17 going on 18

After setting a record for most consecutive losing seasons, what’s next for the Pittsburgh Pirates?

Earlier this month major league baseball’s Pittsburgh Pirates clinched their seventeenth consecutive losing season, the longest such streak in the history of North America’s four major sports leagues. As a writer who has covered the Pirates for five-plus years—and watched the team my whole life—it isn’t easy to describe how it felt to watch the Bucs eclipse the record (set by the Philadelphia Phillies, 1933-1948).

People always ask my twin brothers what it’s like to have a twin. They don’t know what to say, because they’ve never been without one. It’s like that with me and the Pirates. I’ll be 30 next month. The last time Pittsburgh won a World Series was the week I was born. The last time the Pirates had a winning season, I was 12. George Bush was president—the first one.

The truth is that it’s tough to be a small-market baseball team, as Joe Posnanski recently pointed out. The Cincinnati Reds recently clinched their ninth straight losing season. The Tampa Bay Rays and Milwaukee Brewers both ended streaks of ten or more consecutive losing seasons in the past decade. (So did the Detroit Tigers, though the Tigers don’t qualify as a small-market team.) And the Kansas City Royals have lost more games in the past 17 years than the Pirates.

Even the low payroll teams that claw their way into baseball’s elite—the Brewers, Rays and Oakland Athletics, for example—have trouble staying there. Meanwhile, wealthy clubs like the New York Yankees and Boston Red Sox are among baseball’s best nearly every season.

Ultimately, though, focusing on baseball’s Gilded Age economic system lets the Pirates off the hook too easily. Given the choices the organization has made in recent years, it’s almost impossible to envision how the Bucs might have succeeded. The Pirates play in PNC Park, arguably the most beautiful stadium in the major leagues, yet Pittsburgh has played the most consistently ugly brand of baseball of any team over the past 17 years.

The Pirates’ losing has its roots in the 1992-93 offseason when the team decided to sign outfielder Andy Van Slyke to a long-term contract (instead of future all-time home run leader Barry Bonds). The Bucs then puttered along for a few years until they somehow wound up contending in 1997. Pittsburgh’s 1997 team wasn’t very good (it won fewer games than it lost), but thanks to the Houston Astros (barely a winning team themselves) that ragtag bunch was still playing meaningful games into the last week of the regular season before the Astros finally clinched. 

Unfortunately, the Bucs learned all the wrong lessons from that brief flirtation with contention. Most years it takes at least 88 or 90 wins to have a realistic chance at a playoff berth; the ’97 Pirates won just 79 games. Considering the four other teams in their division and their lack of a solid talent base, they should have counted their blessings, kept their heads down and built for the future.

Instead, they haphazardly pursued stopgap players and overpaid for mediocre veterans like Pat Meares, Mike Benjamin, Wil Cordero, and Derek Bell (who became the most mocked character in the Pirates’ ongoing tragedy by declaring that he would go into “Operation Shutdown” if forced to compete for a starting job in spring training. Never mind that Bell batted a mere .173 the previous year.)

To the amusement of many, the Pirates’ manager at the time, Lloyd McClendon, declared that the signings of Bell and journeyman pitcher Terry Mulholland would “send shockwaves through the industry,” as if rival clubs were shaking in their shoes at the prospect of facing a marginal outfielder and a 38-year-old reliever.

Meanwhile, the Pirates also managed to retard the development of promising youngsters Aramis Ramirez and Jose Guillen by keeping them in the majors even though they weren’t ready. For good measure, the Bucs went on to trade Guillen for almost nothing, handed their own mediocre first baseman Kevin Young a $24 million contract, and spent first-round draft picks on busts like J.J. Davis, Clint Johnston, Bobby Bradley and John Van Benschoten.

For all that, though, the general manager at the time, Cam Bonifay, really did try. For a low payroll team, penning sonnets to every aging free agent who bats an eye is nothing but a waste of ink. But at least Bonifay took seriously the business of building through the minor leagues. Despite all the first-round flops, scouting director Mickey White found solid players in the later rounds of the draft—Nate McLouth, Zach Duke, Ian Snell, Ryan Doumit, Chris Young (the pitcher), Stephen Drew and Jeremy Guthrie. If left to his own devices, Bonifay might have led the Pirates to a winning season or two.

This isn’t to say Bonifay didn’t deserve what he got when the Pirates fired him in 2001. Yet the Bucs, already in the midst of an eight-year losing streak, made things worse with their next GM hire. Bonifay’s replacement was not only incompetent, he was downright malicious. Dave Littlefield, who was hired after the 2001 draft, scuttled contract negotiations with Drew and Guthrie (now solid contributors for the Arizona Diamondbacks and Baltimore Orioles, respectively), beginning a dystopian reign that ranks among the worst in professional sports history.

