2014 in 8 Days: Top Red Sox Moments

(Photo by Charles Krupa/AP Photo)

by Dakota Antelman

The long and the short is that 2014 did not treat the Boston Red Sox too kindly.

They went 71-91 in their second season under John Farrell and failed to execute in any of the ways that helped them win a World Series a year ago. Their outfield was weak and much of the left side of the infield began showing signs of mechanical fatigue. 

The Boston bats died in 2014 and as injury reports ran manically through the rows of Fenway and the heads of fans, our lovely defending champions wallowed in a season of despair and mediocrity.

Thus is it no secret that this year's top Red Sox stories all took place off the field...

1) Jon Lester chooses Cubs over Red Sox

After low-balling Lester with a meager $70M contract offer back in Spring Training the longtime Red Sox ace was somewhat irked by the team. Further adding to the perceived lack of respect by the team for Lester was the fact that midway through the season they traded him to the Oakland A's.

That move made it easier for Lester to ignore the "hometown discount" when the negotiation period rolled around this off-season. It was with ease that he turned down a $135M offer from the Red Sox, signing instead a monstrous $155M offer from the suddenly invested Chicago Cubs just last month.

2) Red Sox unload at trade deadline

It cannot be stressed how much the trade that moved Lester out of Boston for the first time effected the negotiations after the season as well as the remaining games in the season.

On July 31st, Lester and charismatic outfeilder Johnny Gomes were packaged in a blockbuster deal to the Oakland A's. The Red Sox got two time home run derby winner, Yoenis Cespedes in return.

At the time the deal seemed somewhat decent as Cespedes brought with him a mega bat and at least an average glove in left field. As they unloaded their pitching though, the Red Sox were soon caught in a vicious cycle of blowouts and games gone to the bullpen by the 4th inning.

John Lackey, Jake Peavy and Felix Dubront were all sent packing at the trade deadline. The players they got in return, though promising did little in the second half of the season and at times began to raise some questions about Ben Cherrington's leadership scheme.

3) Red Sox ink $200M in contracts in one morning

In a time where those questions about Cherrington's ability were burning brightest, the GM jumped into the rebuilding phase quickly and with both feet.

Looking to remedy some run scoring problems from last season, Cherrington dished out $200M in contract money to sluggers Pablo Sandoval and Hanley Ramirez. The deals spawned immense questions about how the team would deal with the two in terms of their defense.

As it finally shook out, team sources suggested to multiple media outlets that Ramirez would spend time in center field and bat in the top of the order. Sandoval would be the starting third basemen for the Red Sox, effectively ending Will Middlebrooks tenure with the team as he did so. (Middlebrooks was traded just a few weeks after the Sandoval/Ramirez signings.)

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Red Sox Rework Pitching Staff at Winter Meetings

(Photo courtesy of the AP)

by Dakota Antelman

Immediately after Jon Lester alerted the Red Sox of his decision not to sign the contract they offered him, the team moved on to other options. Within 36 hours of that call they had completely reworked their pitching staff, adding multiple starters and thinning out their bull pen.

In the final days of this week’s baseball Winter Meetings, Boston traded Yoenis Cespedes to the Tigers in exchange for Rick Porcello. They soon after signed free agent pitcher Justin Masterson to a one year $9.5M deal and, late Friday night, completed a trade with the Diamond Backs that shipped Wade Miley to Boston in exchange for Ruby De La Rosa, Allen Webster and a minor leaguer with single-A Lowell named Raymel Flores.

"We've been able to acquire the three starters that we have this week while still maintaining what we consider the top end of our young pitching, and still have what we think is really good, young pitching depth beyond the five guys that will likely begin the season in the rotation,” said Red Sox GM Ben Cherrington.

The team was aware of the need to remedy the inconsistency and detrimentally fluid nature of their pitching order going into this offseason. The additions made this week reflect a desire to do just that.

But as it stands, there remain quite a few discrepancies between this staff and an ideal one. Namely, despite their depth, the staff made up of Clay Buchholz, Joe Kelly, Porcello, Masterson and Miley has no clear ace.

