Boston’s pick in the fifth round of the 2011 draft has, by Baseball Reference WAR, out-produced every player taken in the first round of that same draft. That would be Mookie Betts.

Partly that’s a function of the fact the Red Sox have been a better team than the Orioles over that time. Thus when Baltimore has picked it has more often been at the top of the draft where more is expected to come of the selection, whereas the Red Sox have often picked later where star power is much harder to come by.

But even then, the Red Sox have still done better than Baltimore. There are probably other teams that have done better than the Red Sox over the past three decades (going much deeper into draft history is pointless as the draft has changed so much since) but though they exist they likely aren’t many. Take for example, Boston’s pick in the fifth round of the 2011 draft has, by Baseball Reference WAR, out-produced every player taken in the first round of that same draft. That would be Mookie Betts, and that would be amazing.

Of course, that’s not the only time the Red Sox have had a non-first round pick and (to date) got more production out of it than any of the first rounders used that in that same draft. They did it in 2004 when they used the 65th overall pick to take Dustin Pedroia. If you want to hold this exercise to just the first round though, well, even then the Red Sox have done well. The following draft, 2005, the Red Sox had the 23rd pick as compensation for Orlando Cabrera signing with the Angels. They used it on outfielder Jacoby Ellsbury, the sixth most valuable player (B-R WAR) taken in that draft.

So the Red Sox have scored when they should’ve scored and scored when they probably shouldn’t have scored. But they haven’t always nailed it. In 2010, they used the 20th overall pick on Kolbrin Vitek with Christian Yelich taken three picks later. Vitek never made it above Double-A, retiring four years after being picked. Even so though, the 20th pick isn’t a surefire star waiting to happen. That’s more like a guy you’d hope could turn into a solid contributor. Vitek never was that (why he’s mentioned in this paragraph!) but missing out on the 20th overall pick isn’t something to quit over. Oddly enough, current Red Sox star pitcher Chris Sale was selected seven picks earlier, but I digress.

The real problem, as the Orioles can attest to, is getting a top-ten pick and blowing it on nothing. The Red Sox haven’t officially done that yet, but it’s pretty close. Trey Ball has a 5.53 ERA in Double-A and is looking less like a future rotation cornerstone and more like a guy who gets dropped in the end of an insubstantial trade, or even converted to the outfield because why not? Worse, Boston took Ball with a bunch of still promising guys available (Austin Meadows, JP Crawford, Hunter Dozier, Christian Arroyo, Aaron Judge), though that’s how every draft is. There’s always someone promising available. The trick is knowing who it is.

You have to go pretty far back to find so high a pick go so badly for the Red Sox. In 1995 the Red Sox took pitcher Andy Yount two picks before Roy Halladay went to the Blue Jays, but that was with the 15th overall pick, not the seventh. In 1994 Boston took Nomar Garciaparra with the 12th pick, and in ’93 they took Trot Nixon with the seventh pick. Hard to complain about either, even if Nixon didn’t ever quite live up to the star power that was projected upon him.

Since Theo Epstein took over the GM’s seat in early 2003 the Red Sox have been incredibly good at getting value out of the draft. It’s hard to win three World Series in fifteen years without getting something substantial from the draft. The Red Sox built the foundation of their first World Series winning team through trades and free agency, but their second, the 2007 team came far more from the draft. While there were ’04 crossovers in Jason Varitek and David Ortiz, and free agents like J.D. Drew and Julio Lugo, the ’07 team was also Kevin Youkilis, Jacoby Ellsbury, Dustin Pedroia, Jon Lester, and Jonathan Papelbon. The 2013 team was similar in its composition. Lots of free agents and players acquired in trades, but with a solid core of home grown players like Lester, Pedroia, Felix Doubront, Clay Buchholz, Will Middlebrooks, and Ellsbury, with assists from Xander Bogaerts and even Jackie Bradley.

Looking at that 2013 squad, you can still see the roots stretching back to Theo Epstein and Boston’s first world championship in almost a century, but so can you see the future, or as we here in 2017 say, the present. The Red Sox don’t owe it all to the draft. They’re not the Rays or the Astros, but the draft has provided the Red Sox with a lot of value and a sizable amount of star power over the past few decades. So when going to look for Boston’s biggest draft busts or some such thing, you’ll have to be searching for a long time. Or, put more succinctly, the Red Sox aren’t the Orioles. Because when it comes to the draft, the Red Sox are hobgood at it.

