Perhaps no team in history defined a single decade like the Bulls of the 90s. They racked up wins, fans, championships and pop-culture adulation on their way to immortality, ultimately etching a lengthy run of dominance that none of us may ever see again. Hence the 10-episode documentary The Last Dance that wrapped up last week.
Surely, there will be more such productions to showcase the greatest teams ever. Even before pandemic life took over, ESPN’s The Last Dance was easily one of the most anticipated television events in recent memory. Airing with no live games on, the entire sports world was firmly in its grasp for two hours every Sunday night.
That’s cool and all, and it’s academic for people to talk about which dynasty should be on deck for its own feature presentation. But damn it, some of us want to see the other end of the spectrum.
What about the perennially shitty teams that lost year in and year out for an entire decade? They were memorable, too. How did those players show up every day knowing it hopeless? What characters emerged out of that rubble?
See — there are fascinating queries to these cellar dwellers. Now which bottom feeder do we choose for such an honor?
The 2010’s might conjure thoughts of the Sacramento Kings, Miami Marlins and Cleveland Browns — the only organizations without a single winning season for the decade — but all three were respectable for at least one year within this span.
I want to find a franchise that truly lived and breathed losing. That entered each campaign with a hopeless roster and was poorly run. With the annual expectation to suck alongside the worst of the league. Going back another decade, I found what I was looking for in the Pittsburgh Pirates of the 2000s.
Of course, this particular 10-year batch of undesirable records, which also involved the glitz and glamour of brand-new PNC Park, would be part of a much bigger plot. One that saw the Bucs notch an incredible 20 straight losing seasons in all from 1993-2012. That’s the longest such streak ever in American professional sports, and much like the Bulls in their glory, it probably won’t ever be duplicated.
For the duration of the decade, the Pirates remarkably never finished higher than fourth place in the then-six-team National League Central. Even finishing as high as fourth was a difficult task, only doing so twice. They were so consistently terrible that they failed to produce a record that was 10 games within .500 (their best mark was 75-87), losing more than 90 games in all but two of those years.
I mean, imagine being a fan. Every goddamn season is inevitable pain — what’s the point of even following? You’re just bracing for six months of another lost campaign, another Summer shredded. It can’t be a good feeling.
But even in this losing culture, there was still an intriguing cast donning the black and yellow. Characters capable of making regular defeats at least a little more fun.
Completely opposite of how the Bulls entrusted Phil Jackson for nearly all of the 90s, the Pirates employed a handful of managers. The man who helmed this sinking ship longest in the decade, Lloyd McClendon, was a character in his own right. Who will ever forget in 2001 when he got ejected from a game and then stole first base? Yes, as in pried the actual bag out of the ground and walked off with it.
“I’ve never seen anything like that before and also I was laughing pretty hard,” said Jimmy Anderson, the starter that game who described McClendon as “intense” and “confrontational.”
Starter Jeff Karstens remembers being traded from the Yankees to Pittsburgh in 2008, and being banished to the bullpen the next season.
“Walking to the pen [there are] fans with bags over their heads with ‘trade me, too’ written in sharpie,” said Karstens. “I couldn’t believe it. Coming from a team where they loved everybody to one that felt a lot of hate towards maybe the front office, but the players played in front of all of them.”
There was no Jordan or Pippen to carry the offense. Not even close. Instead, it was Jason Bay and Brian Giles who cranked out more homers and RBI for the Pirates in the 00s. Aramis Ramirez was good, too. Jack Wilson served as the organization’s Derek Jeter at shortstop, amassing more games and hits than any Bucco throughout the decade. It was either he or Jason Kendall — the ultra-rare leadoff catcher — that could be considered the heart and soul of the club.
Freddy Sanchez deserves proper remembrance for representing the Pirates in the All-Star Game more than anyone else, and even winning a batting title in 2006. Randall Simon is another name you might recall, but more so for hitting a sausage mascot with a bat during the traditional sausage race in Milwaukee and getting slapped with a misdemeanor battery charge and a $432 fine.
