Regrets, I've had a few: A tour of the Pirates' 20-year drought

By Dayn Perry | Baseball Writer

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In a sense, it all started with this ...

When Sid Bream's plodding foot slipped under the tag of Mike LaValliere, the Pirates' 1992 season ended and a two-decade run of misery began. That December, Barry Bonds would sign a lucrative free-agent contract with the Giants, and ace Doug Drabek would ink with Houston. Bobby Bonilla was already with the Mets, and Andy Van Slyke was about to enter a steep period of decline.

What followed was, of course, the longest stretch of consecutive losing seasons in MLB history -- 20 of them, in fact. Over that grim span, the Pirates would be a cumulative 422 games below the .500 mark, and they'd be outscored by their opponents by almost 2,000 runs. They'd finish in last place seven times (in what was then a six-team division, mind you) and churn through seven different managers, four GMs, three ownership groups and two ballparks.

All of those serialized miseries are, of course, over, as the 2013 Pirates have clinched a winning season and also have legitimate designs on the World Series. But before we devote ourselves fully to the nova-bright Pirate present, let's properly eulogize the dismal recent past.

Here, then, is your walking tour of the 1993-2012 Pirates. Come with us, won't you?

And so it begins ...

This streak, like all streaks, started unbeknownst to anyone, least of all the Pirates. On Sept. 22, 1993 -- before 10,031 onlookers at Three Rivers Stadium -- the Pirates fell 6-5 to the Mets in 10 innings and in doing so suffered their 82nd loss of the season, which, of course, made it a losing season. Whom should we blame for this particular defeat, which would cascade into numberless other losses? Well, Mr. Van Slyke went 0-for-5, and Joel Johnston took the loss by giving up a pair of runs in the 10th. And thus it began ...

The history-making loss

Let us leap forward almost 16 years to Sept. 7, 2009. On that day, the Pirates dropped their 10th in their last 11 contests, this one a 4-2 loss to the Cubs. It was that loss that secured the Pirates' 17th straight losing season, and it was that 17th straight losing season that broke the record previously held by the 1933-48 Phillies. It was not only, as noted, the longest stretch of losing seasons in MLB history but also in the entire annals of North American team sports.

The worst of the worst

Of the 20 teams in question, one particular model lowered itself below all others. That was the 2010 team under John Russell. Their winning percentage of .352 is the fifth-lowest in Pirates history (three "Alleghenys" teams from the 19th century also fared worse on a rate basis), and their 105 losses lags only the 1952 Pirates (112) and 1890 Alleghenys (113).

The 2010 Buccos were out-scored by the opposition by 279 runs, and on Sept. 16 they found themselves 50 games below .500 and 34 1/2 games out of first place. They went 17-64 on the road and 2-13 in interleague play. They gave up 20 runs in a game on one occasion and were shut out on 15 occasions. Starting pitchers Jeff Karstens, Ross Ohlendorf and Charlie Morton combined to go 6-33.

One of the lone bright spots was a 23-year-old "sophomore" named Andrew McCutchen, who rather quietly paced the team in doubles, stolen bases and OPS. He would get even better, as it turned out.

The best of the worst

Let's give it to the 1999 team, which was helmed by Jason Kendall, Brian Giles, Kevin Young and a solid rotation. They finished with a record of 78-83 (we'll assume one makeup game was not deemed necessary) and a run differential of -7, which is the best such mark of the drought period. While the 2012 team had a winning record at the latest point during the season (Sept. 18), the 1999 squad entered their final three games with a 78-80 mark, so had they won out the Pirates' streak would have ended as a fairly unremarkable one. Alas and alack, that didn't happen.

Worst trade, 1993-2012

On July 23, 2003, Pirates GM Dave Littlefield dealt 25-year-old third baseman Aramis Ramirez and veteran outfielder Kenny Lofton to the Cubs in exchange for Bobby Hill, Jose Hernandez and Matt Bruback. This one did not turn out well for the Buccos. Ramirez went on to hit 275 more home runs (and counting), win a Silver Slugger, make two All-Star teams and notch three top-10 NL-MVP finishes. Lofton, meantime, went on to have another reasonably productive four-and-a-half seasons. As for the Pirates' end of things, Hill gave them the "most": 185 games spread across three seasons and an OPS+ of 82.

Best trade, 1993-2012

To be frank, Cam Bonifay didn't do all that many good things during his eight years as the Pirates' GM, but on November 18, 1998 he pried outfielder Brian Giles away from the Indians at a cost of lefty reliever Ricardo Rincon. Rincon gave the Tribe some reliable innings, but Giles had a weapons-grade four-and-a-half seasons in Pittsburgh: .308/.426/.591 with 165 homers and a pair of All-Star appearances.

