A quiet day would be an abnormal development for the Red Sox, who are usually active at the deadline, especially since the turn of the century as they’ve consistently made major moves to either boost a playoff-caliber team, or tear apart the bad ones. Many deals succeeded, leading to championship runs. Some failed miserably. Others, well, didn’t do much of anything. Regardless, Theo Epstein, Ben Cherington and Co. were never afraid to pull the trigger.

Today’s trade deadline may leave Red Sox fans underwhelmed, but many deadlines haven’t. Let’s look back at some of those busier deadlines and see just how well (or poorly) they turned out. I present you with the five biggest Red Sox trade deadlines of the 21st century.

5.) 2013

Red Sox acquire right-handers Jake Peavy and Brayan Villarreal, send shortstop Jose Iglesias to the Tigers and send right-handers J.B. Wendelken and Francelis Montas to the White Sox

This trade technically came the day before the 2013 trade deadline, but I make the rules here, and I say that’s good enough to make this list. Anyway, the 2013 Red Sox were in the midst of a worst-to-first turnaround, but needed another starting pitcher for their playoff push. Insert Jake Peavy. The righty gave the Sox just what they needed, posting a 3.82 FIP in 10 regular-season starts and helping them win the World Series. Peavy’s 2013 postseason was less than stellar, but he did start the ALDS clincher against the Rays, allowing just one run on five hits over 5.2 innings. The Red Sox got an ok half season out of Peavy in 2014 before shipping him to the eventual world champion Giants in 2014.

The only notable loss for the Red Sox in that deal was Jose Iglesias, but even his departure wasn’t a major letdown at the time with Stephen Drew and Dustin Pedroia at shortstop and second base, respectively, Will Middlebrooks (sort of) contributing at third and Xander Bogaerts on his way. Iglesias was known primarily for his glove coming through the Sox organization, but was hitting well early on in 2013, posting a .285 TAv in 63 games before being dealt. Iglesias missed all of 2014, owned a .252 TAv in 2015 and has a .243 TAv this season. Meanwhile, Bogaerts could be the one of the best offensive shortstops in the majors for years to come. Safe to say the Red Sox made the right move.

Iglesias still contributed to the 2013 title, by the way.

That led to this:

4.) 2009

Red Sox acquire catcher Victor Martinez from the Indians for right-hander Justin Masterson, left-hander Nick Hagadone and catcher Bryan Price

The playoff-bound Red Sox bolstered their lineup with one big swap, adding Victor Martinez in exchange for Justin Masterson and a pair of prospects. Martinez proved to be a nice addition, as he split time between catcher and first base over 183 regular-season games between 2009 and 2010. Martinez posted a .302 TAv in 237 plate appearances in 2009 and a .281 mark the next year. He didn’t give the Red Sox the postseason production they were hoping for in 2009, collecting just a pair of hits, but that run also lasted just three games.

This trade wasn’t necessarily a win or loss for either team, but it’s safe to say the Indians got more out of the deal. Masterson pitched five solid years in Cleveland, his best being in 2013 when he was the ace of the staff and led the Indians to a postseason berth with a 2.63 DRA and 3.38 FIP. The righty’s career has since flamed out after a disastrous season with the Red Sox in 2015, but the Indians certainly got the best of him.

3.) 2014

Red Sox trade left-hander Jon Lester to the A’s for Yoenis Cespedes and a competitive balance pick; send right-hander John Lackey and left-hander Corey Littrell to the Cardinals for outfielder Allen Craig and right-hander Joe Kelly; trade left-hander Andrew Miller to the Orioles for right-hander Eduardo Rodriguez and send shortstop Stephen Drew to the Yankees for utility infielder Kelly Johnson

Making one major trade at the deadline is big. Two deals is impressive. Four deals in one day is on another level. That’s exactly what the Red Sox did at the 2014 trade deadline as they shipped off a number of veterans over four trades, eyeing the future in the midst of a last-place season.