Cherrington however does not see that as a problem.

“Once Opening Day is gone the whole No. 1 starter thing kind of is overrated," he said. "Whoever takes the ball that night, it's his responsibility to help us win and pitch every five days, so the order really doesn't mean as much once you get past Opening Day. We feel like we have a rotation now that can help us win every game."

Of the current pitchers, one thing that does seem certain is that, at least for the first few games, Masterson will likely sit towards the bottom of the pitching order. He had the worst statistical season last year of the recent newcomers and has shown a propensity in recent years to go down early with nagging injuries.

On the other end of the spectrum, Porcello could very well become a favorite of his coaches as, since joining the league in 2009, he has averaged nearly 6 innings of play per start.

Drawing out long starts has been a quality that the Red Sox have openly looked for in their pitchers this offseason. Porcello’s ability to play Lester like innings bodes well for him especially within the Red Sox system. Even former pitching coach and current manager John Farrell commented on the value of a 200 inning pitcher like Porcello.

“Ideally, if you can get a couple of 200-inning pitchers -- they don’t grow on trees, but that’s the goal,” Farrell said generally on the subject of pitching depth.

As the 2015 Red Sox roster begins to take shape, the pitching staff folds and molds into what the fan base and the coaches alike all want it to become. Depth is a necessity but at the same time, practicality is crucial. Jon Lester did not return to Boston because $155M was not a practical salary for Boston to give him. Max Scherzer will likely not come to Boston for similar reasons.

But that is not to say that depth cannot be built in other ways. The Red Sox have boosted their pitching staff with veteran talent that promises to compliment the young arms they have maturing down in Pawtucket. That makes them attractive to free agents young and old. Furthermore, the surplus of hitters and outfielders that they have gives the Sox plenty of shots in the trade market. They might soon attempt to track down guys like Phillies ace Cole Hammels, former Red Sox prospect Anibel Sanchez, or Reds star Johnny Cueto.

“There are some quality options that still remain on the pitching market,” Farrell said. “Ben’s working hard to build out a pitching staff that’s going to put us in a position to contend next year. We firmly believe that will take place.”

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Jon Lester signs with Chicago Cubs, solicits mixed emotions from Bostonians

Early Wednesday morning, sought after free agent ace, Jon Lester signed a 6 year $155M contract with the Chicago Cubs choosing them in favor of his former team, the Red Sox.

After months of deliberations, meetings, offers and false reports, a 30 year old Lester became the fourth highest paid player in baseball with his blockbuster contract. The deal, which will run through the 2020 season, involves a $30M signing bonus spread out over the contract and a yearly base salary that will not change from season to season. At the end of year six of the contract, the Cubs will either have the option to invoke a $10M buyout on Lester or a $25M vesting option in the event that he pitches 200 or more innings in 2020.

Among the other contractual courtships that the Cubs contract grants Lester are a guaranteed 25 hours of personal flying time on a private jet each calendar year and a no trade clause.

The $170M that the Cubs contract makes available to Lester was enough to make the Red Sox offer appear obsolete and halfhearted to many fans.

The final offer from Boston (while not as definitely fleshed out details wise as the actual deal Lester signed) appeared to have clocked in at $135M. Furthermore, it lacked the no trade clause that Lester, a family oriented man, has expressed desire to have.

While Lester has said many times over that he would be willing to take a hometown discount, the $20M discrepancy between the Boston and Chicago contracts in guaranteed money seemed to be too much.

He needed more from Boston if he was to return.

In the end though, the Red Sox were simply unwilling to dish out that extra mouney especially after committing nearly $200M to Hanley Ramirez and Pablo Sandoval last month.

"We had a pretty clear idea internally where we were willing to go in the offseason and we had an opportunity to go there," GM, Ben Cherington said. "What we didn't know is where the market would go. In free agency there's always a chance the market gets past where that line is. In this case it did."

