Looking Back At The Pirates’ Last Playoff Run

It’s been a while since the Pirates were relevant. Top Pittsburgh prospect Jameson Taillon was less than one year old when the Pirates last posted a winning record in 1992. A generation of Pittsburgh sports fans has had to rely on the city’s football and hockey teams for excitement. 

Some things haven’t changed in the last 19 years – members of the '92 Pirates like Miguel Batista, Tim Wakefield and manager Jim Leyland are still around – but it’s been long enough that we aren’t used to the possibility that Pittsburgh could be a buyer at the trade deadline. The 45-41 Pirates are now legitimately in contention, so it’s time to entertain the notion that GM Neal Huntington will be looking to add Major Leaguers rather than prospects this month.

The last time the Pirates made the playoffs, GM Ted Simmons completed a pair of midseason trades that helped deliver Pittsburgh to its third consecutive NLCS. First, Simmons sent minor leaguer Tony Mitchell to the Indians for speedy outfielder Alex Cole on July 4th. A week later, the Pirates sent third baseman Steve Buechele to the Cubs for left-hander Danny Jackson. 

Looking back, it’s easy to see that the deals helped Leyland’s Pirates to a 96-win season. But at the time, they weren’t considered blockbusters.

“I would consider them trades that no one was even paying attention to,” said Simmons, who is now a senior advisor to Seattle GM Jack Zduriencik. 

Simmons knew Cole as a strong defender who could get on base, and wanted to add him to a Pirates outfield that already featured Andy Van Slyke in center field and Barry Bonds in left. Cole became an everyday player for the Pirates, posting a .278/.335/.361 line down the stretch, and Mitchell, the prospect he was traded for, never made it to the Major Leagues. 

Jackson appealed to the Pirates, who wanted to add a southpaw to their rotation, yet Simmons wasn't completely confident in the left-hander's health. After scouting Jackson in depth, the Pirates were convinced that the former first rounder and 20 game winner had recovered from earlier injuries and regained his form. Fifteen starts later, Jackson had a 3.36 ERA with 4.7 K/9 and 3.0 BB/9 for Pittsburgh.

Though the deals worked out well for Simmons and the Pirates in 1992, circumstances could not be more different this summer. Few expected the Pirates to be in contention before this season and now that they have a chance to end their streak of losing seasons at 18, ownership may push for an attempt at a playoff run.

Huntington could follow Simmons’ example and make modest acquisitions for the pennant race, or he could even look to supplement his roster with splashier trades. As long as the Pirates continue contending, Pittsburgh’s current GM will have the support of one of his predecessors.

“Everybody’s rooting for the Pirates,” Simmons told MLBTR. “Everybody – including me."