What's next for the Red Sox after the trade deadline?

Even now, it's hard to wrap your head around all of the moves the Red Sox made at the trade deadline. All of a sudden, nearly half of the team that won the World Series in 2013 is practically gone and instead replaced with a group of fresh faces aimed towards future success. It's as if someone decided to create a new franchise in MLB 14 The Show, hit the fantasy draft mode and recreated the Red Sox.

Gone are four main players from the championship squad: Jon Lester, John Lackey, Jonny Gomes and Stephen Drew. In return, the Red Sox received new faces including Yoenis Cespedes, Allen Craig, Joe Kelly, Eduardo Rodriguez, and Kelly Johnson. The deadline was the busiest in franchise history and the day, as a whole, was one of the most significant day of transactions in Major League Baseball.

That being said, it's clear what the message from Ben Cherington and the front office is: the plan is to reload for 2015. Instead of a crop of prospects that could potentially affect the team two, maybe three years down the line, Cherington brought in a group of players with the mindset that the team could compete again as early as next year.

It is clear, however, that the moves on Thursday have serious ramifications for the team beyond 2014.

Jon Lester's contract situation

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While the trade of Jon Lester is clearly a result of the team and the big lefty being unable to come to an agreement on a long-term contract, Cherington would not comment on whether or not Thursday's trade ruled out a potential return for the lefty to the Red Sox in the offseason.

"€œHe’€™s an Oakland A right now, so I don’€™t think it’€™s right for me to talk about that other than to say looking back that we certainly had a desire to engage on a contract conversation with him," Cherington said. "That conversation just didn’€™t happen enough for whatever reason. As we got deeper into the season he made it clear that that wasn’€™t something that he wanted to focus on right now and so we honored his desire. And we had conversation with Jon about that, that we respected that position but because of the performance of the team that meant that we both might have to deal with this possibility."

Cherington says the team will cross the bridge of potentially bringing Lester back if the opportunity presents itself.

"So what happens,€“ that’€™s not for me to talk about now," Cherington said. "He’€™s an Oakland A and he’€™s got a job to do for them. When we get to the offseason we get to the offseason."

An exhausted Cherington, who did not sleep the night before the deadline, said that trading Lester was the toughest decision of his front office career.

"€œIt is difficult and it catches you at a different moment," Cherington said. "Last week, when things started not to go well in the Toronto series and then going into Tampa, I knew that the more the math built against us, the more possibility there was to have to face some of this. Tough decisions with people that have meant a lot to the Red Sox and who I’€™ve known for a long time and have done great things for the organization."

The future of Xander Bogaerts, the shortstop

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It's hard to find anything that went right with Stephen Drew's second year with the Red Sox. Not only did Drew struggle to do much of anything at the plate, but the struggles of Xander Bogaerts coincided with his move to third base. While it's important to consider that correlation does not equal causation in regards Bogaerts' move to third, the shortstop was incredibly happy when he was told that he would be playing shortstop for the rest of the year, news broken to him via a phone call from manager John Farrell, according to a source familiar with the situation.

Given that the Red Sox have next to no chance of making the playoffs, the focus for Cherington was the push towards the future. Cherington and company need to know whether or not Bogaerts can play the shortstop position moving forward. Before the Drew signing, third base coach Brian Butterfield expressed great optimism and hope regarding Bogaerts' progression defensively at the shortstop position. Many believed that Bogaerts was trending in the right direction and on a good path towards becoming, at the very least, an average big league shortstop defensively.

Despite Bogaerts' struggles over the last two months, the view of the 21-year-old has not shifted in the front office.

"He’€™s going to be a really good player for us for a long time," Cherington said. "We said last winter we believed he can play short for us — that didn’€™t change because we signed Stephen Drew despite the attention around it. We signed Stephen Drew because we were trying to fill a need at a time that we were still trying to win and claw for wins. In retrospect, that move didn’€™t work out the way we wanted it to."

The final two months of the season will be crucial for the future of Bogaerts and could ultimately determine where on the field he ends up playing for the rest of his career. Regardless of the position he plays in the field, Bogaerts has impressed the staff with his work ethic and his focus on the day-to-day grind of the baseball season.