The official signing at 1AM Wednesday and the Tuesday night call to management that preceded it signified a somewhat awkward end to a nine year career in Boston that won Lester two World Series rings.

Following it, there was budding animosity felt by Sox fans towards the greater debacle of the past month. Among the poster children for that anger were and still are the faces atop the Red Sox managerial ladder.

Going back to last spring, the team seemed to show apparent disrespect towards their long tenured ace. They offered him multiple small money contracts that were at times over $50-70M less than the one he just signed. As he rejected each contract, they vilified him in their interactions with the media almost attempting to portray him as someone less than the professional that he was.

The damage done in the preseason seemed to hurt the Red Sox’ chances with Lester as the team and him entered the negotiation process.

But at the same time, such rationalization for the departure of a Boston legend could be overthought.

Rather, Lester, a possible future hall of famer, a man who had already won a pair of Championships, a three time all-star and a resilient man who beat deadly cancer of the blood years ago could very well have gone to the team that offered him the money he deserved.

Jon Lester loves Boston. But the Cubs are willing to love Lester. And even if they bought his love, Lester will likely pitch as good or better than he did last season. In doing so, he will instantly make the Cubs a team, infinitely better than the one they fielded a year ago.

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Red Sox meet with Pablo Sandoval, discuss potential contracts

November 18th, 2014

by Dakota Antelman

Members of the Red Sox front office met with sought after free agent Pablo Sandoval for several hours Tuesday afternoon. They invited the 3^rd basemen to see Fenway Park before meeting in team offices to discuss potential deals.

The Red Sox have expressed interest in Sandoval since mid-August as they noted his contract terminating after this past season. The interest in Sandoval stems mainly from his being a powerful switch hitter.

He hit 16 home runs last season and would be one of the Red Sox only left handed hitters if he was signed.

Beyond offensive versatility, Sandoval would provide a kind of consistency at third base that has been lacking in recent years. He put up a .971 fielding percentage a year ago and initiated 27 double plays. If signed the Sox would likely plug Sandoval in as a full time third basemen for next season.

Also, if Sandoval were to be given the six year term that he requests be part of his contract, he would be with the team long enough to be considered as a replacement for David Ortiz as designated hitter when he retires.

Sandoval would without a doubt better the Red Sox as a baseball team but he is currently commanding a very large paycheck.

During today’s meetings, baseball reporter Jerry Crasnick tweeted that sources had told him that Sandoval has verbalized his desire to sign within the ballpark of $80-$90 million over six years. He later suggested that a deal with Sandoval could materialize very quickly.

Despite that, conflicting reports exist that insist that there is little or no chance that a contract actually gets drawn up and agreed upon before Sandoval leaves town later this week.

But regardless, the Red Sox acted on their promise to go “all in” on Sandoval. They did so with a ball park tour, a short experience of Boston, and a reported dinner Tuesday night. The Red Sox seem to be giving Sandoval all available options in an attempt to lure him onto their roster.

"It's an opportunity for (players) to ask questions," Red Sox GM Ben Cherrington said of these recruiting meetings in general. "These are choices, big decisions that free agents make. Obviously, a big piece of it is going to be the economics. But it's a life decision and they should get an opportunity to ask questions about whatever they want to ask questions about.”

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Thoughts on Koji Uehara contract extention: Sox should be wary of thin line they are walking

November 2nd, 2014

by Dakota Antelman

Earlier this week the Red Sox managed to ink a two year 18 million dollar deal with their closer, Koji Uehara. Uehara who, especially in 2013, exhibited near hall of fame talent from his position, will likely end his career making $9 million a season. Needless to say, nine million dollars is a hefty price to pay for a player in his final professional seasons.  Whether or not it is a worthy price will be proven by Koji’s play throughout this contract.

Uehara has been in baseball for over two decades now. He came to the MLB having already amassed a particularly impressive career with Japan’s Yurimori Giants baseball team and soon did the same in America. He played three years with Baltimore and two seasons with Texas. During that span, Uehara was only given the role of closer once and rarely even made it into games.