And with their first-round pick, the Pirates take ...

As the Rays and Nationals have learned in recent years, the cold comfort that flows from being awful on the field is a glut of high draft picks. However, it's on the afflicted organization to do something useful with those picks.

As it turns out, the 1993-2002 period yielded 15 top-10 picks for the Pirates. In some cases, it's too soon to pass judgment, but with the remainder we can do precisely that. So let's take a look at how they spent their king's ransom of top-10 picks over the years.

We'll take a look at each choice, list the draftee's career WAR to date in the majors and then run down other, perhaps better choices that were still on the board. With the "still available" category, we'll limit it to players chosen within the next 10 picks. It's a bit unfair to, say, pluck a draftee from the 10th round who panned out because, frankly, no other team was on to him, either. Keeping it to within 10 picks of the Pirates' choice means we're generally looking at players of similar regard in terms of pre-draft evaluations.

Remember, we're looking at just the top-10 picks the Pirates exercised from 1994 (the first draft linked to the 20-year drought) onward. In bold, you'll see the draft year followed by the overall pick, the name of the Pirates' draftee and his school. Onward ...

1995 - #10: Chad Hermansen, SS, Green Valley HS (NV)
Career MLB WAR: -3.6.
Still available: Roy Halladay (#17, Blue Jays)

1996 - #1: Kris Benson, RHP, Clemson U.
Career MLB WAR: 13.0
Still available: Eric Chavez (#10, Athletics)

1997 - #8: J.J. Davis, 1B, Baldwin Park HS (CA)
Career MLB WAR: -1.3
Still available: Lance Berkman (#16, Astros)

1999 - #8: Bobby Bradley, RHP, Wellington Community HS (FL)
Career MLB WAR: Never reached majors
Still available: Barry Zito (#9, Athletics)

2001 - #8: John Van Benschoten, RHP, Kent State
Career MLB WAR: -3.5
Still available: Casey Kotchman (#13, Angels)

2002 - #1: Bryan Bullington, RHP, Ball State
Career MLB WAR: -0.2
Still available: Zack Greinke (#6, Royals); Prince Fielder (#7, Brewers)

2003 - #8: Paul Maholm, LHP, Mississippi State
Career MLB WAR: 12.8
Still available: John Danks (#9, Rangers); Aaron Hill (#13, Blue Jays)

2006 - #4: Brad Lincoln, RHP, U. of Houston
Career MLB WAR: 0.6
Still available: Clayton Kershaw (#7, Dodgers); Tim Lincecum (#10, Giants); Max Scherzer (#11, Diamondbacks)

2007 - #4: Daniel Moskos, LHP, Clemson U.
Career MLB WAR: 0.2
Still available: Matt Wieters (#5, Orioles); Madison Bumgarner (#10, Giants); Jason Heyward (#14, Braves)

2008 - #2: Pedro Alvarez, 3B, Vanderbilt U.
Career MLB WAR: 3.3
Still available: Buster Posey (#5, Giants)

As you may have already surmised, the Pirates would probably like mulligans on most of these. There's no shame in the Alvarez and Maholm selections, and Benson wasn't a terrible choice considering the general underwhelming nature of the 1996 first round. The rest, though, should be viewed by the Pirates partisan with ever-mounting chagrin.

As for the more recent top-10 selections, it's too soon to say much with any certainty. Although the picks of Jameson Taillon (#2, 2010) and Gerrit Cole (#1, 2011) seem to be shaping up nicely.

Remembering "Operation Shutdown"

Intone the names on the drought-era rosters as though reading from a war memorial of solemn polished marble: Midre Cummings ... Keith Osik ... Tike Redman ... Josh Fogg ... Ian Snell ... Will Pennyfeather ... Rich Loiselle. Eventually, you'll come to ... Derek Bell.

Mr. Bell, signed as he was to a two-year, $9-million contract, entered spring training 2002 in a state of presumption. He did so despite, in the first year of the deal, having batted .173/.287/.288 and having missed more than 100 games because of knee and hamstring injuries.

It was the aforementioned Cam Bonifay who signed Bell to the deal, but it was the new GM, the aforementioned Dave Littlefield, who was tasked with doing something with him. So the Pirates that spring put Bell squarely in competition with fellow outfielders Craig Wilson, Rob Mackowiak and Armando Rios for two spots. Let it be said that Mr. Bell did not approve of this arrangement. His comments to the Pittsburgh Post-Gazette:

"Nobody told me I was in competition. If there is competition, somebody better let me know. If there is competition, they better eliminate me out of the race and go ahead and do what they're going to do with me. I ain't never hit in spring training and I never will.

