much smaller deal, is one notable exception.)

My gut tells me Reinsdorf is willing to at least make competitive offers for Machado and Harper. Despite our feelings about his historically penurious ways, he has pulled the trigger on big deals in the past. However, will it be enough to yank either player from the Yankees or Phillies? Given the declarations out of Philly, I’m not confident. And the evil empire in New York always forces the bidding higher, even when they say they’re not in on players.

Heyman, according to several executives in and around the free-agent bidding, expects the sweepstakes for Machado and Harper to extend into January and February. The days of setting the market’s top when elite free agents signed first are gone. Mid-level free-agents will sign before Machado and Harper while other teams test the trade market for bargains before pushing their chips in on the top two guys.

And for all you Cubs fans, here’s what Heyman had to say:

They don’t seem to be in a big spending mood. They began the winter by delaying the decision to pick up Cole Hamels’$20-million option to make sure they cleared some payroll space first (they did so by dealing Drew Smyly). They also have a history of straining to stay under the luxury tax threshold. There is that narrative about how Harper’s best friend is Kris Bryant, a boyhood buddy from Las Vegas, but that hasn’t been heard a lot lately. They also have an issue with longtime shortstop Addison Russell, but he has plainly stated he intends to become a better person, and the Cubs may be ready to forgive and move on. (though in any case, he is no Machado.)