Are the Yankees finally learning their lesson?

If I could sum up the Yankees front office over the last few years in one word, terms like "thickheaded" or "stubborn" would arise more often than any of us should feel comfortable with. It’s certainly the case that Brian Cashman has been no slouch as a General Manager, making a number of legitimately good moves recently, but for most of the time he has had to heel to the whims of Hal Steinbrenner and Randy Levine. Thankfully—mercifully—it seems in 2014 the Yankees have learned their lesson.

It started last season when, in an effort to supermount the $189 million tax bracket, Steinbrenner and company assembled the 2013 squad—a flimsy roster stocked with part-timers and has-beens. The disaster was accentuated after injuries crippled the team. By the end of the season, the Yankees had missed the playoffs for just the second time in nearly twenty years. They supposedly entered this offseason with Plan $189 still intact, but as we’ve seen, they’ve since shed the shackles of their ‘fiscal responsibilities.’ It’s apparent that the team values winning over saving a few million dollars—just as it should be. Of course, we might never know the real reason—it might be to save face, garner better attendance, or simply, as aforementioned, to create a winning team. But as crazy as it may sound to some, spending nearly $500 million on the team was the right decision to make.

Plan $189’s biggest flaw was that it was reactionary. The new rule change swept in threatening to punish the team for its free-spending ways, and the Yankees did not have the infrastructure in place to replace high-dollar free agents with less expensive internal alternatives. The decision to not spend this time last year left the Yankees with sub-par replacements and scrapheap pickups. Now, the Yankees are a much better team with Jacoby Ellsbury, Brian McCann, Masahiro Tanaka, and Carlos Beltran. It has certainly loaded their wagon with more long-term contracts, but such is the free agent game. The Steinbrenners may very well want to slice the payroll, but it cannot happen in one fell swoop. A structure must first be in place before changes are made.

That's where the farm system comes in. The Yankees succeeded in the 2013 draft and now they are looking to make a splash in the international amateur market. These players won’t help the team right this moment, but this new direction will certainly help them in the future. This is the new infrastructure the Yankees need to continue to bolster if they ultimately want a smaller payroll. Smart baseball decisions will get them there.

A few months ago the Yankees were faced with an unenviable decision: to either sign one of their star players (and "potential face of the franchise" following Derek Jeter’s departure) Robinson Cano to an expensive and long contract, or to let him move on to another team willing to dish out the cash required. The Yankees couldn't take the chance of signing another player over the age of 30 to a ten-year deal. The last thing this team needs is another Alex Rodriguez. While I wish they had kept Cano, I can't say that a ten-year, $240 million contract would have impressed me. The Yankees' long policy of not offering extensions to players has cost them the likes of Nick Swisher and Curtis Granderson. Now it cost them Cano. They seem doomed to repeat the same mistake over and over. As more and more teams have dished out the money to lock up their young players, the Yankees' constant flow of free agent talent will certainly dry up.

Looking ahead to the 2015 free agent market, Brett Gardner might have been the best outfielder available. Not anymore—as impossible as it might sound, the Yankees just signed Gardner to an extension. Have they learned their lesson from losing Cano? There are other players that deserve extensions too—David Robertson, for instance—so we’ll have to wait and see if this is a behaivor they repeat again. It was certainly a smart move to lock up Gardner. Cashman has long liked Gardner's defense and speed and so he offered a friendly deal—perhaps better than he would have gotten on the open market (potentially $15 MM AAV and up to six years). Now the team has their starting outfield taken care of for the next few years and they'll be able to focus their efforts elsewhere. This extension was a smart baseball decision.

If the 2013 season was an example of an organization not learning from their mistakes, 2014 would appear to be the opposite. There have been lessons learned in three ways: not handing out a monster contract to Cano (learned from the Rodriguez experience), handing out an extension to Gardner (learned from the Cano experience), and focusing more on the farm. So it is possible that the days of the team's no extensions policy are behind them, and that they are refocusing their efforts on the farm system, and are taking chances and trying new ways to find value. Sometimes they will fail, other times they will succeed, but if they continue their efforts, they'll get everything they want and more. They seem more than capable of finding the next Cano, and this time, hopefully, they'll do it right and never let him slip through their fingers.