Photo by Eric Hartline – USA TODAY Sports

Beltre’s 2010 was a breakthrough after five middling seasons in Seattle. He emerged as a top-tier player who was a strong fielder and could hit for power. He was a legitimate star on a mediocre team lacking in star power (or, according to Tom Werner, sexiness). An impending free agent, Beltre positioned himself for a nice payday in the offseason.

It seemed clear the Sox wouldn’t be the ones to pay him. Beltre was 31 years old and, like many players before him, excelled in a contract year. The Red Sox would receive two compensation picks if he signed elsewhere. Letting Beltre, who was not a lock to match his 2010 numbers again, walk in exchange for a pair of picks in what was expected to be a deep draft looked like the obvious choice.

So that’s what the Sox did. Beltre signed a five-year, $96 million deal with the Rangers. The Red Sox moved Kevin Youkilis to third and traded for All-Star first baseman Adrian Gonzalez. Boston later used its compensation picks to draft outfielder Jackie Bradley Jr. and catcher Blake Swihart, both of whom had the makings of top prospects. The Red Sox were World Series favorites and their future was solidified.

The Red Sox lost a player whose production hardly wavered over the duration of his next contract — in fact, Beltre has been one of the best third basemen in baseball over that span — and the Sox in return were one of the worst teams at third base.

But did they make the right decision?

Hindsight is a funny thing. We as writers and fans use it as a tool to reflect on a team’s past decisions. In most cases the answer is pretty explicit. However, in this situation hindsight paints a fuzzy picture even five years later. On one end, the Sox lost a player whose production hardly wavered over the duration of his next contract — in fact, Beltre has been one of the best third basemen in baseball over that span — and the Sox in return were one of the worst teams at third base.

But by moving on Boston has acquired a pair of young players with the potential to be mainstays for the coming years. Bradley is one of the most exciting outfielders the team has produced in recent memory, and despite inconsistencies has shown he can be a dangerous hitter when hot. Swihart came into 2015 as the team’s top prospect and made the most of his opportunity in the majors this season. Their development is crucial given their role in the Beltre decision.

Texas is out of the postseason and Beltre’s contract is up, which makes it an appropriate time to reflect on how this move worked out for the Red Sox. There’s plenty still to be determined, but also enough evidence available to make the picture a little clearer.

Let’s start with Beltre. He slashed .309/.358/.514 from 2011-15 and with a solid 24.2 WARP in that time. He was a three-time All-Star, won a pair of Gold Gloves and Silver Sluggers and in 2012 was third in the AL MVP voting. Simply put, the Rangers, who made the postseason three of those five years, got more than their money’s worth out of Beltre.

As for the Red Sox? They’ve gone through three starting third basemen — Youkilis, Will Middlebrooks and Pablo Sandoval — in the past five years, with a few part-timers sprinkled in, and none of their numbers comes close to what Beltre has accomplished. Boston was 21st in wOBA over that time and is now locked in a regrettable contract at the position thanks to Sandoval. The Sox seemingly have no better answers.

Don’t believe it’s been that bad? Here’s how it’s looked year by year.

2011

Adrian Beltre: 124 games; .304 TAv; .381 wOBA; 4.6 WARP

Kevin Youkilis: 120 games; .287 TAv; .366 wOBA; 2.6 WARP

This one is actually pretty close. Both players had All-Star-caliber seasons with the offensive numbers ending up nearly identical. At this point it looks like not re-signing Beltre was the right decision. The Red Sox made big acquisitions at other spots, got their two picks and hardly had a drop-off at third in Beltre’s absence. So far, so good.

2012

Adrian Beltre: 156 games; .322 TAv; .388 wOBA; 5.7 WARP

Kevin Youkilis: 42 games; .247 TAv; .328 wOBA (2012 total); -0.1 WARP

Will Middlebrooks: 75 games; .279 TAv; .357 wOBA; 1.8 WARP

Youkilis had a brief and forgettable stint with the Bobby Valentine-led Sox before being traded to the White Sox in June. But no need to worry. Boston called up Will Middlebrooks and the rookie had a promising campaign before a wrist injury cut it short. Meanwhile, Beltre was having what would be his best season over the course of the deal. Still, Middlebrooks’ emergence continued to make the Red Sox look smart.

