Regrading Red Sox's Surprising Trade Deadline Deals Two Months Later

Evan Brunell@evanbrunellFeatured ColumnistSeptember 23, 2014

Regrading Red Sox's Surprising Trade Deadline Deals Two Months Later

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    Cespedes has been a run-producer for Boston.
    Cespedes has been a run-producer for Boston.Mitchell Layton/Getty Images

    The Red Sox made some stunning moves at the trade deadline, effectively throwing in the towel on the 2014 season.

    Two months later, it's time to take a look back and see how the deals look like with some hindsight. While the overall evaluations of the moves won't be able to be fully judged until at least after 2015, there's already been some clarity on how the moves will turn out.

    Unlike most teams throwing in the towel and starting a rebuilding effort, Boston focused on acquiring major-league pieces that could help the team turn its fortunes around and pursue a fourth World Series title since 2004 in 2015.

    All in all, the team made four deals at the deadline, shipping out total major-leaguers Stephen Drew, Andrew Miller, John Lackey and Jon Lester.

    A few days prior to the deadline, the club also sent struggling starting pitcher Jake Peavy to the San Francisco Giants. That's worked out wonderfully for the Giants, as Peavy has been an important component of the rotation who has helped vault San Francisco into the playoff race. The team currently occupies the first wild-card slot with Peavy's 2.16 ERA in 10 starts—a large reason for the improvement.

    Boston netted reliever Heath Hembree and starting pitcher Edwin Escobar in the deal, and both have already made their debuts with Boston. If Hembree can become a solid part of the rotation and Escobar can provide depth, this deal will have worked out for Boston quite well.

    Let's take a look at the four deals Boston did after Peavy and grade the impact these moves have had on the team in two months.

Drew Dealt to Yankees:

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    Stephen Drew has struggled for both the Red Sox and Yankees.
    Stephen Drew has struggled for both the Red Sox and Yankees.Alex Goodlett/Getty Images

    Boston Red Sox traded SS Stephen Drew and cash to New York Yankees for 3B Kelly Johnson.

    Stephen Drew is a cautionary tale in turning down a qualifying offer. With draft-pick compensation attached to the shortstop by the Red Sox, Drew couldn't find any deals to his liking in the offseason and eventually agreed to return to Boston for $10 million, the pro-rated amount of the qualifying offer, which was $14.1 million.

    The contract was agreed to on May 21, and Drew made his debut on June 2. 

    Unfortunately, two factors combined to make this deal a terrible decision for Boston. For one, Drew simply could not get his timing down after a delayed start to the season. In 39 games, he hit a measly .176/.255/.328. Further, Drew's arrival pushed 21-year-old Xander Bogaerts to third base. Up until Drew's arrival, the rookie phenom was hitting .296/.389/.427.

    That line started tumbling, and fast, with the move to third. Bogaerts' slump got so bad that even when he was moved back to short with the trade, he couldn't recover until September. From June 2 to Aug. 30, Bogaerts hit a horrifying .153/.201/.234.

    In exchange for jettisoning Drew in order to save money and move Bogaerts back to short, the Red Sox acquired journeyman backup Kelly Johnson. That move alone was valuable just for clearing Drew out.

    Johnson is now with the Orioles, having moved in an August waiver trade along with a prospect to the Orioles for Ivan De Jesus and Jemile Weeks.

    Savvy Red Sox fans will remember that De Jesus is a former Red Sox who came over in the massive August blockbuster with the Dodgers that saw Adrian Gonzalez, Carl Crawford, Josh Beckett and Nick Punto shipped west. It's unlikely De Jesus has a future with the team, but Weeks has received playing time and could compete in spring training for a backup spot.

    While the Drew signing did not work out, we should evaluate this trade based on the fact that Boston saved money, got a poor hitter out of the lineup, opened shortstop back up for Bogaerts and, in the long run, fished out a possible infield backup for 2015. You really cannot ask for more than what the Red Sox managed to extract out of a lifeless Drew.

    And hey, the fact that Drew has actually hit worse with the Yankees (.155/.227/.267), helping them slide out of the postseason race, counts for something.

    Grade: B+

Miller Moved to Orioles:

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    Andrew Miller has been dominant for Baltimore.
    Andrew Miller has been dominant for Baltimore.Rob Carr/Getty Images

    Boston Red Sox traded LHP Andrew Miller to Baltimore Orioles for LHP Eduardo Rodriguez.

    With the Red Sox out of the postseason chase, there was no reason for the team to keep a shutdown lefty poised for the free-agent market. 

    After being the No. 6 pick of the 2006 draft, a major centerpiece of the deal that sent Miguel Cabrera to Detroit, Boston picked Miller up off the scrap heap and worked him into a dominating reliever. In three seasons of relief, he has posted a 2.53 ERA with 13.6 strikeouts per nine innings over 131 2/3 frames.

    The 29-year-old has been especially dominant in 2014, and the Red Sox were able to spin him into Baltimore's No. 3 prospect, ranked so prior to the season by Baseball America.

    Rodriguez had a scant 0.96 ERA in six starts for Double-A Portland after coming over and appears ticketed for Triple-A in 2015. ESPN's Keith Law called Rodriguez the best prospect to get traded on trade-deadline day and believes he could be a mid-rotation option for the Red Sox shortly.

