79 wins

Good morning. It is September 1st,  2013.

With last night's win, the Pirates are 79-56. Since 1992, the Pirates failed to win 79 games in the following seasons*: 1993, 1994, 1995, 1996, 1998, 1999, 2000, 2001, 2002, 2003, 2004, 2005, 2006, 2007, 2008, 2009, 2010, 2011.

Let's not mince words: 1999 is the year that ruined everything. The Pirates took a step back after 1997's Freak Show, but in 1999 they had a lineup that featured Jason Kendall, Brian Giles, and yes, Al Martin and Kevin Young at the peak of their careers. The rotation had some young promise with Jason Schmidt and Kris Benson, and even Todd Ritchie and Francisco Cordova. With young players like Jose Guillen in Pittsburgh and Aramis Ramirez in the minors, this was supposed to be the group of players that lead the Pirates out of their post-Bonds-slump and into a new winning era of baseball at PNC Park.

For a while, it seemed like that's what would happen. They started 8-5 and they hung around .500 the whole first half of the season, getting as high as five games above it in June. That was good enough to keep them in the division and wild card race through most of June. They were still on the periphery of the race on July 4th. That's when disaster struck. Running out a bunt single, Jason Kendall turned his ankle over on first base and horrifyingly displaced it, popping the bone out of the skin and shearing all of the ligaments. Kendall was in the process of blossomming in 1999; he came up as a high-average guy without much power, but he homered 12 times in 1998 and already had eight homers at the time of his injury in '99. He was slugging .511 at that point, and heading towards a season that would make Andrew McCutchen jealous (his triple-slash line was .332/.428/.511). 

Instead, the Pirates lost him entirely and panicked. They traded the massively talented but difficult Jose Guillen to Tampa for catching help — Joe Oliver and Humberto Cota. Guillen had been badly mishandled by the club (they jumped him from Single-A to the Majors in 1997, which could have made him arbitration eligible in 2000 at the age of 23), but he was still one of their best young talents. That trade coupled with the Jon Lieber-for-Brant-Brown trade that had happened over the winter prior to the 1999 season. This all signified something terrifying: Cam Bonifay had put together enough talent to build a winning club, but he had no idea how to polish into something more.

Instead of having a young core of Ramirez and Guillen and Kendall and Giles to lead them into PNC Park, they ruined the development of both Ramirez and Guillen by calling them up at incredibly young ages. They'd given up on Guillen already and they'd irreparably started Ramirez's arbitration clock. Because the 2001 team was a listless wreck floating at sea with an incredibly young manager that was in way over his head (Lloyd McClendon was 42 in his first year on the job), Kendall was allowed to play through a debilitating thumb injury that sapped his power for the rest of his career. Lieber was in Chicago putting up great numbers, and the Pirates were in the process of giving up on Jason Schmidt and sending him to San Francisco to do the same. 

The pieces were all there in 1998 and 1999, but the Pirates let them slip through their fingers. Looking back, it was the Kendall injury and the Guillen trade that should've made that apparent. Instead of getting better, there was nothing but worse days ahead for these Pirates. 

There are still two seasons left to cross off of this list. This job is not yet done.

About Pat Lackey

In 2005, I started a WHYGAVS instead of working on organic chemistry homework. Many years later, I've written about baseball and the Pirates for a number of sites all across the internet, but WHYGAVS is still my home. I still haven't finished that O-Chem homework, though.