2013

Adrian Beltre: 161 games; .312 TAv; .379 wOBA; 5.7 WARP

Will Middlebrooks: 94 games; .240 TAv; .300 wOBA; 0.8 WARP

This is where the discrepancy starts to show. Beltre continued to produce at an elite level, while Middlebrooks struggled in his second season, battling both injury and poor play. The Sox got a bulk of the season out of Middlebrooks, while Jose Iglesias, Xander Bogaerts, Pedro Ciriaco and Brandon Snyder all saw time at third as well. It was too early to say Middlebrooks wasn’t the long-term solution at third by this point, but it certainly wasn’t looking good.

2014

Adrian Beltre: 148 games; .320 TAv; .380 wOBA; 4.9 WARP

Will Middlebrooks: 63 games; .188 TAv; .238 wOBA; -1.2 WARP

Xander Bogaerts: 44 games at third; .247 TAv; .294 wOBA; 0.7 WARP

Brock Holt: 39 games at third; .261 TAv; .317 wOBA; 1.6 WARP

This one is complicated from a Red Sox perspective, but nothing short of disastrous. Middlebrooks spent more of the season on the disabled list than actually playing. That opened up third base for Xander Bogaerts, who had an ugly 44-game stint at third before going back to shortstop, and Brock Holt. Needless to say no one in Boston could come close to Beltre’s 2014 production, which resulted in another All-Star selection.

2015

Adrian Beltre: 143 games; .278 TAv; .337 wOBA; 3.3 WARP

Pablo Sandoval: 126 games; .229 TAv; .288 wOBA; -1.4 WARP

This was arguably the worst result of letting Beltre walk. In need of a viable third baseman, the Red Sox signed Pablo Sandoval to a five-year, $95 million contract, a deal nearly identical to Beltre’s after 2010. The result has been far, far worse. Sandoval had the worst season of any qualified third baseman in baseball, both from an offensive and defensive standpoint. Beltre’s 2015 was a drop-off from the previous four seasons, but far from a disappointment as he was still one of the most valuable third basemen in the game. Oh yeah, and, barring a miracle, Boston still has four more years of Sandoval.

The Red Sox would’ve been better off with Beltre over any other third baseman they’ve used over the last five years, and it would’ve come at a fair price. That’s evident, but the value of the return is still to be determined.

Boston got two prospects out of Beltre, and both have developed into major leaguers. Bradley is a Gold Glove-caliber outfielder who can’t consistently hit big league pitching. He had a nightmare rookie season at the plate in 2014, and spent most of last season in Triple-A Pawtucket before getting called up permanently in August. He finished 2015 with a .280 TAv in 255 plate appearances and was one of the team’s best hitters over the last six weeks of the season, a sizeable improvement from the year before that gives him a legitimate shot at a starting job next season.

Swihart has the potential to be a star. Injuries to Christian Vazquez and Ryan Hanigan forced the Sox to call him up earlier than expected this season, but he improved steadily as the year went on, establishing himself as a serviceable catcher with a solid bat. (He finished 12th among catchers with at least 300 plate appearances with a .312 wOBA.) His development more than anything else could be the difference between whether or not losing Beltre was worth it.

Swihart’s future with the Red Sox, however, is uncertain with Vazquez expected to be ready for next season. Swihart could be a trade chip, or he could be forced to earn the spot over Vazquez, who was the odds-on favorite to be the team’s starting catcher this year before undergoing season-ending Tommy John surgery in the spring.

In a world where prospects are overrated and each year is unpredictable, it’s often better to go with the safe bet. In hindsight, that’s exactly what Beltre would’ve been. The Red Sox have received little production at third over the last five years, all while Beltre has consistently been one of the game’s best. His presence would’ve made a difference as Boston stumbled to three last-place finishes.

