Dave Dombrowski was hired by the Boston Red Sox on Tuesday, August 18th of 2015, thirteen days after being fired by the Detroit Tigers. The General Manager in Boston at the time, Ben Cherington, a former Theo Epstein lieutenant and disciple, resigned later that night.

Even while en route to their third last place finish in four years, there was substantial trepidation amongst Red Sox fans about the hire. Not surprisingly for someone who’s been in the game since 1978, Dombrowski’s reputation preceded him. “Dealin’ Dave” was known for having no reservations about moving the kind of minor league talent that the Epstein and Cherington regimes fiercely protected.

The immediate question in the wake of Dombrowski’s appointment was what it meant: would the Red Sox remain committed to player development and home grown talent, or would the system be strip-mined and sold off for veterans? The retention of Mike Hazen as Dombrowski’s GM seemed at the time like an olive branch, a sign that the front office tradition that won Boston three world championships in a decade – one of which came at the expense of Dombrowski’s Tigers – would be respected.

Fifteen months later, Hazen is gone, and with him the last vestiges of the front office Theo Epstein created. As Peter Gammons says, “The organization is far different than the one [Theo] created; more than a dozen, many of them key people, have left the organization since Dave Dombrowski took over.” An organization that once prided itself on its ability to draft and develop talent was no more, as was originally feared.

All of which explains how it’s possible to be crushed that the Boston Red Sox acquired a player the caliber of Chris Sale. The following is a look at the Good, the Bad and the Ugly.

The Good

• The Deal is Defensible:
  As many writers have noted, the deal is not without its merits. Absent context, even so-called “prospect hoarders” would be forced to admit that it can be defended. Most obviously, the deal was completed without affecting the major league roster. Once, Sale would have been traded for nothing less than a Betts, Bogaerts, or at worst, Bradley. Instead, all three remain with the club. It’s also fair to note that even the best prospects in the deal – Kopech (who’s comped to Syndergaard) and Moncada (who’s comped to Cano) – do not come without question marks. Basabe and Diaz, for their part, are even further away and thus riskier. Evaluating the deal on its own merits, you might not take a single player – even one as good as Sale – for multiple high upside prospects (one of whom is regarded as the best prospect in baseball) because you’re concentrating your risk. But you might, because:
• Sale is Good:
  Excellent, in fact. By fWAR, he was the seventh best pitcher in the league last year, ahead of names like Kluber, Bumgarner, Tanaka, Price, Hendricks and Lester. If you go back to 2012, in fact, his first season as a starter, there are three pitchers who’ve been more valuable: Kershaw, Scherzer and (by a tick) Price. By virtually any metric, Sale is one of the best pitchers in baseball. And he’s not the only star.
• The Roster is Good:
  Sale isn’t the only good Red Sox starting pitcher, as you might have heard. The reigning American League Cy Young winner, in fact, could be the number three starter for the club – and the final two spots are likely to be filled by pitchers who either have been an All Star (Buchholz, Pomeranz, Wright) or have that kind of ability (Rodriguez). And while the offense has an enormous hole to fill with the departure of Ortiz and is unlikely to lead the league in runs again – let alone by a hundred – it is capable and with the exception of third base and arguably DH has no obvious holes. Nor is this a typical Dombrowski club with incredible starting pitching but a porous bullpen: if Carson Smith makes it back by midseason, the Red Sox could throw five guys late in the game who hit the high 90’s in Barnes, Kelly, Kimbrel, Smith and Thornburg. Even the depth is reasonable, with three potential catchers, Brock Holt and Marco Hernandez and players like Sam Travis waiting in the wings at Pawtucket. And not only is the lineup good.
• The Core Players Are Young:
  In Betts, Bogaerts and Bradley, the Red Sox have an enviable trio of talented and young players. Bradley’s the elder statesman at 26, while Betts and Bogaerts are 24. As is Blake Swihart. Andrew Benintendi, meanwhile, who presumably will start in left field, is 22. That is the kind of core that every team in baseball that’s not the Cubs would envy and take in a second. And even after all the trades, the farm system isn’t quite tapped out.
• Not All the Remaining Prospects Are Bad:
  While the Red Sox minor league system is in the worst shape it’s been in in over a decade, and has effectively no depth, there are two players left over with potentially high ceilings in Jason Groome and Rafael Devers. Neither are exactly knocking on the door to the major league club, but they remain a top two that are at least the equal of most other systems in the game.