The Sox’s deadline activity actually began five days earlier when they traded Peavy to the Giants for Heath Hembree and Edwin Escobar. Escobar is no longer with the team, but Hembree has turned into a nice innings eater out of the bullpen. The real fireworks, however, began early on the morning of the deadline when Jon Lester was sent to the A’s for Yoenis Cespedes. Lester was once again pitching like a top-of-the-rotation starter, but the Sox were out of contention and the lefty was in the final year of his contract with no long-term agreement in sight. Cespedes, meanwhile, was a big bat with another year left on his deal. Lester picked up where he left off upon joining the A’s, posting a 2.35 ERA and 3.16 FIP over 11 starts. The Sox pursued Lester in the offseason, but lost out to the Cubs. Cespedes owned a .269 TAv over 213 plate appearances before being dealt to Detroit for Rick Porcello in the offseason. Sure, Porcello doesn’t seem like a stellar return for Lester (although Porcello has been one of their two most dependable starters this season), but they also could have lost the lefty for nothing that offseason had they not traded him.

Then there was the deal we’d all like to forget. That was the deal that brought Allen Craig and Joe Kelly to Boston in exchange for John Lackey. The trade made plenty of sense at the time. Lackey was pitching well, but had little future left in Boston, especially after expressing his displeasure about pitching at the major-league minimum in 2015. Craig was a former All-Star who appeared to be simply having a bad year, while Kelly was young, could throw hard and had shown potential after posting a 2.69 ERA over 15 starts in 2013. Two years later, the deal looks as bad as ever for the Red Sox. Lackey posted a 2.77 ERA while pitching at the minimum for the Cardinals last season. Craig spent most of last season in Triple-A and has since fallen off the face of the earth. Kelly has spent his time with the Red Sox either hurt, or bouncing between Triple-A and the majors.

As dominant as Andrew Miller has been over the last two-plus years, a young pitcher like Eduardo Rodriguez was about the best you were going to get for a rental reliever (how times have changed). The Orioles got the most out of Miller, who owned a 1.16 FIP in 23 appearances with Baltimore in 2014. He’s since become one of the best closers in baseball over the past two seasons. The Red Sox, meanwhile, got a potential middle-of-the-rotation arm for a player they would probably lose to free agency anyway.

The Stephen Drew trade proved to be insignificant. He gave the Yankees an ok season and a half and Kelly Johnson gave the Red Sox next to nothing. However, the trade opened up shortstop for Bogaerts, and we all know how that’s gone.

This deadline was as crazy as it gets for any team. At the time, the Red Sox seemingly won the day, but hindsight shows that not all of it worked out as planned. The Lackey deal is a perfect example of that. However, it would’ve looked worse if the Red Sox lost some of these players to free agency.

2.) 2008

Red Sox acquire outfielder Jason Bay from the Pirates, trade outfielder Manny Ramirez to the Dodgers and send right-hander Craig Hansen and outfielder Brandon Moss to the Pirates

This trade was years in the making. It was far from the first time Manny Ramirez had been part of a trade rumor, and even further from the first time he wanted out of Boston. In 2008, the Red Sox finally pulled the trigger, and got a player in Jason Bay who could fill Ramirez’s void immediately. From a straight trade standpoint, the Red Sox and Dodgers both got solid production for a year and a half of service. Bay posted a .308 TAv in 211 plate appearances with the Sox in 2008, while owning a .302 mark the next season. Ramirez was even more impressive with his .425 TAv in 229 plate appearances with the Dodgers in 2008 and .336 mark in 2009 as LA reached the NLCS both seasons. Ramirez was clearly better than Bay during that time, but by that point he had been nothing but a distraction in Boston and needed to go.

As for the prospects the Red Sox gave up. Craig Hansen’s career continued to be forgettable. Brandon Moss’ career never really materialized until his 2012 arrival in Oakland in 2012, where he totaled 76 home runs over three seasons. Moss, 32, has a .323 TAv and 17 home runs for the Cardinals this season.