The potential of both Swihart and Bradley is exciting, and they may be around far longer than Beltre would have. But Bradley, at best, is a bottom-of-the-order hitter with a spectacular glove. Swihart may become a star, or he may not. Worst of all, there may still be four more years of Sandoval.

Perhaps the future will swing the decision more in the Red Sox’s favor, but unless both Swihart and Bradley blossom, they would’ve been much better off with Beltre.

Photo by Carey Edmondson/USA Today Sports Images

Shaw hasn’t gone on a better run than all other Red Sox players, as Jackie Bradley casually turned into Barry Bonds for a month. He’s also not the most talented guy on the team, as either Bogaerts or Betts likely takes claim to that title. However, Shaw has certainly come out of nowhere more than any of the other young players, and there’s something special about watching that kind of breakthrough performance.

While watching Shaw has been fun, however, it’s only natural to eventually start thinking about how sustainable this kind of performance is from a rookie. As such, I thought it might be useful to compare Shaw’s first MLB season to other rookies of recent past, and see if it can tell us anything about Shaw’s future. I looked through Baseball-Reference’s play-index to find similar rookie seasons from the past 15 years, and the following names were the most interesting.

Will Middlebrooks

Maybe it’s the eternal pessimist in me, but the first name that came to mind when I first really started thinking about Shaw’s season was Will Middlebrooks. They are both Red Sox corner infield prospects, and they look kind of similar [editor’s note: Will is infinitely more handsome] so I suppose it’s a natural comparison.

On the surface, these players have had similar debuts, but the more you look at it, the bigger advantage Shaw has. Although he has slightly less power than Middlebrooks, he has a much better approach at the plate, suggesting his performance may be a little more sustainable. That doesn’t necessarily mean Shaw’s career won’t follow Middlebrooks’ trajectory, but there’s certainly more to build from now than there was then, albeit in a slightly smaller sample size.

Jeff Francoeur

Alright, maybe I do have a pessimism problem. Francoeur is another guy who jumped out to an amazing start, only to later flame out. Sure, he still has a job in the majors, but he’s fallen a long way since being a rookie phenom on the cover of Sports Illustrated.

These lines are quite similar, with Shaw showing better plate discipline (something that Francoeur has never exactly been known for) while Francoeur showed a more refined hit tool. The good news is the lack of walks is what likely undid the latter. The bad news is that his power also dissipated in a major way as his career worn on. Shaw’s overall line is great, but he’ll need that power to stick around if he’s going to be an everyday player in this league.

Evan Longoria

Now we can safely put aside my pessimistic tendencies, as we have a bonafide superstar on the list of Shaw’s comparables. Both players are corner infielders, which is probably the only two things these players have in common. Shaw took a long time to push through the minors and had relatively little hype. Longoria made the majors shortly after he was drafted and was a highly-touted prospect at the time.

Despite the many differences in these players’ backgrounds, they had very similar experiences in their first taste of the major-league level. In fact, these players have been almost identical, with Longoria showing a bit more power but sacrificing some strikeouts in the process. Of course, it has to be mentioned that Longoria’s performance came over the course of a full-season while Shaw’s has come in just a couple months of work. It’s not a perfect side-by-side, but just going by the numbers, these are very similar first-season experiences.

Kyle Schwarber

This was, to me, the most interesting name on the play-index results. Schwarber was a top-ten pick just a year ago, turned into one of the premier hitting prospects in the game and has already carved himself a role at the major-league level. Simply put, coming into the season, Schwarber was on people’s radars and Shaw was not. How do their 2015 rookie campaigns compare?

Schwarber has certainly been the better rookie this season, but given their respective backgrounds, it’s surprisingly close. On top of that, Schwarber carries the higher strikeout rate, and that’s the one stat that has seemingly led to downfalls from top prospects. That’s not to say Schwarber won’t have the better career than Shaw — the opposite is almost certainly true — but the fact that you can make a case for Shaw’s long-term abilities is noteworthy on its own.

***

So, we have a bunch of comparisons, but is there anything that can really be learned from them? If anything, Shaw’s long-term outlook seems much better after comparing him to other recent rookies. The two players he has most in common with are Evan Longoria and Kyle Schwarber. One is a current superstar and possible future Hall of Famer and the other one is a player many have pegged as a future star. While he does have some in common with Middlebrooks and Francoeur, he boasts much better plate discipline than both of them, which was the biggest contributor to their respective downfalls.

