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PITTSBURGH: The Pirates had just returned home from an eight-game losing streak last week. The usual gaggle of scouts could be found sitting in the seats behind home plate at PNC Park watching the home team face the Cardinals. The skid had dropped the Pirates seven games under .500 and seemingly on their way to a 17th consecutive losing season, which would break their tie with the 1933-48 Philadelphia Phillies for the longest stretch of sustained futility in major American professional sports history.

Among the scouts watching that night were Cam Bonifay, working for the Reds, the Cubs‘ Dave Littlefield, and Roy Smith of the Blue Jays. This was more than a little ironic. Bonifay took over as the Pirates’ general manger for Ted Simmons midway through the 1993 season. Littlefield replaced Bonifay midway through the 2001 season and stayed on the job until being fired late in the 2007 season. Smith served as the assistant GM under both Bonifay and Littlefield. Thus, nobody has been more responsible for all of the losing, which began in ’93, than this trio.

It is now the charge of club president Frank Coonelly, GM Neal Huntington, and manager John Russell, who are in their second season running the club, of digging out of a hole just slightly more shallow than the Grand Canyon. The Pirates have few impact players on the major league roster, and even fewer top prospects in the farm system following years of drafting on the cheap and ignoring the international free-agent markets.

While the moves of Bonifay and Littlefield became laughable at times, the moment that signaled the start of all the losing was a heartbreaker. The Pirates won three straight National League East titles from 1990-92, quite a turnaround for a franchise that nearly left town in 1985 until Pittsburgh mayor Richard Caligiuri put together a public/private consortium to buy the club. However, they failed to make it to the World Series in any of those three division-winning seasons, and the final defeat was incredibly difficult.

That was the game in which the Braves scored three runs in the bottom of the ninth inning of Game Seven of the 1992 NLCS to rally for a 3-2 victory. Popular former ex-Pirates first baseman Sid Bream (who still lives in Pittsburgh) slid home with the winning run ahead of Barry Bonds‘ throw. The winning single was hit by a nondescript bench player named Francisco Cabrera off of Stan Belinda, a fresh-faced reliever who grew up in rural Port Matilda, PA, dreaming of pitching for the Pirates in the World Series.

Bonds left as a free agent after that season and so did ace pitcher Doug Drabek, a year after slugger Bobby Bonilla bolted and 20-game winner John Smiley was traded before he could follow suit. In their stead, the Pirates hoped to rebuild quickly around a number of young players: first baseman Kevin Young, second baseman Carlos Garcia, left fielder Al Martin, left-handers Steve Cooke and Denny Neagle, and knuckleballer Tim Wakefield. All except Neagle and Wakefield turned out to be journeymen, and the Pirates released Wakefield in 1995 during spring training, deciding that Wakefield had lost the feel on his knuckler. Of course, he is now in his 15th season as a mainstay of the Red Sox‘s rotation.

Releasing Wakefield was just one of many bad personnel decisions made by Bonifay. Another doozy came in 1999, when he signed infielder Pat Meares to a four-year, $15 million contract extension. Meares already had sustained a wrist injury that robbed him of what middling power he possessed. Furthermore, Meares had been so lightly regarded after being released by the Twins the previous winter that the Pirates were the only team to offer him a big-league contract as a free agent. It was no wonder he had a look of amazement following his signing of the four-year deal. “This really surprises me,” he said.

Bonifay’s last stand came at the 2000 Winter Meetings in Dallas. Knowing they would have a bump in revenue with the opening of PNC Park in 2001, the Pirates decided to be players on the free-agent market. The problem was that they gave much of their money to washed-up outfielder Derek Bell, who became a monumental bust and half-stepped it through only one season of his two-year, $9.75 million contract. Making matters worse, manager Lloyd McClendon said the Pirates “sent shock waves through baseball” by signing Bell. McClendon apparently missed that the Rangers lavished a then-record $252 million on Alex Rodriguez at the same meetings, while the Rockies spent $173 million on Neagle and fellow lefty Mike Hampton. The only thing shocking was Bell’s horrible performance. He hit .173 in 46 games in 2001, and was released the following spring after infamously telling a reporter he would go into “Operation Shutdown” if he was not the right fielder on Opening Day.

After Littlefield, Bonifay’s replacement, had jettisoned Bell, it was almost all downhill, as his tenure was fraught with so many awful player moves that he made Bonifay look like Branch Rickey. Littlefield’s last move was his most costly as he inexplicably traded for Giants right-hander Matt Morris, who was clearly on his last legs. The Pirates took on $13 million by acquiring Morris. For that money, he won three games in 16 starts before being released by Huntington early last season.

