Throughout the years the Pittsburgh Pirates have surely had their fair share of quality starting pitchers but having more than one top of the rotation level pitcher at the same time is a feat that has proved difficult since the introduction of free agency. Today, we’ll take a look at the closest the Pirates have come to putting it together and the success of the club the duos helped create.

1991 – Doug Drabek and John Smiley

John Smiley was a crafty left-handed pitcher who was, unlike many we will discuss, a homegrown talent. Making his debut in 1986, John didn’t really get his footing until his 13-win season in 1988 as a starting pitcher. You still wouldn’t confuse him with a top end starter, but he was starting to show the tools and, more importantly, the potential. 

Doug Drabek made his MLB debut for the Yankees in 1986 and was traded that off-season in exchange for centerpiece Rick Rhoden. Drabek’s best season was 1990 where he won 22 games and the Cy Young award, but the two would put it all together in 1991 when Smiley won 20 games and Doug 15. Despite the win totals, Doug still outpaced John with a 2.76 ERA compared to Smiley’s 3.08. The tandem didn’t last as Smiley was traded to Minnesota in an almost pure salary dump, but for two summers, they were one of the most feared combos in the game and led the Pirates to 2 of their 3 early 90s division championships.

2013 – AJ Burnett and Francisco Liriano

Two solid starters. That’s what they were really. Neither were ever stellar in their careers but each had tasted greatness in small doses for other organizations. By far, Liriano had the better season in 2013 but AJ was the attitude, he set the tone that the whole team played off of and together they paced the NL Central along with rookie Gerrit Cole. Liriano put up 16 wins and a 3.02 ERA while AJ suffered from little run support posting only 10 wins and a 3.30 ERA. Together they were a lefty-righty one-two punch few were equipped to handle. Couple in a power pitching youngster looking up to AJ named Gerrit and it was a recipe for success. One that started building the foundation in 2012 before arguably the most epic collapse at the end of a season we’ve seen in these parts. 

Both of these pitchers struggled mightily prior to being moved to Pittsburgh via trade and free agency, and both finding their legs gave immediate credence to Ray Searage being a reclamation specialist and Neal Huntington being an expert at identifying players primed for a rebound. It could be argued these two pitchers are more responsible for the management team under Neal surviving until the end of the decade than anyone.

2015 – Francisco Liriano and Gerrit Cole

The Pirates won 98 games in 2015, and pitching led the way. AJ Burnett had just left via free agency in 2014 for Philadelphia in an effort to play closer to where his family lived, and of course if everyone is honest, to cash in on the success he forged in Pittsburgh. But he lost 18 games for the Phillies and they declined to bring him back after the season leaving the door open for Batman to make a return to Pittsburgh which he promptly dubbed his final season. He was an important piece but Frankie and Gerrit were now the stars, especially Cole who showed everyone exactly why he was the number 1 pick. He won 19 games with a 2.60 ERA and dominated even more than the numbers showed. Liriano was fading a bit but still pulled together a 12-win season with a 3.38 ERA. 

During this time period there have been some classic duos throughout the league like Kershaw and Greinke, Verlander and Scherzer, Verlander and Cole, Scherzer and Strasberg. The Pirates have not been able to reach those heights and if the wild card games taught us anything it would be a good idea to have at least one. 

The near future doesn’t show a whole lot of moving pieces to create a duo like this, but the next time its possible would almost assuredly line up with Taillon returning and Mitch Keller entering his second full year hopefully on the upswing. This is probably the most tangible reason to target 2021 to see the next duo that could have immense impact. None of this means that 2020 can’t surprise us and have a couple guys emerge. It also doesn’t propose that Jameson will return at full speed and ready to recapture the form he was just starting to show prior to surgery.

The bottom line for the Pirates is really this simple, success for them and any baseball team is to have quality starting pitching lead the charge. That’s what history tells us, and that’s what common sense tells us. A small market team is hard pressed to get lucky and bring these types of talent in, Liriano and Burnett are not a typical occurrence in baseball. It's much more feasible to at least have one of them if not both be homegrown and the skillset is there for some of the current players to be in the mix, but someone would need to make a leap, a leap that reality wouldn’t dictate plausible. The options are right in front of the Pirates. First, they can wait and develop the players internally, if they miss on Keller or Taillon it’s a long trip to Priester. Next, they can sign someone, someone who is maybe a level below the top tier and hope for their career to emerge or takeoff here in Pittsburgh.

I can’t tell you when the Pirates will return to the playoffs, but rest assured when they do, there will be a dynamic duo leading the way. Who might they be?

Follow Gary on Twitter: @garymo2007