None of this means that Shaw is owed a full-time role in 2016, but it does give much more optimism about what his future holds. For a player who seemingly came out of nowhere to hit the cover off the ball, that’s a big first step.

Photo by Andy Marlin/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

From 1998 through 2011 the Red Sox never won fewer than 82 games, a 14-year stretch that included two World Series championships, 10 second-place finishes in the AL East (damn Yankees) and a near annual late-season playoff push. Then, after a beer-and-chicken-fueled pennant race tailspin in 2011, a collapse which cost the Red Sox a playoff appearance, a sub-70 win (non-strike) season invaded Fenway Park in 2012 for the first time since — wait for it — 1965.

The 2012 Red Sox featured an ugly combination of underperformance (specifically from the pitching staff), injuries, and a Bobby Valentine managerial experiment gone wrong. The starting rotation, which was supposed to be anchored by Jon Lester and Clay Buchholz, didn’t feature a single regular with an ERA+ better than average. The bullpen wasn’t much better, as far too many high-leverage innings went to the likes of Alfredo Aceves and Mark Melancon, a duo that combined for an ERA approaching six and allowed 19 home runs. The offense held its end of the bargain better than the pitching staff, but it was plagued by key injuries to David Ortiz and Jacoby Ellsbury while surrendering too many plate appearances to the Mike Avileses and Pedro Ciriacos of the world.

From 1998 through 2011 the Red Sox never won fewer than 82 games.

Following an all-too-brief, all-too-enjoyable respite from the cellar in 2013 (more on that later), the 2014 Red Sox again finished in last-place as the Orioles ran away with the divisional crown. Young players like Xander Bogaerts and Jackie Bradley Jr. were entrusted with starting roles and didn’t produce as expected (particularly Bradley), while the offense as a whole was uncharacteristically punchless – only David Ortiz (35), Mike Napoli (17), and Bogaerts (12) hit more than 10 home runs. The starting rotation, outside of Jon Lester and a league-averagish John Lackey (both dealt away at the deadline), was a disaster. Bad Clay Buchholz returned, and the back-end of the staff rotated four different pitchers with at least 10 starts and a strikeout-to-walk ratio under two.

The silver lining, of course, is that the 2013 Red Sox won another World Series and this year’s team, by both PECOTA and FanGraphs, projects to finish atop the muddled AL East. One would hope that a trip to the basement doesn’t have to precede every winning season in a post-Theo world, especially for a franchise with Boston’s financial clout, but there are a number of ways in which recent Red Sox failures have helped set up future success.

Major-league development of young players

Teams that win every year have to deal with a delightful burden: they have to play every game to win. For the most part, that’s a good thing. You know, for obvious reasons. On the downside, it makes it difficult to incorporate young players into the major-league mix.

Take the Yankees, who’ve only made one playoff appearance over the last three seasons, and missed October baseball in consecutive years in 2013 and 2014 for the first time since 1993. Despite the postseason whiffs, the Yankees have stayed in the hunt in both of those campaigns, failing to bow out of the race until season’s end. In part because of that, last year’s Yankees team, for example, only had one position player under 30 years old – Yangervis Solarte, who was traded in July for the older Chase Headley – rack up more than 200 plate appearances. In fact, New York hasn’t handed a significant amount of playing time to a position player under age-25 since Eduardo Nunez turned the trick in 2011, perhaps by using a fake date-of-birth that aged him five years.

Here’s a list of 25-and-under position players that received more than 200 plate appearances for the Red Sox in 2014 alone:

In each case, the Red Sox were able to glean valuable information about young talent, giving them a better foundation from which to make decisions heading into 2015.

Middlebrooks, Bradley, and Bogaerts were expected to be major contributors right out of the gate last season, back when the Red Sox thought they were contenders. Between two more trips to the disabled list and an otherwise hackworthy repeat of past struggles when he was on the field, Boston finally decided to pull the plug on the Will Middlebrooks Project, dealing him to the trade-happy Padres this offseason for defense-oriented catcher Ryan Hanigan. Like Middlebrooks, Bradley Jr., despite all-world defense in centerfield, played his way out of the 2015 outfield picture with a cringe-worthy .198 TAv in a lengthy look last season after a lackluster debut in 2013. Bogaerts largely struggled as well, but at just 21 years old, there were enough positive strides to allow the Red Sox to stick with him essentially all season – and with a playoff berth unlikely by mid-summer, there was little reason to ship him off to Pawtucket in hopes of finding a short-term replacement.