"In the long run, I don’€™t worry about Xander Bogaerts because he’€™s going to be good," Cherington said. "He’€™s going through stuff but he’€™s going to be good. He’€™ll have to go back to shortstop and take ground balls there now. It looked like he was even getting more comfortable at short right before he moved to third so hopefully he’€™ll just pick right up where he left off."

Bogaerts will likely share the left side of the infield with Will Middlebrooks, who Cherington announced will be activated before Friday's series opener against the New York Yankees. The final two months will likely play a huge role in what the team decides to do with their third baseman overload. Garin Cecchini, who has struggled at the plate in Triple-A this year, is still in the picture moving forward at third base, despite his experiments with the outfield in Pawtucket.

The future of the rotation

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Clay Buchholz, yes that Clay Buchholz, is currently the pitcher on the Red Sox pitching staff that holds the most major league experience and it's really not even close. In the views of many, Buchholz is not an ace pitcher. Speaking at his Buchholz Bowl charity event on Thursday, Buchholz didn't seem to view himself as much of a leader yet either.

"I feel good where I'm at right now," Buchholz said when asked if he could lead the pitching staff. "I feel healthy and obviously, the numbers haven't gone the way that I wanted it to this season yet, but if I have 10, 11, 12 starts left, I'm going to go out there and treat it like it's another game and go out and try to do the best I can to help the team win."

While it's easy to rag on Buchholz for not viewing himself as a leader, it's important to point out (as Marc Normandin shrewdly did to me) that Lester did not always view himself as an ace. Lester early in his career had a crutch in the form of Josh Beckett, someone he could lean on. It was not until 2013 that Lester truly asserted himself as a leader on the Red Sox and took on that leadership role for the pitching staff (uncoincidentally the year after the team traded Beckett to the Dodgers in the Nick Punto trade).

With all things considered, the Red Sox rotation's age scale is heavily tilted towards the mid-20's. Cherington and company will have the opportunity to evaluate what the team has with the group of young pitching prospects. The team currently has nearly ten pitchers that will/could make an impact at the major league level in 2015. Such pitchers include Allen Webster, Rubby De La Rosa, Brandon Workman, Anthony Ranaudo, Matt Barnes, Henry Owens, Edwin Escobar, Eduardo Martinez and Brian Johnson.

€œ"Obviously some of those young pitchers are going to get a lot of opportunity the rest of the way ‘€“ the guys that are already here," Cherington said. "Ranaudo is going to start [Friday] night. We have an opportunity to watch that and they have an opportunity to pitch and develop. We’€™ll know a lot more about that group by the end of the season and that will help inform us, to some degree, going into the offseason. It would be my expectation that we would be active no matter what happens the rest of the way."

The influx of young pitching gives the team flexibility to go out and make a move in the offseason (I promise, I won't mention He-Who-Must-Not-Be-Named or the guy whose name rhymes with Shmancarlo Shmanton). Had Cherington not traded Lester (and hypothetically lost him in the offseason), he would have had to use prospects, the organization's greatest strength, and money to add both a power-hitting outfielder and a top-of-the-rotation pitcher. By trading Lester for Cespedes, Cherington uses his most valuable to get an outfielder that will immediately contribute this and next year while maintaining prospect depth to go after the next great Red Sox ace.

"My expectation is that we would be active in the starting pitching market this winter with trades, free agency, whatever," Cherington said. "But we’€™re going to learn a lot more about our young group. We liked our young group of starters two weeks ago and now we’€™ve added a couple more to that in Escobar and Rodriguez, two young starters we got. We feel very good about the depth of young starters that we have in the organization. Obviously they’€™re not proven major league pitchers and so we’€™ve got to learn more about them the rest of the way and see what’€™s available to us this winter."

As for Kelly, the righty represents a pitcher under team control who has flashes of good stuff.