The Bad

• Tick, Tick, Tick:
  One of the things that everyone seems to agree on is that the price for Sale came down. From “a Betts/Bogaerts/Bradley to start the conversation,” the White Sox ended up settling for a package that included no players from the major league roster. The question no one seems to be asking is: why did the price come down? One potential, frightening answer: injury risk.Gammons: “A source close to Jerry Reinsdorf, the most loyal of owners, says he is concerned about Sale’s long-term shoulder wear given his delivery and the extreme effort.”

  Olney: “According to sources, the White Sox are pushed by a concern in some corners of the Chicago organization that it’s inevitable the All-Star left-hander with the contortionist pitching mechanics will eventually break down.”

  Presumably the White Sox know more about him than anyone else, and they lowered the price to acquire him. And then there are the numbers.

• Warning Signs?:
  Sales’ FIP in 2016 was 3.46, the worst of his career. The last time he had a FIP above 3, in fact, was 2013. He also struck out batters at the lowest rate since his debut in 2012. The rumor early in the season was that he was trying to pitch more to contact, but as Keith Law notes he lost a mile and a half of velocity. There’s nothing in his numbers that screams red flag, but neither is the trajectory and more importantly, the dip in velocity, encouraging.
• The Odds:
  To read some of the initial reactions to the trade, you’d think that trading for Sale guaranteed a World Series berth, if not title. But the math of the postseason is remorseless. Even a club as talented as last year’s Cubs, who were arguably the best defensive team in history and fronted by a similar trio of Cy Young types had something close to a 25% chance of winning the World Series. They won, of course, much to the delight of Cubs fans everywhere, but they were also down three to one to an Indians team short two of its best starters and if not for the rain delay in Game 7, who knows how that series turns out. None of which is to say that you don’t go for it when you can, but given the long odds of even the best teams reaching the series let alone winning it, it’s important to always keep the long view in mind. As Dombrowski should know well from his time in Detroit: it’s not that often that a team opens a series almost no hitting the opposing club the first three games and loses.

• The Context:
  Even for the Red Sox fans most devoted to prospects, if the Chris Sale trade was Dombrowski’s first trip to the well, he’d be universally hailed.Unfortunately, in fifteen months Dombrowksi has traded seventeen prospects. The following is Sox Prospect’s Top 20 on July 1, 2015, a month and a half before Dombrowski took the reigns.

  1 Eduardo Rodriguez
  2 Yoan Moncada (TRADED)
  3 Rafael Devers
  4 Manuel Margot (TRADED)
  5 Brian Johnson
  6 Henry Owens
  7 Andrew Benintendi
  8 Michael Kopech (TRADED)
  9 Javier Guerra (TRADED)
  10 Deven Marrero
  11 Anderson Espinoza (TRADED)
  12 Trey Ball
  13 Michael Chavis
  14 Pat Light (TRADED)
  15 Sam Travis
  16 Travis Shaw (TRADED)
  17 Ty Buttrey
  18 Mauricio Dubon (TRADED)
  19 Teddy Stankiewicz
  20 Wendell Rijo (TRADED)

  As you can see, he has traded almost half the high end prospect inventory he inherited, and with obvious exceptions such as Devers, many of those that are left likely haven’t been traded because their value cratered (Johnson, Owens, Marrero, etc) or was always minimal (Ball).

  Many will protest, saying that fans become too attached to prospects that haven’t proven anything yet, and that Sale is an elite pitcher. My response to that is that so was Cole Hamels when the Phillies asked for a minor leaguer called Mookie Betts in return for the lefthander’s services. Personally, I’m glad we kept Mookie.