Fielding a last-place club in 2014 allowed the Sox to call up prospects later in the year for extended cameos.

Perhaps more beneficial than sticking with young players mired in season-long slumps, fielding a last-place club in 2014 allowed the Sox to call up prospects later in the year for extended cameos. One of those players was minor league sensation Mookie Betts, who was hitting .346/.431/.529 between Double-A and Triple-A (at age-21) when Boston decided to make him its everyday center fielder in mid-August. Betts rewarded the Red Sox by hitting .317 in September while showing the type of plate discipline that helped him climb the prospect ladder with a helium-fueled jetpack. Betts started 2015 as the everyday center fielder and, per PECOTA, is projected to be the best player on the team.

The Red Sox also called up catcher Christian Vazquez on July 9th, a defensive specialist who lived up to his name in 50 starts behind the dish last season. Though Vazquez only OPSed .617 in 201 plate appearances, he displayed enough pitch-framing expertise (plus-32.3 framing runs/7,000) and control of the running game (52 percent caught stealing percentage) to make him the Sox’s Opening Day choice this spring until Tommy John surgery reared its ugly head.

The 2014 pitching staff featured a similar trend: the quintet of Rubby De La Rosa (25), Brandon Workman (25), Felix Doubront (26), Allen Webster (24), and Anthony Ranaudo (24) received 61 combined starts, enough work for Boston to decide that its 2015 rotation, at least initially, wouldn’t include any of them.

Scouting and stat-based projections give a team a solid idea of what a minor league player can provide once he reaches the majors, but there’s no replacement for evaluating that player in action against the game’s best competition. Whether it was Mookie Betts’ .388 on-base percentage or Anthony Ranaudo’s 8.8 strikeout percentage, last year the Red Sox were able to use Fenway Park as a test ground for prospects, a benefit that wouldn’t have been available had they been in the thick of a playoff hunt.

The trades (and non-trades)

In both 2012 and 2014, the Red Sox, not surprisingly, didn’t make a single (major) trade that was aimed at improving the current team’s status.

The Red Sox’s failures in 2014 led to them landing Eduardo Rodriguez.

Last year, Boston made a number of deals that were focused on a quick 2015 turnaround. The Sox dealt Jon Lester and Jonny Gomes to the A’s for Yoenis Cespedes (who ultimately turned into Rick Porcello), ensuring they’d get something for Lester if a long-term free agent deal never materialized. John Lackey was dealt at the deadline (along with lefty Corey Littrell) for Allen Craig and Joe Kelley, two players who figure to make an impact on this year’s team. The Red Sox also made a number of deals that are typical of losing clubs, shipping out spare parts for prospects of various promise: Andrew Miller was sent to Baltimore for left-hander Eduardo Rodriguez (currently ranked fourth in the system), Felix Doubront was traded to the Cubs for a player to be named later (eventually infielder Marco Hernandez), and Jake Peavy was dealt to San Francisco for two pitchers named Edwin Escobar and Heath Hembree.

If we harken back a little further, outside of a few small-scale moves, the 2012 Red Sox largely stood pat — that is, of course, until Ben Cherington and Co. executed a late-August blockbuster that sent Adrian Gonzalez, Carl Crawford, Josh Beckett, Nick Punto, and cash to the Dodgers in exchange for James Loney, Ivan Dejesus, Webster, Rubby De La Rosa, and Jerry Sands. That trade didn’t work out quite as well as planned, only because Webster, the top prospect brought over in the deal, disappointed in 18 starts in the majors before being shipped to Arizona with De La Rosa for Wade Miley this offseason. More than the disappointing return, though, the trade allowed the Red Sox to famously get back to their 2004 roots. They used their newfound financial freedom on short-term, value-oriented deals in the 2012-2013 offseason, adding the likes of Shane Victorino, Gomes, Napoli, and Koji Uehara, all of whom played large roles in Boston’s resurgent 2013 World Series run.

