There's been some interesting discussion of the Brewers' situation in the comments today, and with the Pirates hopefully entering a boom period similar to (or maybe better than) the Brewers' good run from 2007 through 2012, it's worth looking at what's going on in Milwaukee now that their boom period might well be over.
First, a basic outline:
The Brewers had 12 straight losing seasons from 1993 through 2004. In 2005, they finished 81-81, and then in 2007, they finally won more than they lost, going 83-79. In 2008, they won 90 games and went to the playoffs, thanks to a homegrown core of Ryan Braun (4.6 WAR), J.J. Hardy (4.4 WAR), Ben Sheets (4.3 WAR), Rickie Weeks (2.3 WAR) and Prince Fielder (1.4 WAR). A strong season from veteran Mike Cameron also helped. In July, the Brewers acquired C.C. Sabathia for what turned out to be Michael Brantley and three busts, and Sabathia made 17 spectacular starts before leaving via free agency.
In 2009 and 2010 the Brewers had two more losing seasons. After 2009, they sent Hardy to the Twins for Carlos Gomez. Following the 2010 season, they traded Brett Lawrie to the Blue Jays for Shaun Marcum and Lorenzo Cain, Alcides Escobar, Jake Odorizzi and Jeremy Jeffress to the Royals for Zack Greinke. They won 96 games and went back to the playoffs, losing in the NLCS. After that, they lost Fielder to free agency and sent Greinke to the Angels for Jean Segura and two other players.
In 2013, of course, the Brewers went 74-88. This year, they're probably looking at something like a .500 season, and they've got the worst farm system in baseball. I expected to find a lesson in here about the perils of going "all-in," but the Brewers' case is more complex than that. Some of their big trades in the last few years (Hardy for Gomez, for example, and Greinke for Segura) have been deft, and some of the ones that appeared to be very risky at the time, like the Sabathia deal, haven't really come back to bite them. I went to Miller Park in 2009, after Sabathia had already signed with the Yankees, and the Brewers still had a Sabathia banner hanging there. The Sabathia deal doesn't seem like one they regret, and I don't think they should. As a result of their main going-for-it trades, they lost some good players in Brantley, Lawrie, Cain, Escobar and Odorizzi, but they got Segura and Marcum and some excellent, important pitching from Sabathia and Greinke. If they could do that again, I bet they would.
The real problem is that their farm system hasn't produced. Their 2006 draft was a complete whiff. 2007 produced Matt LaPorta, who looked like the key piece in the Sabathia deal at the time, and Jonathan Lucroy. In 2008 they got Lawrie and Odorizzi. In 2009, they got Khris Davis, Scooter Gennett and Mike Fiers. That's not nothing, but it's not the star power an organization like the Brewers needs. Their last few drafts don't look like anything to write home about, either. The failures of their two 2011 first-rounders, Taylor Jungmann and Jed Bradley, are the single biggest cause of their poor current farm system.
Poor, or unlucky, scouting and development have something to do with why their farm system is so bad. But they also didn't participate in the Pirates/Royals overslot bonanza in the 2008 through 2011 drafts, and they haven't gotten much recently out of Latin America -- Escobar and Wily Peralta are the only meaningful Latin prospects they've developed recently, and they signed both those guys about a decade ago. And their farm system has struggled, in part, because of their success in the majors. The Brewers haven't picked in the top ten since 2007, and the Pirates have signed five top-ten picks since then, including three top-two picks.
I liked the Brewers' signing of Matt Garza, and I can't fault them for trying to be competitive this year, since they still have a good core of position players. Given their payroll limitations and their farm system, though, they might want to consider rebuilding if they don't play well the first few months of the season. Their successful, or semi-successful, 2007-2012 run was fueled by top draft picks like Braun, Fielder and Weeks, and the fact that they don't have high draft picks anymore is the single biggest difference between what they were then and what they are now.
If there's any takeaway here that the Pirates can do something about, it's that getting good talent in Latin America is important. The Brewers might have had an easier time compensating for not having top draft choices if they had been producing Latin American talent. Scouting and developing well are also crucial, of course. But beyond that, it's much easier to build a championship-caliber organization if you have top draft picks. The Pirates are beginning to reap the benefit of being so bad for so long, with early-first-rounders Andrew McCutchen, Pedro Alvarez, Jameson Taillon and Gerrit Cole all making an impact or on the verge of doing so. But starting this year, they won't be able to depend on top draft picks for awhile, and they'll be faced with the tough task of avoiding the mess in which the Brewers organization now finds itself.