"If it ain't settled with me out there, then they can trade me. I ain't going out there to hurt myself in spring training battling for a job. If it is (a competition), then I'm going into 'Operation Shutdown.' Tell them exactly what I said. I haven't competed for a job since 1991."

And with those words -- "Operation Shutdown," the vague threat of something or perhaps a demontrable lack of something -- Bell's Pirates tenure was forever cast as something more regrettable than regret itself.

Bell bolted camp before being officially (and inevitably) released. When a team functionary saw him packing his bags, he asked Bell if he had any parting words. ''I got onto my yacht and rode off into the sunset," said the author of Operation Shutdown.

The Passion of the McClendon

It's June 26, 2001, and Jason Kendall has just been called out on a close play at first. Pirates manager Lloyd McClendon steadfastly believes otherwise and goes to unusual and -- let's be honest -- outstanding extremes to make his point to first-base ump Rick Reed ...

Bold, beautiful stuff, especially for a rookie skipper. Of the first base bag in particular and his act of civil disobediance toward umpire Reed in general, McClendon said, "I told him he wasn't using it, so I thought I'd take it."

If you're so inclined, consider this your Official Board-Certified GIF of the Drought Years.

The "All-Drought" Team

Our sojourn would not be complete without an ad-hoc All-Star team. So let's assemble a Pirates team using the best players of the 1993-2012 seasons, during which all Bucco efforts came to grief ...

C - Jason Kendall, 1998
If not for the career-altering ankle injury he suffered in July of 1999, then Kendall might have cobbled together a Hall of Fame career. In '98, though, he was as good as he'd ever be: .327/.411/.473 with 26 steals in 31 attempts and more than 1,200 innings caught.

1B - Kevin Young, 1999
Young would later become something of a punchline after the four-year, $24-million contract extension he signed in spring training 1999 (the richest deal in team history at the time) turned into a boondoggle, but in that first season he was quite good: a 128 OPS+, 73 extra-base hits, 22 steals.

2B - Neil Walker, 2012
Current contributor! Last season, Walker authored a slash line of .280/.342/.426, hit 14 homers and played sound defense at the keystone. He edges out Freddy Sanchez in 2007.

3B - Aramis Ramirez, 2001
Before Ramirez was the centerpiece of the worst trade in the Drought Era, he was a promising young third baseman. In his age-23 season, he batted .300/.350/.536 and smote 34 homers and 40 doubles. He edges out ... Freddy Sanchez and his unlikely batting title in 2006.

SS - Jay Bell, 1993
In '93, Bell won a Gold Glove and batted .310/.392/.437, while the average major-league shortstop that year hit .266/.328/.362.

OF - Andrew McCutchen, 2012
Current contributor! 'Cutch had his breakout campaign last season, when he posted an OPS of .953, thieved 20 bases, played a nifty center and finished third in the NL-MVP balloting.

OF - Brian Giles, 2002
What a season it was for the aforementioned Giles. His OBP of .450 (!) ranked second to former Pirate Barry Bonds, as did his .622 SLG and 135 walks. Giles also chipped in 38 homers.

OF - Jason Bay, 2005
The year after his Rookie-of-the-Year campaign of 2004, Bay played in all 162 games and batted .306/.402/.559 (150 OPS+) with 335 total bases.

RHS - Francisco Cordova, 1998
Signed by the Pirates as a free agent out of Mexico, Cordova enjoyed his finest season in '98, when he notched a 3.31 ERA (132 ERA+, good for 10th in the NL) and worked a hefty 220 1/3 innings.

LHS - Oliver Perez, 2004
Perez fights off a stiff challenge from 1996 Denny Neagle. In '04, Perez, then just 22, pitched to a 2.98 ERA (143 ERA+) and struck out 239 batters in 196 innings.

CL - Joel Hanrahan, 2011
Hanrahan in '11 worked 68 2/3 innings, struck out 61, showed the best control of his career, and gave up just one home run all season. In related matters, he put up an ERA of 1.83 (203 ERA+) and saved 40 games.

***

And now, with the past disinterred and amply reflected upon, let us bury it again, forevermore this time. May you good Pittsburghers never walk these ghastly paths again.

In conclusion, Corsair rooters, remember the past but savor the present ...

(GIF: @JollyRogerBlog)

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