Another benefit to major league suckitude: not having to exchange prospects for short-term needs. Here’s what’s happened to Kevin Goldstein’s 2012 Red Sox top 20:

1. Xander Bogaerts, SS – Still in organization, starting shortstop
2. Brandon Jacobs, OF – Traded to White Sox in 2013
3. Will Middlebrooks, 3B – Traded to Padres this offseason
4. Ryan Lavarnway, C/DH – Claimed off waivers by Dodgers this offseason
5. Blake Swihart, C – Still in org., No. 1 ranked prospect
6. Bryce Brentz, OF –Still in org.
7. Matt Barnes, RHP – Still in org., No. 7 ranked prospect
8. Garin Cecchini, 3B – Still in org., No. 8 ranked prospect
9. Anthony Ranaudo, RHP – Traded to Rangers in 2015
10. Jose Iglesias, SS – Traded to Tigers in 2013
11. Sean Coyle, 2B – Still in org.
12. Jose Vinicio, SS – Still in org.
13. Jackie Bradley Jr., OF – Still in org.
14. Henry Owens, LHP – Still in org., No. 2 ranked prospect
15. Alex Wilson, RHP – Traded to Tigers this offseason
16. Brandon Workman, RHP – Still in org.
17. Drake Britton, LHP – Claimed off waivers by Cubs this offseason
18. Stolmy Pimental, RHP – Traded to Pirates in 2012
19. Williams Jerez, OF – Still in org.
20. Cody Kukuk, LHP – Still in org.

The Red Sox have held on to 13 of the 20 prospects from a list made over three years ago. Sure, Boston swapped Jacobs for relief help during the 2013 season, but he was already on the downtrend and certainly hasn’t panned out. Most of the other players traded or released on this list – like Middlebrooks and Lavarnway — were sent packing only after Boston had seen enough to know they were no longer part of the long-term plan. In turn, the Sox have been able to stash players like Bogaerts, Swihart, Owens, Barnes, Ceccini, and Bradley Jr. away in the minors, patiently waiting as they develop into major-league contributors or premium trade bait. Range closer, to Baseball Prospectus’ 2014 Red Sox top 10, and you’ll find only one player – Webster – who has been dealt from that list.

Thanks to two losing seasons in three years and a good dose of patience, the Red Sox have been able to hoard a collection of young talent that rivals any team outside of Chicago.

Increased amateur budgets

Perhaps the most tangible area positively impacted by poor major-league records is amateur spending, an area where winning teams are punished by the rules accompanying the latest CBA. In both the stateside amateur draft and in the international amateur free agent market, teams are given an allotted signing bonus pool based on their previous year’s record and they’re encouraged to stay within those guidelines with a set of increasingly harsh penalties for over-spending. Below is a table that shows the Red Sox bonus pools for the draft and international amateur market in both 2013 and 2015 (data from Baseball America), the years after they finished last in the AL East:

*Estimated, as official figures haven’t been released

Let’s start with the draft. The numbers here aren’t staggering at first glance, but consider this: when the Sox scored the seventh overall pick in the 2013 draft, it was their highest first-round selection since they took Trot Nixon at No. 7 in 1993. In fact, Boston had a recent stretch from 2004 through 2010 where it didn’t have a single pick inside the first-round’s top 20. Yes, the burdens of success — of course, the Red Sox did an excellent job developing home-grown talent in many of those years, a credit to their ability to draft and develop. Still, early draft picks are a good thing, especially when you forget about how you got them.

The Red Sox picked Trey Ball seventh overall in 2013. They have the seventh overall pick again in 2015.

