There is an art to the contract demand, floated out every November by the representatives of free agents across the league. Beginning a negotiation with the number you think you deserve guarantees you will be lowballed. Center the negotiation around a larger number and perhaps you come out ahead even after the haggling. 

Even so, the four players tagged with qualifying offers this offseason who remain free agents as February begins must be sweating. Former Royals starter Ervin Santana was looking for nine figures, as Fox Sports's Ken Rosenthal reported in November he was "seeking more than $100 million on a five-year deal." Rosenthal also reported in early January that fellow starter Ubaldo Jimenez's agent was telling clubs he "still expects to sign a multi-year deal at $14 million-plus annually."

The same goes for the hitters remaining. In November CBS Sports's Jon Heyman reported outfielder Nelson Cruz "is said to seek about $75 million over four years." Kendrys Morales hasn't floated any official demands -- Scott Boras prefers for his clients to keep tight-lipped -- but his market looks so bleak one general manager told Peter Gammons he "just cannot see Kendrys Morales signing until after the draft." Never a good sign.

It only gets worse with the turning of the calendar to February, typically a dead zone when it comes to big contracts. To be sure, most of the big moves tend to happen in November and December, around the Winter Meetings as front offices are at their busiest. But there has never been a $100 million deal signed in February, whereas four players (Carlos Beltran in 2005 with the Mets, Mark Teixeira in 2009 with the Yankees, Matt Holliday in 2010 with the Cardinals and Prince Fielder in 2012 with the Tigers, a $200 million pact) have signed nine-figure deals in January. Bad news for Santana.

Bad news for Cruz too -- there has never been a $75 million contract signed in Feburary or later either, with the closest being J.D. Drew's five-year, $70 million pact with the Red Sox in 2007. Only four players total have signed deals worth at least $10 million per year over three years in February -- Drew, Oliver Perez in 2009 (three years, $36 million) and another pair of qualifying offer players last winter, Michael Bourn and Kyle Lohse. 

Those latter two are probably the most illustrative cases for the four remaining free agents. CSN Philadelphia reported Bourn was searching for a $100 million contract as the 2012 season wound to an end (the CSN story is gone, but it was aggregated by NBC Sports). Although that scenario always looked outlandish, B.J. Upton signed a five-year, $75 million contract with the Braves early in the subsequent offseason and the two were considered comparable players at the time, with Upton offering a little more pop and Bourn offering more game speed and defensive chops in center field. However, nobody was willing to sacrifice the draft pick to sign Bourn until Cleveland, who had already spent their second-round pick on Nick Swisher, made the easy decision to sacrifice a competitive balance pick to add him on a four-year, $48 million contract.

Lohse, like Morales this year, was the least sought after free agent in the qualifying offer miasma. Lohse didn't sign until well into spring training, and the wait had some wondering if he wouldn't sign until after the MLB draft, at which point draft pick compensation would no longer be attached. It seemed more likely the longer Lohse waited to sign, but he had been too good over the prior two seasons (399 innings, 3.11 ERA, 121 ERA+) for teams not to jump in as rotation holes became evident in spring training. The Brewers finally signed him to a three-year, $33 million contract March 25th, four days after his agent, Scott Boras, shot down the idea of waiting until after the draft.

As a Boras client, Lohse and his camp never floated an embarrassingly high number early in the offseason. But industry predictions had Lohse earning as much as $64 million over four years, with few projecting lower than $45 million over three years.

Looking at both the Lohse and Bourn contracts, the disappointment level for both players was roughly half what either they demanded or the market projected. Now, both players had their risks -- Lohse had a 5.54 ERA in 209 innings in 2009-2010 and turned 34 in 2013; Bourn has never touched double-digits in home runs and has just one season with an above-average OPS. But these weaknesses were well known before the qualifying offers were handed out, and it seems more that the qualifying offers allowed teams to magnify these weaknesses where didn't with comparable players like Upton and Edwin Jackson (who signed a four-year, $52 million deal in the same market as Lohse).

It seems clear that both sides are still acquainting themselves to the risks of the qualifying offer. Players are reluctant to accept the deals for natural reasons -- they are generally all on the wrong side of 30 and want to get the most guaranteed money they can while on the free agent market -- but could likely make more money by accepting the offer and waiting out the season. Teams are reluctant to offer the deals for similarly natural reasons -- an unexpected $14.1 million commitment can tank an offseason plan -- but might not be submitting the qualifying offer often enough if players are going to keep rejecting them, and the compensation picks earned if players sign before the draft are quite valuable.

For now, though, it appears Morales, Cruz, Santana and Jimenez will be the victims of this feeling out period. It's hard to feel sorry for men still primed to make tens of millions over the next few years. Instead, just consider this another example of how things outside of the player's control can affect their contract negotiations. Timing is everything, and for these four, it couldn't have been much worse.