1.) 2004

Red Sox acquire shortstop Orlando Cabrera from the Expos and first baseman Doug Mientkiewicz from the Twins, and send shortstop Nomar Garciaparra and outfielder Matt Murton to the Cubs, and acquire outfielder Dave Roberts from the Dodgers for outfielder Henri Stanley

This may go down as the biggest trade deadline in Red Sox history. It was significant enough that they traded, at the time, one of the most iconic players in team history. Add in the fact that it helped propel the Sox to their first World Series title in 86 years and you’re talking about a deadline worth telling your grandkids about.

We start, of course, with the Nomar Garciaparra trade. Garciaparra had been the face of the Red Sox since his 6.0 WARP rookie season in 1997 and a clear fan favorite. He was also really, really good, owning a 43.7 WARP between 1997 and 2003 (keep in mind he missed most of 2001). But by July 2004, he had seemingly overstayed his welcome in Boston. He was in a contract year with no promise of returning, had become a defensive liability and was expected to miss more time with an Achilles injury. Epstein, in a stroke of groinal fortitude, dealt away the superstar in hopes of shoring up the team’s “fatal flaw”: defense.

Epstein got just what he was looking for from Orlando Cabrera. The shortstop’s .268 TAv with the Red Sox was comparable to Garciaparra’s .272 TAv with the Sox in 2004, but he also posted a positive FRAA and played 15 more games than Garciaparra did in the final two months. Cabrera left at the end of the season and the Red Sox began a carousel at shortstop over the next decade, but the championship and Garciaparra’s rapid decline soon after was enough to justify the move.

The Dave Roberts trade was a footnote in the midst of an active deadline, and with good reason. The outfielder made just 101 plate appearances and posted a .251 TAv. He was simply acquired to add speed, defense and depth off the bench. However, Roberts is also responsible for the biggest stolen base in Red Sox history.

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It’s unlikely the Red Sox will do anything to top these trade deadlines this season. But that’s why a list like this exists. You don’t get fireworks every season. When you consider the moves the Sox have made in the past month, it makes even more sense for this deadline to be a quiet one. That’s not always a bad thing.

 Photo by USA Today Sports Images

Let’s go over those transactions, what the thoughts were behind them (presumably) and how that thinking may have changed 10 months later.

July 26

Trade 1: Jake Peavy and cash to the San Francisco Giants; Received Edwin Escobar and Heath Hembree

Who Boston Gave Up: At the time of the deal Peavy was struggling with a 4.72 ERA. Of course as soon as he got to the Giants he became peak Peavy again, throwing 78 innings of 2.17 ERA ball, but that doesn’t matter to Boston. Good for Peavy, who won his second ring in as many years with the Giants and netted himself a two-year, $23 million deal to stay in San Francisco. He wasn’t needed in Boston anymore.

Who Boston Received: What matters here is that Escobar and Hembree came to Boston for half a season (what was remaining on Peavy’s deal at the time) of an older pitcher who wasn’t pitching well. Escobar, the get in this deal, just turned 23 years old. He’s a lefty with some speed on his fastball, two average off-speed pitches, and the potential to step into the back or, if everything breaks right, middle of a major league rotation sometime in the near future. His upside is about what the Red Sox gave up in Peavy (not the Cy Young Peavy, but the Red Sox version), but with seven years of control at a low cost instead of three months at a high cost. Right now he’s on the disabled list with left shoulder inflammation, which does not sound good, but then that’s the life of a pitcher.

The other player in the deal was Heath Hembree. The scouting report was that he has a fastball that reaches the mid-90s, but not a whole lot else, but he’s doing quite well in Triple-A this season with 12 strikeouts to only two walks in 12.1 innings.

