This winter, Robinson Cano will be the biggest, most expensive name on the free-agent market, which is just the sort of player the big-market, deep-pocketed New York Yankees have been known to land.

But will they? And more importantly, should they?

Cano, of course, actually is a Yankee. At least, technically speaking. For now.

Fresh off his 31st birthday—celebrated in style along with his rep Jay Z in Belgium—Cano remains property of the Yankees until the end of the World Series, although it’s all but a formality that he’ll hit the open market and be the most sought-after superstar of the winter.

Among the many questions the Yankees face this offseason, solving the Cano Conundrum should be priority No. 1. But there are oh-so-many layers and nuances and variables to complicate this situation.

Sure, Cano has said he “loves this team”—meaning the Yankees—according to Bryan Hoch of

And general manager Brian Cashman has made it clear that the club wants to bring Cano back:

We’d love to have Robbie back. There’s not much more for me to say about that, but our intention is to have him back if we can. He’ll receive without question, or has received, a significant offer to stay. He’ll have something legitimately to ponder.

And of course, amid what’s shaping up to be an offseason and 2014 season full of change, the Yanks could use some stability by keeping their five-time All-Star and best all-around player.

But despite all of that, the most important fact is that if Cano is going to remain in pinstripes, it needs to happen more on the Yankees’ terms than on Cano’s—especially when Cano’s apparently are $305 million over 10 years.

Recent baseball history has shown that paying a franchise player massive amounts to stick around isn’t necessarily the smartest way to spend, especially when they’re over 30, as Cano is. For every Joey Votto, there’s a Ryan Howard.

Nor is it recommended to splurge on the top free agents; just ask the Los Angeles Angels about Josh Hamilton and Albert Pujols or the Boston Red Sox about Adrian Gonzalez and Carl Crawford.

Indeed, there are several examples of big-name, big-money players who have moved on when their team wouldn’t meet their too-steep contract demands. And surprisingly—or perhaps not so surprisingly anymore—many of the teams turned out better for it, both in terms of on-field success and financial freedom.

In fact, if any team should be wary of the pitfalls of ponying up for an aging superstar, it’s the Yankees, who have done so to get or hold on to (deep breath now) Alex Rodriguez, Derek Jeter, CC Sabathia, Mark Teixeira and A.J. Burnett, among others.

Obviously, not all of those were regrettable decisions either at the time or in hindsight—the Yankees, remember, did win the 2009 World Series after spending big—but it’s also hard not to look around the league these days and see small-market clubs like the Tampa Bay Rays, Oakland Athletics and even (gasp) the Pittsburgh Pirates get it done without breaking the bank. Or even the piggybank.

The good news for the Yankees is that they already have a blueprint for handling the Cano negotiations. Back in November of 2010, Jeter’s previous contract came to an end, and after proposing an offer, Cashman more or less challenged the longtime captain and shortstop—one of the best, most revered players in the franchise’s long, storied history—to see if he could do better elsewhere.

Granted, taking that strategy to the public forum wasn’t the smartest thing for the organization to do, especially with Jeter and in media-crazed New York—it wouldn’t be recommended with Cano either—but that same take-it-or-top-it approach is the Yankees’ best play.

Put a big, fat number in front of Cano, one that fits the team’s budget and terms, and make it clear that’s where the line gets drawn.

The Yankees already made a “significant offer” to Cano several months ago—$161 over seven years, per David Waldstein of the New York Times—and maybe even more than one. But that should be thought of as the let’s-get-these-talks-started proposal more than a hard-and-fast one that’s likely to come soon enough.

The Yankees should be spending these last few days of exclusive negotiating rights with Cano to line up their best—and final—offer. And if Cano, under the advisement of Jay Z’s Roc Nation Sports says nah, then Cashman should respond by saying that the offer stands, but not for long, and if Cano can do better, well, then thanks for playing.

Because in Cano’s case, even as the top target this offseason, there won’t be that many suitors able to give him the money he wants or expects. While it might be a little premature to automatically count out any small-market team, it’s more than likely that only teams with big budgets will be in the bidding.

Obviously, the freedom to negotiate with all 30 teams on the open market gives the player a huge advantage and lots of leverage. But in Cano’s case, he he simply won’t be talking numbers—real, serious, nine-figure numbers—with more than a handful of clubs.

As Tom Verducci wrote for Sports Illustrated:

Ultimately, Cano’s value will be determined by a team other than the Yankees, be it the Dodgers, Cubs, Nationals or Rangers or a team nobody sees coming, such as the Mets or Marlins. Cano needs to engage another club in the bidding to reach the $200 million neighborhood, a space occupied previously only by Rodriguez (twice), Albert PujolsJoey Votto and Prince Fielder.

So what “team other than the Yankees” might be the one to drive up Cano’s value on the open market to the point where he might actually get a better deal than what the Yankees could offer?

Look, it’s not as easy as saying all of the above teams are over and out, not when free agency hasn’t even begun. And the “mystery team” is always in play, always lurking. But the point is, Cano isn’t going to have this wide-open market to land a contract much bigger than what the Yankees are likely to put on the table.

A team or three will be in the mix, for sure, but at the moment you have to squint to see which ones.

From the Yankees’ point of view, if they suspect Cano and Co. are bluffing, but that he really does have another team ready to hand over more, the biggest problem is that there’s not much to fall back on at the moment, either on the current roster or in the minors.

That would put a lot of pressure on Cashman to make a few savvy—but less pricey—moves in free agency to keep the Yankees in contention. But with the millions that would otherwise be going to Cano available, Cashman would have the ability to spend as he sees fit to plug multiple holes, rather than just one.

All the more reason why that take-it-or-top-it offer should be presented to Cano sooner rather than later, so the Yankees can move on and do their shopping elsewhere, if it comes to that.

Because there’s more than one way to solve a conundrum.

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