Yes, that did happen.
Let’s remember some obscure hitters: Rob Mackowiak. Pokey Reese. Tike Redman. Craig Wilson. Humberto Cota. Believe it or not, the batting order also at one point contained the likes of old-timers Kenny Lofton, Benito Santiago and Raul Mondesi at the very end of their respective careers.
Hell, Jose Bautista got his start on these teams. The Pirates were so cursed back then that even Joey Bats looked like a mere mortal, before breaking out in Toronto and finding super stardom and majestic bat flips years later (before taking a stiff right hand to the jaw from Rougned Odor).
Later in the decade, they had their own Dennis Rodman in the form of Nyjer Morgan, whose camaraderie also involved his alternate alias of Tony Plush. He was a polarizing personality, to say the least.
Former Marlins color commentator Tommy Hutton once declared on the air of Morgan, “This guy has some serious problems.” Considering T-Plush has shit in Gatorade bottles and lost his shit on the field during live play, Hutton isn’t exactly wrong. There was also the time Morgan connected on a walk-off knock and didn’t even realize his team had won the game.
Like Rodman, Morgan was adored by those on his side. Former Pirates first-round draft pick John Van Benschoten called him “by far” one of his favorite teammates ever.
“I loved that guy,” said Van Benschoten. “He’d run through a brick wall for every single teammate no matter if it was in the MLB or [in the minors in] Hickory, N.C. “By far one of my favorite teammates I’ve ever had.”
Regular power threat Garrett Jones exclaimed there was no turning him off. He was the precursor to the savior of the franchise that would arrive in 2009, Andrew McCutchen.
Oh boy and the pitching. It wasn’t pretty. Pittsburgh’s top-five wins leaders in the 00s consisted of Josh Fogg (39 wins), Paul Maholm (38 wins), Zach Duke (37 wins), Kip Wells (36 wins) and Ian Snell (33 wins). Place that pitching staff in any era of Major League Baseball and the result is another 90-loss showing.
Kris Benson was also a staple in the club’s pitching rotation. That meant his crazy ex-wife Anna was part of the fray and who knows what chaos she caused there? When Kris played in New York, the former stripper said on Howard Stern she’d sleep with everyone on the team if she caught him cheating on her. That may or may not have foreshadowed a bulletproof-vest-wearing Anna pulling a gun on Kris years later after he filed for a divorce.
The Pirates had a grand total of one starting pitcher — one!! — make the All-Star team for the decade. That was Duke, and here’s the punch line: He would become the only pitcher ever to make the Midsummer Classic and ultimately lead the league in losses in the same season.
“In my three years there I had three different coaching staffs. None better or worse than the other just that they were all different,” said Van Benschoten. “There’s really no hiding it but I was pretty terrible.”
The one Bucs reliever to receive an All-Star nod in these years, Mike Williams, made it twice. His 2003 berth is infamously known as the one time in major league history that someone made an All-Star team with an ERA north of 6.00. He also humorously had more walks than Ks.
Let’s remember some obscure pitchers: Todd Ritchie. Francisco Cordova. Scott Sauerbeck. It’s no wonder how failing became a way of life in the Steel City.
The losing got so bad that, according to former Bucs hurler Jeff Karstens, a player once took his frustrations out on the TV he was watching with a bow and arrow.
“Losing got so bad, a player said I’m tired of hearing this thing and shot a bow and arrow through the television one night after a majority of the team had left,” said Karstens. “This was pre-Gilbert Arenas (who kept a stockpile of guns in his locker while playing for the Washington Wizards and famously pulled one on a teammate), and guys having their bows at the field wasn’t unusual. They usually would shoot on the field before anyone arrived.”
The TV was replaced the next day, with the player coughing up the dough.
“There are tons of stories that range from G [rated] to unknown ratings to tell,” said Fogg.
Just consider it as more fuel to the fire why we need documentaries on the worst of the worst. That parallel universe NASA discovered may already be rolling them out.
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