Utterly Arbitrary Grade: It’s unclear how the careers of the two pitchers who came to Boston will play out, but as with all young pitchers, the Red Sox got themselves two lottery cards and, at least in one instance, a card with decent odds of turning into something. Even in light of Peavy’s success with the Giants this deal looks like a steal. A.

July 30

Trade 2: Felix Doubront to the Chicago Cubs; Received a player to be named later ( Marco Hernandez)

I’m going to skip the boilerplate and just say that Marco Hernandez has a .610 OPS in Double-A as a 22-year-old. Further I’m going to say Felix Doubront, after a short required post-Red Sox tour of duty with the Cubs, was released and as of this writing is out of baseball. Generally I don’t like deals where one club deals a major leaguer for a minor league nobody. Even if the major leaguer is not very good, he’s still a major leaguer, but in this case, this is effectively nobody for nobody. Moving on…

July 31

Trade 3: Traded Andrew Miller to the Baltimore Orioles; Received Eduardo Rodriguez

Who Boston Gave Up: At the time of the deal Miller was one of the best relievers in baseball. Now, he’s one of the best relievers in baseball. That’s a tough standard to maintain, though. In 2014, Miller was worth 2.2 fWAR, seventh-best in baseball among relievers. Care to guess who was the seventh best reliever in baseball by the same metric in 2010? Matt Belsile. Sure it would be nice had the Red Sox re-signed Miller, but given who he is and what they got, it’s still a deal you make every time from Boston’s position.

Who Boston Received: Eduardo, or Eddie, Rodriguez, came as a highly touted 21-year-old starter, one of the best prospects in Baltimore’s system. But he wasn’t supposed to be this good. Upon getting to Pawtucket, he altered the way he threw his changeup and took off from there, crushing the International League through the end of the 2014 season. This season he’s picked up mostly where he left off.

Utterly Arbitrary Grade: This is exactly the kind of deal an out-of-contention team should make. Exactly. The fact that the Red Sox netted their best pitching prospect helps the optics of it, but even if Rodriguez blew out his arm tomorrow, a high upside starter for half a season of a reliever, even one as good as Miller, is a no-brainer. Sure it would be nice had the Red Sox re-signed Miller, but given who he is and what they got, it’s still a deal you make every time from Boston’s position. A

Trade 4: Traded Stephen Drew and cash to the New York Yankees; Received Kelly Johnson

Again no boilerplate here. This one was pretty simple, if notable because of the organizations involved. The Red Sox had re-signed Drew to play shortstop on a contender. They were not a contender, thus they didn’t need Drew. The Yankees needed someone to play second base while they chased a Wild Card. Without Drew the Yankees didn’t need Kelly Johnson. The Red Sox, as it turned out, didn’t need him either, flipping him to Baltimore for Jemile Weeks and Ivan De Jesus at the end of August. De Jesus was cut loose and is now in the Reds organization while Weeks is (not hitting) in Pawtucket.

The end result here was the Red Sox didn’t have to pay the last two months of Drew’s contract. Mission accomplished!

Trade 5: Traded John Lackey, Corey Littrell, and cash to the St. Louis Cardinals; Received Allen Craig and Joe Kelly

Who Boston Gave Up: John Lackey had a year and a half of his contract left when Boston sent him to St. Louis. Due to a clause in his contract that specified he would play an additional year at the major league minimum if he missed a year with an arm injury, Lackey was a steal. The Red Sox had Lackey, a number two or three starter, at about $600,000, for a full season. That’s value right there, and the front office should have extracted value in return. They… sort of… did?

Who Boston Received: There was talk of receiving a top prospect but the Red Sox went a different route, opting for major league-ready players in return. They got, as you know, Joe Kelly and Allen Craig.

