There's a reason the phrase "prospects will break your heart" exists.

Here's a #HotTake: the Yankees have struggled to produce major league caliber players from their farm system for quite some time now. Yes, this is a stunning development. All the luck the Yankees seemed to have in the early '90s when they conjured up three very long careers out of mostly unheralded prospects Andy Pettitte, Jorge Posada, and Mariano Rivera has not followed them into the new millennium. The last productive position player prospect they churned out was Brett Gardner. While since the mid-'90s they've been typically able to supplement this core with a couple universally well-regarded prospects who worked out in Derek Jeter and Bernie Williams and a plethora of free agent signings and trade acquisitions, that well is about to run dry with the retirement of Jeter, the last active player from that youth movement.

The easy excuse would be to blame management for not doing a better job at producing prospects, but the fact of the matter is that it is incredibly difficult to do so and almost unprecedented to have so many prospects work out at once the way Rivera and company did. That being said, one would expect the system to have produced homegrown products at least a little better over the past 15 years or so around the majors than Gardner, Phil Hughes, Austin Jackson, and company. Of course, it's not a problem unique to the Yankees--producing "the next Core Four" is simply expecting far too much. It's a challenge to produce homegrown players. Look at the Oakland Athletics, who have had the best run differential in baseball this year. They have precisely two homegrown players on their roster: closer Sean Doolittle and starter Sonny Gray.

I don't think I'm wrong in saying that the general feeling around Pinstripe Alley is that we enjoy prospects. I know I do. It's exciting to look toward the future and hope for the best. The harsh truth of baseball though is that the cliche is true: prospects will break your hearts. One way to bring prospect expectations back to earth is to look at old top prospects list. Baseball America has all of its Top 100s available to the public dating back to 1990. While some of those players went on to great careers, most were just mediocre or never made it at all. The same can be said of the Yankees' own top ten prospect lists from years past. While the Yankees have admittedly not had as great a system as those in other franchises, the difficulty in succeeding in the majors is still apparent.

Take a look back at Baseball Prospectus's top ten Yankees prospects as of the end of the 2009 minor league season, roughly five years ago today. These players have now had five professional seasons to define their careers. So where are they now?

1) Jesus Montero - C

The cream of the crop and so far, one of the biggest prospect busts of all time. He wasn't just the top Yankees prospect--from 2010 through 2012, both Baseball America and Baseball Prospectus ranked him among their top seven prospects in all of baseball for three years in a row, reaching as high as number three overall on both lists in 2011. After the '09 season, BP's Kevin Goldstein (who now works for the Astros) wrote:

Simply put, Montero is one of the best offensive prospects in the game, and possibly the best. He's a massive slugger with the contact skills of a batting champion, with one scout classifying his ability to put the middle of the barrel on the ball "almost supernatural." His raw power is at or near the top of the charts-and he's just starting to tap into it. He has the potential for 30-40 home runs annually. He's a hard worker who puts as much work into his defense as his hitting, and he's made great strides behind the plate... though he remains a well below-average catcher.

Goldstein said that Montero was possibly the best offensive prospect in a class that included Giancarlo Stanton and Buster Posey, just to name a couple players. That is heavy praise.

Of course, Montero never made it as a catcher. He was so dreadful behind the plate that after trading for him in 2012, he only caught 85 major league games for them before the Mariners ended the experiment. Even more damning is that his bat has not translated to the majors at all. Despite promising numbers in a 2011 September call-up with the Yankees, he has hit only .251/.291/.378 in Seattle with an 89 OPS+ in 170 games. He was suspended 50 games for his involvement in the Biogenesis PED scandal, and he showed up to spring training 40 pounds overweight this year and told reporters that he basically did nothing all off-season. He thus spent all but six games this year in Triple-A, and he was not called up in September, partially I'm sure as a result of the now-infamous ice cream sandwich incident.