From the very beginning, his exit was merely an eventuality. Theo Epstein would one day no longer be the Red Sox General Manager.
When he was first selected by the Red Sox ownership group in 2002, Epstein became the youngest GM in Major League history. With the success that soon followed, he was widely viewed as a baseball wunderkind.
When your team plays in two consecutive League Championship Series and wins a World Series during your first three years on the job, that happens.
Additionally, when you win two World Series in a four-year span, and appear in four League Championships Series in a six-year span, people tend to see you as a baseball savant.
However, the reality is that Epstein inherited a 93-win Red Sox team from former GM Dan Duquette. The roster Epstein inherited had a host a talent, including Nomar Garciaparra, Manny Ramirez, Johnny Damon, Pedro Martinez, Tim Wakefield, Jason Varitek, and Derek Lowe.
Duquette had drafted Garciaparra, Kevin Youkilis, David Eckstein, Adam Everett, Hanley Ramirez, and Freddy Sanchez, leaving the Red Sox farm system well-stocked.
That enabled the Sox to make a major deal with the Marlins in 2005, swapping Hanley Ramirez for pitcher Josh Beckett and third baseman Mike Lowell. That deal essentially won the Sox the 2007 World Series championship.
Duquette’s performance as GM was solid. His big-ticket acquisitions - Martinez and Ramirez - worked out well.
The same cannot be said of Epstein.
While Epstein struck pay dirt with low cost, under-the-radar free agent acquisitions like Bill Meuller, Kevin Millar and David Ortiz, his tenure with the Sox was also marred by a series of high-priced busts.
John Lackey, Bobby Jenks, Mike Cameron, JD Drew, Daisuke Matsuzaka, Julio Lugo, Matt Clement and Edgar Renteria were all disappointments or outright busts.
And while the Carl Crawford experiment is still incomplete, it's clear that his previous accomplishments with the Rays never warranted such a massive long term deal in the first place.
During his years as the Red Sox GM, Epstein also made an assortment of trades, with mixed success.
Without question, the highlight was the acquisition of Curt Schilling for Casey Fossum, Brandon Lyon and two minor league pitchers. Obviously, that proved to be a shrewd move and it benefitted the Red Sox immensely.
But many trades orchestrated by Epstein proved regrettable.
In 2003, Epstein traded away Freddy Sanchez — an eventual batting champion and All-Star — for righthander Jeff Suppan.
Suppan, a journeyman who had come up with the Red Sox in 1995, had a career ERA of 5.51 when Epstein acquired him. True to form, Suppan posted a 3-4 record and a 5.57 ERA upon his return. His performance was so miserable that the Red Sox gladly let the free agent walk away that offseason.
Trading for Coco Crisp never worked out as projected either, especially since Crisp was chosen over Johnny Damon.
Epstein reportedly offered Damon a four-year contract valued at $40 million and refused to match the Yankees four-year, $52 million offer. That was clearly a regrettable decision. Damon had four very productive seasons with the Yankees and won a World Series title with New York.
Epstein has long admitted that trading Bronson Arroyo for Willy Mo Pena was a big mistake. Pena has bounced back and forth between the minors and majors, and from organization to organization, ever since. However, no other GM seemed nearly as enchanted by Pena's power potential as Epstein was.
Meanwhile, all Arroyo has done is win 79 games over six seasons with the Reds, throwing a minimum of 199 innings in each of them.
One of Epstein's best decisions as GM was the trade of Garciaparra, who had become a malcontent in Boston. In exchange, the Red Sox received Doug Mientkiewicz and Orlando Cabrera, the later of whom proved to be a real spark for the Sox down the stretch and in the playoffs.
However, despite Cabrera's boundless energy, enthusiasm and popularity with teammates and fans alike, Epstein chose not to offer him a free agent contract after the 2004 season, opting for Renteria instead. That move proved to be a double-whammy for the Sox, in which they lost twice with just one bad decision by their GM.