    Giving up around 20 innings of August and September relief appearances by Miller (who has 18 1/3 to date with Baltimore) for a prospect who could be a mid-rotation starter in a year or two is an obvious win.

    Grade: A

Lackey Heads to Cardinals:

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    John Lackey's Cardinals career has not gone as planned.
    John Lackey's Cardinals career has not gone as planned.Dilip Vishwanat/Getty Images

    Boston Red Sox traded RHP John Lackey, LHP Corey Littrell and cash to St. Louis Cardinals for RF Allen Craig and RHP Joe Kelly.

    This deal is the hardest of the four deadline deals to evaluate.

    On one hand, the Red Sox jettisoned a pitcher whowhas having an excellent season for the Red Sox, his second in a row. Lackey had a 3.60 ERA through 21 starts prior to being moved and was functioning as the No. 2 starter. In addition, Boston held a club option for the league minimum on Lackey for the 2015 season.

    However, there was some speculation Lackey would refuse to pitch for the league minimum with Boston, as D.J. Short of NBC Sports reports. With Lackey's future in Boston cloudy, the Red Sox opted to move the mercurial right-hander for a bat and a replacement starting pitcher.

    It was only this past October that Craig was hitting in the middle of the order for the Cardinals in the World Series against the Red Sox. Due to a Lisfranc injury in his foot, however, Craig has struggled majorly in 2014 in what has shaped up to be a lost year with a cumulative .218/.283/.322 line for two clubs.

    Craig could still pay dividends on the deal. The Cardinals sold Craig and the three years left on his contract at a discount because of his struggles. It's entirely possible that with an entire offseason to rest the foot and get his timing back, Craig could become a middle-of-the-order threat again—the ability to play first base, the outfield corners and third base.

    Don't discount Craig manning the hot corner for Boston, as the Boston Herald reports that the team has had internal discussions about moving the 30-year-old there in 2015.

    Meanwhile, Kelly has been essentially the same pitcher he was for the Cardinals: striking out just enough to keep pitchers honest but also walking a bit too much. However, his ground ball tendencies have allowed him to stay effective, with a quality infield behind him gobbling up outs.

    As ESPN Boston's Gordon Edes writes, "The Sox like his big arm and his above-average changeup. They see an improving curveball and command. They hope he settles into the middle of [the] rotation."

    Meanwhile, in St. Louis, Lackey has struggled to the tune of a 4.50 ERA in nine starts.

    Next season is going to crystallize what grade this deal truly deserves, but for now there's nothing to like or dislike about it.

    Grade: C+

Blockbuster Ships Lester to Oakland:

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    The A's have struggled, but not because of Jon Lester.
    The A's have struggled, but not because of Jon Lester.Jonathan Daniel/Getty Images

    Boston Red Sox traded LHP Jon Lester, LF Jonny Gomes and cash to Oakland Athletics for LF Yoenis Cespedes and No. 2 pick in Competitive Balance Compensation Round B.

    While Yoenis Cespedes hasn't lived up to the production he was racking up in Oakland, the Cuban has still been well worth giving up Jon Lester.

    After Sunday's game, Cespedes is three RBIs away from driving in 100 runs in a season for the first time in his career. Hitting a combined .258/.300/.455 on the year in 146 games, he'll never be mistaken for someone who will be a discerning eye at the plate, but he brings something else to the game that is increasingly rare: right-handed power.

    The addition of Cespedes to the middle of the order has dramatically lengthened the lineup. The 28-year-old will form a dangerous core of the lineup in 2015, the final season he is under contract.

    In addition to Cespedes, the team also received the No. 2 pick in the competitive balance compensation round B, which is held after the second round. The 12 available picks are distributed to teams that are in small markets or have small revenue pools, and these teams are allowed to trade those picks, as MLB.com's Teddy Cahill explains.

    Not only does the additional pick give the Red Sox the opportunity to draft a second well-regarded player, the bonus slot that comes with the pick will be added to Boston's total slot pool. This is a big commodity in the game these days because teams are able to exceed bonuses for pick slots, but cannot exceed the total value of the slot pool.

    In theory, the addition of this pick could enable the Red Sox to pick someone in the draft, signing them to an over-slot deal and walking away with a better player as a result.

    Of course, this trade cost the Red Sox their ace in Jon Lester, who spent 13 seasons with the Red Sox and the last nine in the major leagues. While losing Lester is a big blow that removed a frontline pitcher from the rotation, it was increasingly clear to all concerned that it was extremely unlikely that Lester would resign with the Red Sox on a team-friendly deal.

    Whether or not the Red Sox were at fault for such an outcome is a debate for another day. This trade evaluation is based on whether they got enough value for Lester in return. The 30-year-old has come up aces for Oakland despite their slide, posting a 2.20 ERA over 10 starts.

    It can be debated whether the club should have gone the prospect route over hauling in Cespedes, but 10 years from now, this deal could look markedly different when we know the results of the draft and whether the Red Sox drafted their next great player with the pick. 

    In the end, Boston took a player who was sure to hit the free-agent market and likely to leave and turned him into a power-hitting commodity and a draft pick. Plus, Boston could conceivably resign Lester in free agency. All in all, there's not a lot to dislike here.

    Grade: B