As the old saying goes: “You can’t win the World Series in April, but you sure can lose it.”

Sadly, this looks to be the case for the struggling Red Sox—possessors of one of the MLB’s highest payrolls. Their struggles are due in large part to a fragile relationship between a developmentally-minded front office and a rabid fan base desperate for big-name players and marquee deals.

When done correctly, a developmentally-oriented system can lead to great results—enter the Red Sox of 2007, whose mixture of young talent and big-name stars led to World Series glory.

Unfortunately for the Sox, World Series glory will have to wait another year.

The long term deals given to Daisuke Matsuzaka, David Ortiz, J.D. Drew, and Josh Beckett have left the BoSox with four players for whom the only thing higher than their profile is their salary. All four of these marquee athletes look like shadows of their former selves and are a burden on the balance sheet, as well as the field.

The fact is that Red Sox general manager Theo Epstein dreams of running an organization similar to the Rays or Athletics of the Moneyball Era. Epstein stresses prospect development and often shies away from large free agent signings.

On the other hand, the fan base in Boston pressures the team to sign big-name players in order to justify skyrocketing ticket prices.

Believe it or not, Red Sox fans want the organization to spend like the Yankees while maintaining an identity of development like the Rays.

A brief look at recent history lends itself to the revelations that A-Rod almost signed with Boston, that the Yankees investment in C.C. Sabathia could have been matched by the Red Sox offer to Roy Halladay if a trade had been worked out, and that the Red Sox were angered not by the size of Mark Teixeira’s contract, but by the fact that they were never given the opportunity to match it.

The Red Sox’ and Yankees’ payrolls are so similar because the organizations are similar. Boston is not the Mecca of homegrown talent, as some fans would have you believe, but is as much of a haven for overpriced free agents as New York (see: John Lackey and Victor Martinez).

The problem is that while the Yankees will shamelessly spend a quarter of a billion dollars in one offseason to provide the tangible benefit that is a World Series—the Red Sox simply will not. They will still hang on to their developmental mentality and thus avoid the big money, but sure-thing free agent opportunities.

When was the last time the Red Sox signed a “sure-thing” free agent?

For the Yankees, C.C. Sabathia, Mark Teixeira, and A-Rod immediately come to mind. The Red Sox, on the other hand, leave us pondering the day when Matsuzaka and Drew live up to the hype.

Ironically enough, Boston has made recent major acquisitions through blockbuster deadline deals (see: Bay and Martinez) which have shipped out some of Epstein’s most beloved prospects.

As past seasons have shown, this formula is no longer working. Maybe the pre-Epstein era duo of David Ortiz and Manny Ramirez made the young executive’s team overachieve its way to two World Series titles.

However, even the Josh Beckett deal—which many people credit for the 2007 World Series victory—involved losing Hanley Ramirez, one of baseball’s emerging superstars.

Again, big-name players at the price of a diminishing farm system.

Meanwhile, the real measure of success in Boston has changed from playoff appearances to World Series victories.

While the outlook may be bleak in baseball’s most top-heavy division, the Red Sox have an undeniably talented nucleus of young players.

Jon Lester, Jacoby Ellsbury, Dustin Pedroia, Kevin Youkilis, and Victor Martinez are here to stay—and with the impressive play of the Rays and Yanks, the BoSox will need all the help they can buy…or develop that is.

Read more MLB news on BleacherReport.com