Will the Yankees' experience with Alex Rodriguez (above left) affect how much they are willing to pay Robinson Cano (above right)? Associated Press

The Yankees have no doubt pored over every word of Alex Rodriguez's contract in recent days, searching for something akin to an escape hatch. And maybe, if everything breaks just right, they'll eventually find one. Hope springs eternal.

But chances are, they won't. Chances are, they will continue to curse the day that Hank Steinbrenner, in his brief reign over the Yankee empire, authorized the 10-year, $275 million deal in 2007.

Far more significant is what the Yankees decide to do with Robinson Cano, their best player, a potential Hall of Fame second baseman and a free agent next winter. Trying to keep him is a no-brainer. The question is how far they'll go to do so—and how their experience with the A-Rod contract will color their thinking, if at all.

At a time when the Yankees are seeing, more than ever, the perils of a long-term megadeal with a 30-something player, they are likely just months away from pursuing a long-term megadeal with a 30-year-old player. Cano, who is making $15 million this season, might not get 10 years or $275 million from any team. But it shouldn't shock anyone if he ends up getting an offer of $200 million or more, especially if the Los Angeles Dodgers get involved.

Two years ago, Cano ditched his former agent, Bobby Barad, and hired Scott Boras. You don't hire Boras to settle for a modest deal from your current employer. You hire Boras to give yourself the means to purchase a small country. That's what Rodriguez did, and the result was two record-breaking contracts.

What the Yankees must ask themselves is this: Is there anything to be learned from the A-Rod mess that applies to Cano? Or are the two of them so different—and the need to keep Cano so great—that the Yankees should pay whatever it takes?

The sting of the A-Rod deal is impossible to ignore. It's not only still fresh; it's getting worse by the day. But two Yankees executives played down the idea that it would affect their thinking with Cano.

"I think every individual situation will be evaluated with all the specifics to that individual," general manager Brian Cashman said. "We'll act accordingly every time a circumstance comes our way and we'll make decisions based on what we feel is the right thing to do at that moment in time."

It's hard to believe the Yankees, with all of their financial might, would allow a homegrown star to leave in his prime. If they disappoint this season, it would be even harder to imagine.

But this is no longer a team operating without financial limits. They may be self-imposed, but they exist. Owner Hal Steinbrenner is on a mission to get the payroll under $189 million by next year. And he revealed last month that it's not just a one-year target.

That still leaves plenty of money to lock up Cano, whatever the cost. It just leaves less left over, so if Cano's health or production takes a nose dive in his mid-to-late 30s, it may not be as easy for the Yankees to spend their way around it.

Cano, who turned 30 in October, has been the picture of durability so far. Since 2007, he has played an average of 160 games per regular season. Only two other players have appeared in more games over that span: Prince Fielder and Adrian Gonzalez. Both are first basemen, meaning they play a less demanding position than Cano. And neither has been as valuable as Cano, in terms of marginal wins added to their teams.

But it's easy to forget that Rodriguez was nearly as durable and far more valuable over the same span in his career. Rodriguez averaged 158 regular-season games per year during his age 24-to-29 seasons and was worth nearly twice as many marginal wins.

Cano has never made a spectacle of himself the way Rodriguez does so routinely, and that counts for something. But the day is coming when he will push the Yankees for a market-setting deal, just as Rodriguez did. And you wonder, if they're pushed to the brink of their comfort zone, how easily the Yankees can forget about the buyer's remorse they feel today.

Write to Brian Costa at brian.costa@wsj.com