Epstein also struck out with his lamentable decision to trade for closer Eric Gagné at the deadline in 2007. As a result of the Mitchell Report, it is now known that Epstein had been coveting Gagné since the previous offseason.
In a November 2006 email exchange, Epstein questioned Red Sox scout Marc Del Piano about the possible acquisition of the then free agent closer. In the email, Epstein asked DelPiano, "Have you done any digging on Gagne? I know the Dodgers think he was a steroid guy. Maybe so. What do you hear on his medical?"
DelPiano replied that "steroids IS the issue" with Gagné, questioned his "poise and commitment" and expressed questions about his durability "without steroid help."
Despite the reservations expressed by Delpiano, Epstein still traded Kason Gabbard and minor league outfielders David Murphy and Engel Beltré to the Texas Rangers for Gagné on July 31, 2007.
Gagné was an unmitigated disaster in Boston, posting a 6.75 ERA over 20 games, which led to him being kept off the post-season roster.
Murphy, meanwhile, has been a starting outfielder for Texas ever since and has now represented the Rangers in two consecutive World Series.
Lastly, Epstein also traded Justin Masterson (plus minor league pitchers Nick Hagadone and Bryan Price) to the Indians for Victor Martinez. However, Martinez played with the Red Sox for just eight months before leaving via free agency.
Now that Martinez is gone, the Red Sox have nothing to show for the loss of Masterson, who has emerged as one of the better young starters in the AL. The big righty posted a 3.21 ERA in 2011, while tossing 216 innings for Cleveland.
Meanwhile, the Indians have Masterson, who is only arbitration eligible, under their control for the next two seasons at a low cost.
It must also be noted that part of Epstein's legacy is assembling a clubhouse full of coddled, overindulged millionaires.
Terry Francona was known as a player's manager. However, it now seems that such a disposition will no longer work in the entitled environment of the Red Sox clubhouse. That said, Francona was not the problem; he was merely a symptom.
This is Theo's team; it was his creation. He built this squad of rich, spoiled, prima donnas.
But it seems that Francona did indeed lose his clubhouse, and he knew it.
Jim Rice said the Red Sox clubhouse was a "spa." On their off-days, pitchers were said to be drinking beer there during games, instead of rooting on their teammates from the dugout.
There were reports of cliques among the pitchers, of resentment among teammates, of a culture of entitlement, of complacency. Apparently the pitchers, particularly the starters, rarely spoke to position players and that created a gulf in the clubhouse.
Remember the old "25 cabs for 25 players" Red Sox? Well, they're back.
Players were out of shape and lacked conditioning; that's just unprofessional. The only regular players who routinely showed up for optional batting practice were Dustin Pedroia and Jarrod Saltalamacchia.
The Red Sox were a team divided.
Yet, many are sorry to see Francona go. That's understandable since he was such a likable man. In many ways, Francona seems like the fall guy for Epstein's mistakes. But the Sox now need a true General to get the players in line, and they need to lose a few players too — starting with John Lackey.
However, almost as quickly as this season was over, Lackey has already been lost — but perhaps not for good. Sitting out the 2012 season due to Tommy John surgery will essentially make lackey untradable. And he'll have to prove himself in 2013 before any team might even consider taking on that risk.
Epstein knew about existing issues with Lackey's elbow, yet still handed him a massive, five-year, $82.5 million contract anyway. It was for this reason that the Red Sox had language inserted in the pact assuring that if Lackey lost significant time due to this pre-existing elbow issue, the Red Sox could have him for the league minimum in a sixth year.
How's that sound, Red Sox fans? Looking forward to John Lackey, year-six, yet?
As Red Sox GM, Epstein was the beneficiary of the second or third highest payroll in baseball virtually every year he was at the helm. That money was not always well-spent.