There were plenty of other gaffes, none more publicly humiliating than when five of the first six players taken in the Rule 5 draft at the 2003 Winter Meetings in New Orleans were Pirates. A ballroom full of baseball people broke into laughter over that. Also in 2003, the Pirates placed promising young pitcher Bronson Arroyo on waivers and he was claimed by the Red Sox. Three years later, while pitching for the Reds, he was selected to the All-Star Game. Fittingly, the game was at PNC Park, and Arroyo was booed during pre-game introductions. “I didn’t take it personally,” Arroyo said of the fan reaction. “They were just booing because the Pirates are the most inept organization in baseball.”

Not every player was down on Littlefield, however. He signed Jeromy Burnitz to a one-year, $6.5 million contract as a free agent prior to the 2006 season; the veteran outfielder sleepwalked his way to a .230 batting average and then never played again. Burnitz approached Littlefield as the GM walked through the clubhouse on the final day of the season and enthusiastically shook his hand. “Dave,” Burnitz said, “I can’t thank you enough.”

Even Bream returned to the Pirates last season as the hitting coach with their short-season A-ball State College team in the New York-Penn League. Part of the reason he came back was to help exorcize the ghosts of losing, a haunting that began when he slid across home plate that fateful night at Fulton County Stadium in the latter days of the original George Bush administration. “I’d like to try to help change things,” Bream said.

State College went 18-56 for the worst record in professional baseball. Beaten down by the losing, Bream chose not to return this year.

A version of this story originally appeared on ESPN Insider Insider.

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dianagramr
5/22
Dogpiling on the list of bad moves:
July 23, 2003: Pirates deal Aramis Ramirez, Kenny Lofton and cash to the Chicago Cubs for Matt Bruback (minors) and Jose Hernandez. The Chicago Cubs sent Bobby Hill (August 15, 2003) to the Pittsburgh Pirates to complete the trade.
tmangell
5/24
Cardinals fans everywhere rue that trade! A-Ram scares me everytime he comes to the trade against the Redbirds!

BTW, good article, but perhaps the crowning achievement in recent Bucs history is PNC Park. Affordable, great food and micro-beer selection!
cchatham
6/12
I still think that lists as one of the worst trades in Pirate history. Of course, Littlefield now works for the Cubs.
mhixpgh
5/22
Thanks. And loooooooooong overdue. This really sums up what it has been like to be a baseball fan in Pittsburgh the past 17 years. The Penguins and the Steelers are professional and VERY well-run organizations. The Penguins and Steelers compete for playoff spots and chanpionships. The Pirates.... simply a laughingstock.

Let me be more specific: The Pirates have been a shameless laughingstock who have been reliant on bobbleheads, fireworks displays and a wonderful (publicly financed) ballpark to eek out a marginal profit each season.

I remember back in the 2000 season when the fans, rather than chanting "Let's Go Bucs", would chant "Trade Pat Meares". It was a true Jumping The Shark experience.

Question: Where were Bob Smizik, Gene Collier, Dejan Kovacevic, John Perrotto and the rest of the sportswriters in Pittsburgh while the Pirates were perpetrating this fraud on their fans?
georgeforeman03
5/22
Seriously, what were those media-types thinking? Pittsburgh's ineptness is clearly a systematic failing of journalists, from the editor right down to the paper boy. I mean, just look at Atlanta! How can you lose when you've got Furman Bisher, Mark Bradley and Terrance Moore heading up your staff?
mhixpgh
5/22
Access too often buys silence. Journalists should be more than stenographers. Parroting the company line is enabling, not journalism.

I don't think journalists should be cynical, but a healthy skepticism would be nice. Too bad Jon Stewart didn't cover the Pirates that past few years.
perrotto
5/25
If you read ANYTHING I wrote during the Bonifay and Littlefield administrations, you'll know I was the first Pittsburgh media member to call for the firing of both GMs and also the most critical of their regimes. To say I toed the company line is completely false and I received more than one hostile phone call from Kevin McClatchy to prove it. Know what your talking about before making an accusation like that.
briankopec
5/23
Actually, local media (and the fan base) has at least some culpability as they acted as enablers. Every horrible free agent signing, middling prospect, and 5 game winning streak was touted as the turning point that would send the Pirates back to .500. The start of each season would herald a series of Post-Gazette articles explaining how this would be the year the Pirates got back to a winning record. Go buy those season tickets!!! PNC Park is opening up and we'll be able to keep our free agents (as if there were any worth keeping)!!!!

Meanwhile, roster decisions were based on how many more seats they'd sell when the move was pimped in the papers. Season ticket sales are declining? Jeremy Burnitz and Sean Casey are 2 guys the fans have heard of...let's throw money at them. Or Benito Santiago is a famous name, let's trade this live arm down in A ball for him, after all our fans have no idea who Leo Nunez is. Or let's draft the local kid, Neil Walker, in the first round...it'll make a great story! Of course, development of a winning team be damned.