With Boston, that all changed. Since he came to the team in the onslaught of transactions that preceded the 2013 season, he has made 47 saves and blown just 8. His ERA has averaged out at just about 1.8 while his ability to utterly humiliate batters has never been overlooked.

"You're really looking at a guy who has been one of the elite relievers in baseball for several years," Red Sox general manager Ben Cherington said.

But after all, Uehara also was at times shaky this season giving rise to the question; was 2013 just a fluke?

Furthermore when you compare Uehara’s deal to those of some of the MLB’s other top closers its values could worry some Sox fans.

For example, Tiger’s closer Joe Nathan was given a $20 million dollar contract before this past season. By the numbers his contract is similar to that of Uehara. However Nathan was handed the pay raise after a 43 save season in which he amassed an ERA of 1.39. Those numbers are not similar to those of Uehara.

The Sox appeared to have evaluated the play of Uehara intensively but it also appears that they may have not reached the best final decision. Very frankly, giving a 39 year old such a big money contract after he was admittedly “shaky” could very well hurt this team in the near future.

Koji Uehara is a very talented player but the Sox are showing some blatant inconsistencies in their personnel decisions. If they saw enough problems in their closer’s game to bench him than they should not then turn around and claim to see enough good things in his game to pay him such a big contract.

The Boston Red Sox are walking a dangerously thin line here.

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Rusney Castillo praised for professionalism, confidence in MLB debut

Red Sox fans were finally treated to the long awaited debut of Cuban star Rusney Castillo Tuesday night.

Ever since the team signed the 27 year old outfielder to a whopping 72 million dollar contract last month, fans had been eagerly awaiting their first chance to see the star in a big league game. Castillo was said to be the kind of player that could play a huge role in this franchise going forward and fans were excited to see if that was true. And yet ever since Castillo’s ETA to the MLB was announced last week, Red Sox fans had been further weighed down by the question that seems to always go hand in hand with these kinds of contracts. What if? Sox fans asked ahead of his debut, what if we overestimated him?

Those worries were an omnipresent emotion that seemed to crawl in between the questions, tweets and predictions fired off as the prospect of Castillo’s debut drew closer and closer to its becoming a reality.  

As a result, PNC Park in Pittsburgh was packed to capacity Wednesday playing host to journalists, Pirates fans and Red Sox fans alike, the majority of whom were there to see Castillo. Their able bodied, able talented subject of their showering in anxious admiration did not disappoint. Needless to say, he did not shock fans either.

Playing 8 innings out in left field, Castillo made just one play on the baseball, snagging an easy put out in the 5^th innings. At the plate, he went 1-4 logging his first career hit in the 4^thinning on a sharply hit grounder to second base.

1 hit is not spectacular but judging by the fact that that 1 hit was struck during the biggest game of Castillo’s career, he has no reason to hang his head; and he is not.

"I'm pretty satisfied with that being my first game; obviously you would like a better outcome in terms of winning the game, but I was pretty satisfied with my overall approach and the way I stepped in today and had some results," Castillo said to translator Adrian Lorenzo after the game.

Castillo has shown that he has the skills to step in and made a big impact on this team once he builds some chemistry with the staff and his teammates. He said Wednesday that he feels he is in a good place as a ball player.

"Yes, yes, I've been pretty happy with the way things have worked out, not just with the success on the field but the relationships I've been able to develop with the coaching staff and clubhouse staff and teammates." He said.

In a lost season that sees the Red Sox on pace to finish with virtually the same record as they did two years ago under Bobby Valentine, Rusney Castillo is quickly showing both adaptability and sheer skill in his new club. After playing with poise and a cool head Wednesday, this player deemed worth 72 million dollars by his coaches is winning immense praise from those coaches and GM’s.

Ben Cherrington, the mastermind behind the August deal for Castillo was among the most impressed with Castillo’s professionalism.