While Red Sox ownership can be rightfully criticized for being distracted by its ventures into Roush Racing and Liverpool soccer, it must also be credited for providing the financial resources to field a very competitive team each and every year. And it is not a meddling ownership; it has let its baseball operations people do their jobs without interference.
For better or worse, Epstein's organizational philosophy will remain largely intact with the passing of the torch to his minion, Ben Cherington. Over the past decade, the Red Sox have done a laudable job a drafting and player development.
The one hiccup was the lack of a big league-ready starter when one was suddenly needed this season. The hole in the pitching-development chain suddenly appeared gaping. Naturally, this hole will close with time.
Yet, it doesn't appear that the Sox have a single minor league pitcher currently ready to step in and make a meaningful contribution in 2012 — at least not out of the gate. However, that may change in a year, or so.
Sadly, one thing that didn't change on Eptein's watch was the Red Sox' long, sorry history of players leaving the team on bad terms: Nomar, Pedro, Damon, Manny, Jason Bay; who knows who will be next? That's a shame. However, Damon aside, management has mostly made good calls in letting its free agents walk.
The bottom line is that Theo didn't build the 2004 team as much as he inherited it. Even the acquisitions of Beckett and Lowell, so instrumental to the 2007 Championship, were not Epstein's doing. In fact, he was said to be so in love with Hanley Ramirez that many believe he wouldn't have consummated that trade.
The Red Sox reign is not over. Epstein's reign is over, as is Francona's. The organization is bigger than any GM or any manager. Every tenure must eventually end. The fact that Epstein lasted nine years and Francona eight is remarkable in modern pro sports.
They endured because the team was mostly enjoying success over that span.
However, Francona lost control of the team and Epstein made some very poor free agent / trade decisions that the club is still living with and paying for.
Too many Red Sox players are spoiled, lazy and entitled. New leadership is needed.
It's difficult to tell how different Cherington will be; after all he was groomed by Epstein and served as his right hand man for so many years. The drafting and development philosophies will likely remain the same, but free agent evaluation needs to improve markedly.
Cherington inherits a team that now has a recent history of winning and is no longer burdened by 1918. The Sox are a historic franchise and a marquee team. The new management team will have an enormous payroll at their disposal and top-notch scouting and development resources.
The Red Sox are also a team with a record sellout streak still intact and huge TV revenues. This is a prime opportunity for any management team.
While the Sox recent successes led to the pressure of great expectations, the team Epstein inherited faced even bigger expectations; they hadn't won it all in 84 years.
And let's face it; every team faces pressure and expectations. Defeat quickly gets old for everyone. If you continually lose (like the Pirates), you also lose your fan base and your revenues, meaning you can't recruit top free agents.
In Boston, there is certainly the pressure of fielding a competitive team, a winning team. But could there possibly be any more pressure now than in the decades leading up to 2004?
This team needs the new leadership it is getting. They will be fine.
However, the Red Sox do face lots of moving parts this offseason; David Ortiz, Jonathan Papelbon, Jason Varitek, Tim Wakefield, etc.
Kevin Youkilis has one year left on his deal. How does he factor into whether or not the Sox re-sign Ortiz? What trade value does Youk have after breaking down in consecutive seasons?
Who is the right fielder? Who are the fourth and fifth starters?
There are lots and lots of questions.
Most immediately, the Red Sox need a skipper who will act like a General and restore order from chaos. And that General will need a pitching coach to be his Colonel. Some asses need to be kicked, and perhaps some players need to be kicked out.
The Red Sox players have lost sight of how good they have it compared to the rest of society. They've forgotten how everyone else lives. They travel first class. They stay at first class hotels. They are paid in the millions annually — even the tens of millions. They get a per diem on the road and have huge spreads in the clubhouse every day. They get adulation and adoration.
And they feel entitled to all of it. That has to change.
More than anyone else, Theo Epstein is responsible for this culture. He assembled this team, not Terry Francona. And for that, Epstein must take the blame.
This is the immediate legacy he has now passed on to Ben Cherington.
