The problems within the organization start with the ownership, and primary responsibility must be assigned to managing partner John W. Henry.
Call it what you want: Arrogance. Greed. Hubris. Whatever term you use for it, Red Sox Nation (and the rest of the world) are finally starting to realize ownership has lost its way. The Boston Red Sox have, in essence, become the New York Yankees of the late 1980s and early 1990s.
Successful investment manager John Henry was involved in the ownership of several franchises at a variety of levels across professional sports (minor league baseball, the NBA and MLB). Henry and his group purchased the club in 2002, the hand-picked ownership of Commissioner Bud Selig.
At the time, it was expected that they would support the Selig agenda—operating within the financial framework of the small- to mid-market ownership groups across the league. Ownership said all of the right things at the time, espousing the value of re-building the farm system and using the free agent market sparingly to augment its home-grown talent.
But a funny thing happened on the way to the ballpark: the Sox won a world championship... and then, soon thereafter, they won another. With success came a flood of money from attendance, advertising, memorabilia sales, etc. As a result, ownership developed an unquenchable desire to extend its on-field success so that the organization could continue printing money.
The 2004 roster was substantially comprised of players the team had developed (Nomar Garciaparra, Trot Nixon), acquired via trade (Pedro Martinez, Curt Schilling) or some combination thereof (Jason Varitek, Derek Lowe). Most of the free agents on the ballclub were low-cost, high-upside players such as David Ortiz, Bill Mueller, Mark Bellhorn, etc.
The high-priced free agents on the team were inherited, having been signed by GM Dan Duquette while The Yawkey Trust owned the ballclub (notably, Johnny Damon and Manny Ramirez)... the exception was closer Keith Foulke, who had been signed with the blessing of current ownership in the fall of 2003.
The '05 Red Sox were swept in the ALDS by the Chicago White Sox and, soon thereafter, John Henry allowed team president Larry Lucchino to chase GM Theo Epstein from Fenway Park—on Halloween—in a gorilla costume. While Epstein would later returned to the ballclub, the groundwork was laid for an internecine power struggle that would undermine Epstein's sense of security at the top of the baseball operations department.
It had become evident to some of us that ownership had given itself too much credit for the club's success in 2004 and had started meddling where it didn't belong.
The 2006 team missed the postseason all together and, starting in the winter of 2006-07, ownership lost sight of what gave rise to the club's earlier success. The Red Sox became one of the biggest of the big-market teams; they became what we, as Red Sox fans, used to hate about the NY Yankees.
They became part of the problem.
The 2007 roster contained several home-grown players (Ellsbury, Lester, Papelbon, Pedroia, Youkilis) and several of the other key pieces the team had been added via trade (Beckett, Crisp, Lowell), but it had become obvious the migration toward filling needs in The Yankee Way had (sadly) begun: witness the posting fee and contract awarded to Daisuke Matsuzaka and the laughable contracts signed by JD Drew and Julio Lugo that winter.
The '07 club won the World Series, and the '08 team made it all the way to Game 7 of the ALCS, but it appears that success suggested to the owners they had discovered a recipe for success when, in fact, they had stumbled upon a prescription for failure.
While payroll has grown annually and the organization has exceeded the luxury tax threshold in each of the last three (soon to be four) seasons, the Sox have not won a postseason game since '08.
All the while, ownership has lost its focus and grown increasingly clueless... and Henry has grown more and more restless, allowing his focus to drift from the Red Sox. And as that has happened, problems on Yawkey Way have proliferated.
Henry has, at times, been part of the groups that have owned the Orlando Magic, Miami Heat and New Jersey Nets of the NBA. He once attempted to bring an NHL franchise to south Florida. He previously owned MLB's Florida Marlins, but traded up to buy the Red Sox.
Metaphorically speaking, Henry, along with Werner and Lucchino, are carpetbaggers, traveling from city to city on the sports landscape in search of an ownership opportunity.
Aside from his ties to south Florida, where his business has been located since the 1980s, the thing that serves as Henry's primarily motivation is the quest for a good investment and notoriety—and how better to achieve those ends in this day and age than through the ownership of a pro sports team?
At the height of the Red Sox success, he seemingly became bored with baseball... after all, he had broken The Curse of The Bambino. He sought adventure elsewhere, ultimately deciding to dabble in NASCAR with the purchase of a 50-percent stake in Rousch-Fenway Racing (in February '07).
When the Sox won their second World Series in four seasons later that year, his hubris knew no bounds. The second championship only inflamed his thirst for financial and sporting adventure. He began looking for new horizons, eventually finding one across the pond as he and Werner dipped their toes into the world of professional soccer, assuming control of Liverpool FC.
Meanwhile, back on Yawkey Way, the business of baseball had started to unravel.
The organization grasped for success, and as the effort has become more aggressive, it has simultaneously become a sad exercise in futility. Ownership has approved (instigated?) a succession of wasteful expenditures on players, from John Lackey (whose statistics at Fenway Park as a member of the LA Angels were frighteningly bad!) to Mike Cameron, Carl Crawford, Bobby Jenks and Marco Scutaro.
As a result, we all watched in horror as the club suffered the ugliest collapse in history last September; we looked on as ownership chased the GM and manager out of town; and we gasped in horror when Bobby V was introduced as the team's new manager at an embarrassing and farcical press conference.
And as Henry has grown more ambitious in other undertakings and less attentive to the baseball team, the Fenway Follies have become more embarrassing and laughable. Earth to John—time to wake up and smell the coffee!