Littlefield went on to trade Young (who became a valuable starter for the San Diego Padres) for Matt Herges (who was released before ever playing a game for the Pirates). He also cut Bronson Arroyo, who became a key member of the World Series-winning 2004 Boston Red Sox. And employees of other teams openly laughed when Littlefield needlessly allowed five Pittsburgh players to be among the first six picked in the 2003 Rule 5 draft, a draft designed to help talent-poor teams like the Pirates.

At one point, Littlefield was offered future National League MVP Ryan Howard for underachieving pitcher Kris Benson, but he rejected the deal. Pittsburgh’s ownership also aided Littlefield in his quest to destroy the team by ordering him to trade Ramirez—then 25 and a future MVP candidate—for financial reasons.

Of course, the June amateur draft, where the most talented U.S. players are initially acquired, should be the bread-and-butter of any small-market team, but Littlefield showed little interest. He selected Ball State University pitcher Bryan Bullington with the first overall pick in 2002, then announced his hope that Bullington would someday become a #3 starter—you know, an average starter, not the potential ace you’re supposed to get with the top pick. (As it turns out, Littlefield was too optimistic; Bullington has pitched all of 39 major league innings.)

Littlefield’s top picks from 2003 to 2006 (Paul Maholm, Neil Walker, Andrew McCutchen and Brad Lincoln) can best be described as a mixed bag, but in 2007, he left behind a real stinker, choosing Clemson pitcher and future minor league retread Danny Moskos over Georgia Tech catcher Matt Wieters—a superstar in the making. Just as importantly, Littlefield and his scouts ignored the later rounds of drafts and signed no one of consequence from Latin America, leaving gaping holes in Pittsburgh's minor league system, the kind one rarely sees in organizations with big-league teams as talentless as the Pirates.

Yet Littlefield is best remembered for his utterly uninspired lineups. Like Bonifay, he embraced mediocre, aging veterans. Unlike Bonifay, Littlefield’s behavior wasn’t guided by any sense of urgency; he didn’t have a contending season to try to top. He signed veterans just because.

During Littlefield’s tenure, the Pirates could have gone with young, inexpensive power hitter Craig Wilson at either first base or right field, but instead went with veterans like Jeromy Burnitz, Raul Mondesi and Randall Simon (of Sausagegate fame). And in 2006, Littlefield consigned Freddy Sanchez to the bench in favor of $4 million veteran Joe Randa. (Sanchez ended up winning the National League batting title that year after Randa got hurt.) Littlefield even went so far as to trade for washed-up starting pitcher Matt Morris (thereby taking on the $14 million remaining on his contract) in the midst of a 68-94 season.

At this point I wish I could relate a moral to the story, a heartwarming ending, or even a just jarring plot twist. But Littlefield wasn’t a good-hearted fighter with a tragic flaw, or a charismatic villain with a twinkle in his eye. He was a blank-faced dullard who would have pulled any stunt if it meant keeping his job an extra day. And he did keep his job until a combination of poor results and fan outrage over the Matt Wieters and Matt Morris decisions led to his dismissal late in the 2007 season.

So I'm sad to say that there are no heroes here, just a self-centered executive bent on destroying his team, and the people brought in to clean up the mess. Those people are team president Frank Coonelly (who took over for Kevin McClatchy, Littlefield’s old boss and an inept executive in his own right) and general manager Neal Huntington.

Coonelly and Huntington’s task is a difficult one. Fixing a broken baseball franchise isn’t the same as turning around an NFL team, which sometimes requires little more than a handful of shrewd personnel moves. And the organization Coonelly and Huntington inherited is even more badly broken than its long losing streak suggests.

Most lower-echelon major league teams utilize the draft to accumulate top prospects and attempt to rebuild through their farm system. One reason Tampa Bay GM Andrew Friedman was able to lead the Rays from the cellar to the World Series in less than three years was because Tampa’s otherwise incompetent former stewards at least had the sense to collect quality prospects.

But Coonelly and Huntington have had the misfortune of starting from rock bottom. It’s too early to say their first two years have been inspiring, but they appear to be on the right track. Pittsburgh has become one of the most aggressive teams in the draft, and they’ve reestablished the Pirates as suitors for talented Latin American youngsters by building a $5 million facility in the Dominican Republic. And this season they traded the core of their big-league club for young players with varying degrees of ability.

Unfortunately, now is a bad time to be looking to trade for youth. Historically, contending teams undervalue prospects, but today virtually every team is hoarding minor leaguers that have big league potential. And the old adage “You get what you pay for” seems apropos. Most of the players Huntington traded this year can be considered average major leaguers, so the youngsters he acquired in return aren’t among baseball’s best prospects.

Of course, there’s no guarantee that Coonelly and Huntington’s rebuilding plan will work. But for a club in the Pirates’ position, it’s the only plan that can possibly succeed. And while the turnaround figures to take a while, if the Bucs are lucky they’ll be spared the indignity of a 20th consecutive losing season, or a 21st, or 22nd. But for the next year or two—at least—the Pirates are likely to continue their spectacular run of bad baseball.

Charlie Wilmoth is a musician and writer who lives in San Diego and covers the Pirates at SB Nation's Bucs Dugout.