And I can't blame them because the people kept coming. Of course, it is now a different kind of crowd. Baseball is a tertiary attraction at PNC Park, trailing behind at least whatever bobblehead is given away that night (Paul Maholm anyone?) and the wonderful views of the city skyline beyond the walls. Even when they stop coming, the Pirates can turn a profit almost exclusively on revenue sharing. An entire generation of potential baseball fans in Pittsburgh has been lost by these fools. Sure, if the Buccos ever contend again they'll draw fans. But the people in the stands will be fans of entertainment, not fans of baseball. There are few people between the ages of 8 and 30 with a true passion for baseball. That is the legacy of McClatchy, Nutting, Bonifay, and Littlefield.
mhixpgh
5/23
Amen!
hotstatrat
5/23
Yes, I enjoyed this team highlight and appreciated the added details from Brian Kopec. One detail is still missing, however. Who were those five Rule V draftees?
charlieva
5/23
Chris Shelton, Rich Thompson, Frank Brooks, Jeff Bennett and Jose Bautista. Thompson and Brooks were offered back to the Bucs and weren't any great shakes anyway. But Shelton had a couple of semi-productive seasons with the Tigers and would have been more useful and less expensive than Sean Casey or Daryle Ward; Bennett turned out to be a useful reliever; and the Pirates had to make an unfortunate trade to get Bautista back.

The Bucs also waived Duaner Sanchez and Matt Guerrier as part of that '03 Rule 5 roster purging.
briankopec
5/24
My recollection is that their waiving of Duaner Sanchez was not a baseball decision. That doesn't make it any better or any worse in my eyes. Just...different.
charlieva
5/23
Well, Kovacevic was covering hockey or something. In any event, he wasn't writing about the Pirates. So you can't really blame him. The main P-G writers before Kovacevic were Robert Dvorchak, who was pretty nondescript, and Paul Meyer, who tried to justify pretty much every poor move the Pirates made. Kovacevic showed a pretty firm grip on reality from the first day he took the job.
eighteen
5/23
Why would anyone hire Bonifay, Littleifeld, and Smith to scout talent? They wouldn't know talent if it slapped 'em in the face.
markpadden
5/23
I agree. This a very good article. And it merely touches the surface of the ineptitude of Littlefield. The man should never enter a stadium without a ticket again.
ironcityguys
5/23
The Pirates' downfall can legitimately be traced further back to the hiring of President Mark Sauer. The slimy executive not only fired two fine GMs (Larry Doughty and Ted Simmons) within 2 years, but subsequently turned the reigns over to the self-serving and inept Bonifay prior to bolting. It was the combination of Sauer and Bonifay that greased the skids for what has happened since then.

Some of us remember the Pirates having the best record in baseball, the train belching smoke on the scoreboard, Wake flipping his knuckler, and a multitude of players enjoying their time in the 'Burgh (despite a bleak and bland home stadium). We remain hopeful that we live long enough to experience that level of excitement again.

Thanks for an excellent article, John.

IAPiratesFan
5/23
Correction: Ted Simmons resigned after having a heart attack in June 1993. Insert obligatory joke about how the Pirates gave him a heart attack.
szielinski
5/23
It's sad that, even when the Pirates seem to show a bit of life, as they have this year, they will again earn another top five draft pick in the next year's draft....

It is unfortunate that John P. failed to mention the biggest miscreant of them all: Kevin McClatchy. He should be given his due. How bad was McClatchy? The Nuttings -- surprisingly -- have managed to point the organization in the right direction. But McClatchy's leadership was so incompetent that it may take five years or more to repair the damage he and his people did to the organization. It will take much longer than five years to rehabilitate the team's sullied reputation.

Pirate fans did not deserve these idiots.
mhixpgh
5/23
"Pirate fans did not deserve these idiots". Well, those people who keep going for fireworks, bobbleheads etc. deserve the baseball the pay for, right? Or, as someone above put it, they deserve the entertainment they pay for.

I take my 10 yr old to see 2-3 games a year, when an interesting team is in town. But if the Pirates were a well-run organization, making good decisions, fielding a roster of major league players (you know, trying to win games... Competing for even the occasional Wild Card spot...) we would certainly buy some sort of season ticket package.

Maybe some day soon the Pirates will be worthy of support from baseball fans in the Pittsburgh area.
szielinski
5/25
"'Pirate fans did not deserve these idiots'. Well, those people who keep going for fireworks, bobbleheads etc. deserve the baseball the pay for, right? Or, as someone above put it, they deserve the entertainment they pay for."

But "those people" -- that is, Pirates' fans who go to PNC for Skyblast, Bobbleheads and other similar things -- do not include every Pirates' fan. As things now stand, the Pirates draw meager crowds for most games. I'd bet the team would have become bankrupt if it lacked income from MLB as a whole. You have already identified the reason for this: The organization has been content to "Drive for 75" for many of the last 16 years.
newsense
5/24
"...digging out of a hole just slightly more shallow than the Grand Canyon."

I think the problem with Littlefield and Bonifay was that they were trying to DIG themselves out of a HOLE". Perhaps Coonelly and Huntington should try CLIMBING?! :-)