In 2013, the Red Sox signed both of their first two picks, left-handed pitcher Trey Ball and right-handed pitcher Teddy Stankiewicz, to below-slot deals. That, combined with a run of $10,000 college senior signings in rounds eight through 10, allowed the Red Sox plenty of flexibility at other points in the draft. The Sox were able to lure highly coveted catcher Jon Denney away from an Arkansas commit with an above-slot third-round deal, and they were also able sign four players from rounds 11 through 40 to deals over $100,000, including a $440,000 splurge in the 30th-round on high school outfielder Nick Longhi. The results have been mixed – Ball’s dipped out of most Red Sox top 10s while Denney didn’t play at all in 2014 after a spring training arrest, but both Stankiewicz and Longhi made solid pro debuts. Regardless of the returns on a draft just two years old, thanks to their 69-win season in 2012, the Red Sox were able to take high-upside talent early in the draft while using their hefty signing bonus pool for later round flexibility.

The Red Sox are again set to draft seventh in the 2015 draft, another positive side effect from last year’s 71-win campaign. And since the first 10 picks in the draft are protected, the Red Sox were able to sign both Pablo Sandoval and Hanley Ramirez while retaining their top overall selection. The Sox did have to surrender their next two picks as part of their offseason spending spree, leaving them without a second pick until the third-round (81st overall) and with a middle-of-the-pack $6.5 million signing bonus pool. The seventh overall pick gives Boston another chance to add premium talent early, even if injuries and a lack of star-power are taking their toll on the top of this year’s crop. There’s a possibility Boston takes a stab at working out a below-slot deal with a recent Tommy John casualty like Brady Aiken (last year’s first overall pick) or Duke’s Mike Matuella, again using saved first-round money to attract hard-to-sign talent later on.

On the international amateur market, Boston also reaped the rewards of a $3 million-plus bonus pool during the 2013-2014 July 2 signing period. They nabbed third basemen Rafael Devers for $1.5 million, and he used a mature left-handed stroke to post a .910 OPS as a 17-year-old in two rookie league stops last season, soaring up Red Sox prospect lists and sneaking inside Baseball Prospectus’ top 101 in the process. Boston used every penny of its budget during the 2013-2014 signing period, which included three more six-figure signees: left-handed pitchers Emmanuel DeJesus ($787,500) and Jhonathan Diaz ($600,000), and outfielder Yoan Aybar ($450,000). In fact, the Red Sox actually spent nearly five percent over their bonus pool, a maneuver that cost them a 75 percent tax on the overage but no future spending restrictions.

Early draft picks are a good thing, especially when you forget about how you got them.

During the upcoming 2015-2016 July 2 signing period, the Red Sox again have one of the highest bonus pools in the league; this year, however, they probably won’t be able to spend all of it. Since they blew past their budget in the most recent J-2 signing period with a class led by Cuban sensation Yoan Moncada, Boston won’t be able to ink an international amateur for more than $300,000 for the next two signing periods. All isn’t lost, as the Red Sox can still spend as much of their pool as possible stockpiling $300,000-and-under international lottery tickets while trading away what’s left of the pool money.

Spending restrictions have made it harder for big-market teams to flex their financial muscle in amateur markets (well, sort of), but the Red Sox have been able to infuse their organization with high-upside talent thanks in part to their on-field collapses in 2012 and 2014, an unforeseen circumstance that’s helped them construct a top-heavy and deep minor league pipeline.

***

It’s dangerous to give the Red Sox too much credit — after all, in Cherington’s three years as general manager, the Sox have amassed an uninspiring .488 winning percentage with a yearly payroll that’s rivaled by only two or three teams. Where Cherington and Co. deserve praise is for their willingness to take their last-place medicine in stride, instead of throwing all their chips on the table in an all-out effort to win 80-odd games every season. For their patience, the Red Sox have been rewarded with a major-league roster full of young stars and capable veterans, a healthy farm system stocked with equals parts big-league ready talent and long-term projects, and the payroll flexibility to remain a threat for any free agent or contract extension candidate (see: Porcello, Rick).

There’s a point where it all could have gone wrong, where the Red Sox could have panicked and sold off the future for post-prime short-term upgrades. There’s a point where the Red Sox could have turned into the Phillies, grasping to the winning days of yore with the wrong players. Instead, as the new-look roster played home run derby on Opening Day against a Phillies team desperately fighting off the last stages of a full-on rebuild, the Red Sox have quickly repositioned themselves as an American League power. Losing 90-plus games in two of the last three years wasn’t in Ben Cherington’s blueprint for long-term success, but the way he handled the Red Sox recent misfortunes might deserve a new chapter of its own.

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