"If we were going to do it, we really prioritized getting major league players, but then in particular at last one starting pitcher back, and in Kelly we feel like we have a guy who is on the come and is a developing, advancing major league starting pitcher," Cherington said. "Certainly not a finished product, but really talented,€“ someone our scouts have liked for a long time. Highly athletic, really good stuff and we feel someone who can quickly develop into a core part of our rotation. So he was an important addition as we go into the offseason. We wouldn’€™t have done the Lackey deal without getting someone like that back.€"

The future of the outfield

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The area of the Red Sox that most clearly got a big boost was the outfield. The addition of Yoenis Cespedes and Allen Craig immediately makes the Red Sox outfield crowded. At the moment, the team has a total of seven players who can man the green grasses of Fenway Park: Cespedes, Craig, Shane Victorino, Jackie Bradley Jr., Daniel Nava, Mike Carp and Brock Holt.

Cherington made clear that Cespedes would man right field -- a position where the 28-year-old has no experience -- and that Craig would roam in left field. That, logically, would misplace Nava, who could serve as part of a platoon in left, despite Craig's even splits against right-handed and left-handed pitching, Victorino, who Cherington hinted would be placed on the disabled list due to recurrent back issues, and seemingly eliminate any need of Carp, whose services as a backup first baseman may not be needed with Craig and Holt's abilities to man the position.

"We are not writing anything in stone where that goes in the future, but we’€™d like to get both guys acclimated in that way," Cherington said. "We will see where we are."

Cespedes and Bradley represent two of the strongest outfield arms in baseball. No word yet if the two will face off in a throw off for the ages yet.

Cherington takes the hit

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For the second time in his three-year tenure as the Red Sox general manager, Ben Cherington hit the reset button. Cherington clearly expressed disappointment in the team's position at this point in the year.

"We'€™re in this position because of the performance of the team and the performance of the team is ultimately my responsibility," Cherington said. "If we had done a better job as an organization this year and performed better then it'€™s not just likely but obvious that most of this stuff would not have happened today. So you have to start there, I have to start there with the acknowledgement that if we weren'€™t in the position that we'€™re in, which I take responsibility for, then these trades don'€™t happen. And we don'€™t want to be in that position. We take responsibility, the performance on the field hasn'€™t been good and certainly not good enough."

While time will ultimately tell if Cherington can strike magic again, he is proud of the job that ownership, baseball operations and Farrell did during the trade deadline.

"I think we'€™re in better position than we were a week ago, but certainly not done," Cherington said. "Obviously now that the deadline has passed there'€™s likely a lot less activity as far as roster moves the rest of the way other than I'€™m sure at some point some young players will come up. Hopefully we'€™ve done things to get a head start on the offseason, address some things, but I think, and I know John [Farrell] feels the same way, we'€™ve got 54 games left.

"These are now the most important 54 games of our season because we'€™ve got a lot to find out. We have new players that we want to make sure are comfortable and get acclimated to Boston and comfortable at the ballpark and everything that comes along with Boston. We'€™ve got young players who are still developing and need to continue to improve and develop, we need to focus on that. And we need to start building a team again so a lot of the guys that are now on this roster will more than likely be on the roster next April so we'€™ve got to start building a team that can win. So I think the next 54 games are really important toward that. But of course, there'€™ll be more work to do this offseason, too."

So what's next?

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What this trade deadline showed, more than ever, is that anything can happen. Just yesterday, there was no mention that Yoenis Cespedes could even be an option for Jon Lester until the trade was going down. Who knew that the Red Sox could get Joe Kelly and Allen Craig for John Lackey?

This is important to note because the next great Red Sox ace could be someone that nobody is even considering right now. Sure, James Shields, Max Scherzer and Jon Lester are all free agents who are top-of-the-line starting pitchers, but Cherington could be loading up on assets to make a deal that nobody will see coming.

It's been clear for a while now that the 2014 iteration of the Red Sox weren't going anywhere. Ben Cherington did the right thing in aggressively shopping any pieces that had value and getting a return that will immediately improve the team's chances of winning in 2015. Given the team's seemingly unlimited assets, Cherington will most definitely continue to improve his team heading into next season.

What he does next, however, is anybody's guess.