"I don't think it's the results that you learn from. It's just watching him around the team, pregame, interacting with people, questions he asks, all that stuff has been positive so far,” Cherrington said. “Even if you just start with the time he was in Miami, and the showcase and go from there, the signing, the minors, being in Fort Myers, Portland, Pawtucket, he's met a lot of people and played games in a lot of different places, and he's handled it all well."

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Ryan Dempster walks away from 14 million dollar contract with the Sox: How long term fatigue finally caught up to Dempster and ended his up and down MLB carrer

15 years after he first joined the league, 40,000 pitches after the first one he threw one, 5 teams after he was drafted by the Rangers in 1995, Ryan Dempster is stepping away from this game that has been his for a decade and a half.

Fact is nobody expected this. Even though he might likely be booted from a starting role mid-season and would make his biggest contributions to this team as a periodically penciled in middle reliever, Dempster still had almost 30 million dollars in contract money to be paid out to him over the next 2 years. That number alone would have made most stick around. But that is not what Ryan Dempster did. Frankly, you have to hand it to him for having this kind of assertiveness in knowing what is best for himself and his family.

In the 15 years since his first contract was paid out, Dempster has made close to 90 million dollars and has in 12 seasons posted an ERA above 4.5. It would be fair to say that Dempster has never performed with the excellence that his money most surely demands. And yet at the same time, if you subtract him from the 2013 Red Sox roster that won the World Series last year, a pretty decent void would be left wide open. While when you take into account the money Dempster was paid last year, each of his 8 wins cost the team about 1.6 million dollars, he was not all that bad especially towards the end of the season.

After starting the year an abysmal 2-6, Dempster turned things around going 6-3 in his final 9 decisions of the year. Those 6 strong victories included key outings in both Chicago and Detroit towards the end of the year when the Sox were competing tooth and nail with the Oakland A's for the number one seed in the AL. But come playoff time it was clear that compared to John Lackey, Jon Lester, Clay Bucholz or even Jake Peavy, Dempster was nothing more than a side note and so he was confined to the bullpen for all of October. There he made 3 appearances (1 in each series) and at least in the first two was not half bad allowing just 2 hits a combined 18 pitches. 

The 3rd of those outings of course came in Game 1 of the World Series where Dempster blew a shutout by allowing a home run and 1 hit after that in the 8th inning of an 8-0 game.  

Honestly, that probably did not cause Dempster to much mental strife. Having played 597 games in the sport of professional baseball, Dempster has most surly had his low points and so he knows how to deal with them. But at the same time those 597 games have also spawned hundreds of bright spots that take to form of the 132 wins Dempster has led whatever team pays him to. Twice he has been an all-star and in 5 postseason games, he has grabbed the ball.    

But he is tired. 

"But I just feel like where I'm at with my health, how I feel personally, I just feel like it's in the best interests of both myself and the organization and the team to not play this year. I don't feel like I can compete or produce the way I'm accustomed to." Dempster said. 

According to Red Sox GM, Ben Cherrington, part of Dempster's decision to leave had to do with a nagging neck injury that he could not seem to shake. 

"Talking to Ryan, even before he came down here today, there were mixed emotions on his part," Farrell said. "He's had a great career. You congratulate him on that, but I think when the end is nearing [and] ... the physical side of things take away from the performance, you empathize with that and know you can't go on and play this game forever." 

Additionally, from what we have heard from the entire Red Sox organization since Dempster retired, though he was not necessarily the best pitcher on this roster, he was one of the most liked as his humble but humorous personality made it so that both Cherrington and John Farrel were sad to see him go. 

"In a career full of earning respect and building respect, he's ending his time with the Red Sox in a way [winning the World Series] that only bolsters that, strengthens that feeling about him," Cherington said. "It was ultimately the right thing to do in his mind. That doesn't mean it was an easy thing to do, and I have great respect for him making the decision that way."

Over 15 years these things, no matter how thrilling begin to take a toll on your body and while he has never been a man prone to injury, Ryan Dempster is a classy player who knows when it is time to call these up and down years in baseball a career. That time is now.  

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