We’ll start with Craig. Clearly a buy-low attempt by the front office, the former All Star had received MVP votes in two seasons prior to suffering a Lisfranc injury that essentially wrecked his 2014 season. The hope was an offseason of recovery would do wonders and the Red Sox would have an All Star on a long-term, low-cost deal. So far, at least, this has not happened, and it has not happened in a profound way. Craig has been horrendous, batting .130/.235/.192 during his time with Boston. The problem is that if Craig isn’t hitting he doesn’t bring value on defense or on the bases, and he’s not especially great at getting on base either.

The Red Sox sent him to Pawtucket. His career isn’t over. There is still a chance to salvage some value here, but just the fact that I’m using the word “salvage” should make it clear how badly this part of the deal has gone. At this point the Red Sox couldn’t give Craig away, let alone trade him for something valuable like a year of a good starting pitcher.

Then there’s Joe Kelly. Kelly may or may not be a starting pitcher. There’s a case to be made that he’s pitched much better than his ERA shows, he’s young, he’s got a woof’n fastball, and he’s under team control until 2019. Those are all points in his favor. And even if he’s a bullpen arm, he’s got some value. One could make a case that Kelly is worth a season and a half of Lackey. I’m not sure it’s a case I’d make for this team as currently constructed, but you could construct an argument that wouldn’t be nuts.

Utterly Arbitrary Grade: It’s important to note that the Red Sox received nine player seasons for a year and a half of Lackey. Right now they have six plus of those player seasons remaining. The returns aren’t promising, but there is still time. D

Trade 6: Traded Jonny Gomes, Jon Lester and cash to the Oakland Athletics. Received Yoenis Cespedes and 2015 competitive balance round B pick

Who Boston Gave Up: We’ll dispense with Gomes because this isn’t about him in any way at all. The Red Sox season was over and he had no more usefulness left. This is all about Jon Lester, the best pitcher the Red Sox have developed since Roger Clemens. I’m not going to rehash all the contract negotiations here, but in the end the Red Sox determined they couldn’t meet Lester’s price. Then, during the off-season, they attempted to meet Lester’s price, which by that time had gone up. I’m shaking my head right now. I consider myself an objective analyst but it is admittedly difficult to be objective about this. Given where Lester was in his career, you can maybe understand why the Red Sox made the offer they did. But by the time the trade deadline rolled around the team had succeeded in poisoning the well to such an extent that they felt they couldn’t sign Lester. We now know with some certainty that had they come to Lester on that day and offered him the six year, $135 million deal or even a slightly lesser variant of the same deal they would present to him in three months, Lester would still be in Boston.

This would be a whole lot easier to stomach if the Red Sox didn’t need Lester but of the holes on this current team, the biggest is at the front of the starting rotation. Losing Lester means the team better have received something hugely intensely amazing in return…

aaaaaaaaaaaand they didn’t.

Who Boston Received: Yoenis Cespedes was and is a good power-hitting outfielder who the Red Sox might have thought they could sign long term. They couldn’t agree on terms and Cespedes was dealt to Detroit for Rick Porcello, who the team then gave the money they initially offered to Jon Lester to. Porcello should do fine for Boston but unless he develops new strikeout skills, he’s not the pitcher Lester was.

By the letter of the law, the Red Sox turned a half season of Jon Lester into a season and a half of Rick Porcello, plus exclusive negotiation rights that turned into a four-year extension. Yet it’s difficult to look at it that way. Lester wanted to stay in Boston. The Red Sox needed him to stay in Boston. He should still be in Boston. But he isn’t, and it’s hard to look at that as anything other than a huge mistake.

Utterly Arbitrary Grade: I really wanted to give this an F, but Porcello is a good pitcher and an asset, no matter what you think of his contract. C-/D+

The focus on major league players was an attempt to bolster the roster for a playoff run in the short term. Plainly put, that part has not worked. Craig and Kelly are disappointments or non-factors, and it’s not hard to see that the team would be better off with Lackey. Porcello is, again, fine, but he’s a step or two back from Lester. The fact that Craig is now in Triple-A adds an ironic twist to Boston’s insistence on bringing back major league players in these deals, as well as a sad statement on their lack of success. Oddly, the player who may present the largest impact to the major league team might be Eduardo Rodriguez.