  The net is that Dombrowski has taken a scythe to one of the most fertile farm systems in the game, and in less than two years has left behind a wasteland. Which is a problem because:

• Contracts Are Coming Up Sooner Than You Think:
  Most of the trade reactions you’ll read are focused on the 2017 season, which is understandable because the prospects seem bright, even if the winner of the offseason has historically faired poorly. Thanks to Dombrowski, the outlook in the short term is excellent. But what if we look further out? What does the Red Sox roster look like? The answer, if you’re a Red Sox fan at least, is troubling.Two seasons from now, Price can opt out, Hanley’s status depends on games played and Kimbrel and Pomeranz are free agents.

  The year after that, Bogaerts, Bradley, Porcello, Sale and Thornburg are on the market.

  The year following? Betts, Rodriguez and Smith.

  In four years, then, we could lose four top starters, our closer and setup men, two of three outfielders, and our starting shortstop. This is less alarming if either a) the competitive balance threshold went way up so you could spend with impunity, or b) you have a wave of young players coming up behind them, because you can either swap the departing players for younger replacements, or retain the ones you want and fill in the gaps with young, low cost alternatives. Well, the CBT isn’t going way up, and Boston doesn’t have that wave of young players anymore. Our two best starting pitching prospects in years – Kopech and Espinoza -are gone. One potential superstar position player in Moncada has departed, as have a host of potential starters or utility men in Asuaje, Basabe, Dubon, Guerra and Margot. Even if next year’s draft is incredible – and with all of the front office departures it’s worth asking whether it will be – the impact won’t be felt for years. The well is dry, and the club will have to pay that price eventually.

The Ugly

• Restocking the System:
  As the hemorrhaging from the minor league system continued, the front office has responded by expressing confidence in its ability to restock the farm. This is a confidence which, at best, seems misplaced – and not just because Dombrowski clubs have rarely drafted with any notable success.For many years, there were opportunities for wealthy clubs like the Red Sox to leverage their financial resources to maximum effect in the draft or international markets. These opportunities have since been eliminated.

  First, MLB closed the loophole with the draft, by imposing restrictions on spending so that clubs like the Red Sox couldn’t scoop up elite talent in later rounds simply by being willing to field angry calls from the commissioner’s office. And as of the latest Collective Bargaining Agreement, the last remaining asymmetric opportunity for amateur spending was removed when MLB established a hard cap on international signings.

  In other words, where the Red Sox could once simply outspend other major league clubs on the amateur markets, the reality is today that if anything, high payroll teams are disadvantaged relative to their small market competitors.

  Gone are the days when the Red Sox could acquire a talent like Moncada simply by being willing to spend what the market bore: $60M+, in his case. In short, it’s hard to think of a worse time for the Red Sox to have completely depleted their minor league system.

• The Brain Drain:
  Longer term, the most damage from the Dombrowski era may come from the loss of executive talent. As mentioned above, the Red Sox have already lost a number of key executives – executives who in many cases played critical roles in one or more world championships – in the Dombrowski era. And given the reports that Dombrowski’s inner circle is considerably smaller than his predecessors’, it stands to reason that the Red Sox – in spite of being the Red Sox – may not be able to attract or retain the front office talent that they once did. Which is a significant problem, one that compounds the devastation of our minor league system. As we’ve seen in recent years, so much of the game is now being driven by creativity, from talent identification and acquisition to defensive positioning, but the Red Sox do not appear to be the premier destination they once were.

The Net

During his tenure in Detroit, Dombrowski worked for an owner in his seventies who was desperate to win a world series, desperate enough to mortgage the future in an effort to win in the present. Despite assembling powerful lineups and rotations full of hard throwing Cy Young candidates, the current Red Sox president was never able to give his owner that title. His successor Al Avila, meanwhile, will be the one that pays for Dombrowski’s decisions, and is currently attempting to sell anything that’s not nailed down.

As the ownership group that empowered Theo Epstein all those years ago to build the player development machine Dombrowski has now, finally, dismantled, it’s ironic that John Henry and Co’s willingness to pound the nail in that coffin might have come from watching two men they ran out of town face off in the world series, cementing their Hall of Fame credentials in the process. It took a while, but the best Manager and General Manager the Red Sox ever had may yet have the last laugh.

In the meantime, enjoy 2017.