Boston’s strategy appeared to be similar to how some teams (most teams?) approach the draft: accumulate as much talent as possible regardless of position and let things sort themselves out later. The Red Sox did that to some extent by acquiring Cespedes and then flipping him to Detroit for Porcello. Beyond that, Boston may have under-estimated their ability to upgrade the offense through free agency during the then coming off-season. If they knew adding Pablo Sandoval and Hanley Ramirez were possibilities it makes you wonder why they’d want Allen Craig.

The story of the 2014 deadline deals isn’t over. We won’t know for a long time how this whole thing plays out. But right now, 10 months after the fact, with holes throughout the rotation and an overabundance of money if not talent committed to the outfield, it’s difficult to call those six days successful.

Top photo by Bob DeChiara/USA Today Sports Images

If we’re looking for admiration, we have to step back one season prior to 2013, when a championship appeared as if Ben Cherington just happened to find one in the bottom of his back pocket while taking a post-lunch stroll through the Common. Not unlike the 2004 squad, the 2013 team dissolved almost as quickly as it emerged. Some have retired, some have remained, but many have scattered, ashes from an urn, floating on the winds to new destinations where, they hope, the cycle will be repeated.

For us now, we have the 2015 team and the hope and promise they bring, but as we focus on our new friends, perhaps it is worth a look back on old friends to see how they’re making out. What follows is a series of questions intended to test your knowledge of the 2013 team, the World Series, and what those players who brought you the third World Series win in the last 10 seasons at the time have done since.

1. Two years later, what percentage of the 2013 team remains on Boston’s roster?
A) 33%
B) 50 %
C) 67%
D) 75%
E) 82 %

2. Which member of the 2013 team has been the most valuable player by WARP since winning the World Series (so including 2014 and 2015)?
A) Jacoby Ellsbury
B) Dustin Pedroia
C) Jon Lester
D) John Lackey
E) Jarrod Saltalamacchia

3. Which pitcher other than Jon Lester and John Lackey won a 2013 World Series game?
A) Jake Peavy
B) Felix Doubront
C) Brandon Workman
D) Junichi Tazawa
E) Ryan Dempster

4. Which member of the 2013 team has played for the most teams since hoisting the World Series trophy?
A) Felix Doubront
B) Stephen Drew
C) Andrew Bailey
D) Franklin Morales
E) Alfredo Aceves

5. Which former Red Sox’s new team is doing the best in the standings so far in 2015?
A) Andrew Miller
B) Jonny Gomes
C) Jarrod Saltalamacchia
D) David Ross
E) Jose Iglesias

6. After David Ortiz’s .688 batting average, the next highest for a Red Sox player during the World Series was .250. Who did that?
A) Dustin Pedroia
B) Xander Bogaerts
C) Daniel Nava
D) Jonny Gomes
E) Jacoby Ellsbury

7. Which member of the 2013 Red Sox left the team in 2014 only to return to the organization this season?

8. Which member of the 2013 Red Sox has been the least valuable by WARP this season?
A) Jon Lester
B) Jonny Gomes
C) Andrew Miller
D) Jarrod Saltalamacchia
E) Stephen Drew

9. Of the now moved on 2013 Red Sox, who put up the best OPS+ in 2013?
A) Jarrod Saltalamacchia
B) Stephen Drew
C) Jonny Gomes
D) Will Middlebrooks
E) Jose Iglesias

10. Of the now moved on 2013 Red Sox, who has the most home runs this season?
A) Jarrod Saltalamacchia
B) Stephen Drew
C) Jonny Gomes
D) David Ross
E) Jose Iglesias

Click here for the answers!

Photo by Kelly O’Connor, sittingstill.smugmug.com