It may seem as if it has been decades since the Pittsburgh Pirates were half-decent, considering that as of now their roster is extremely bare. 

Sure, they have nice pieces in Ke’Bryan Hayes, Bryan Reynolds, and Adam Frazier (likely to get traded), but it would be safe to assume they have been in this rebuilding process for a while now. 

What many seem to have forgotten is the stretch of success the Pirates had in the mid-2010s. Historically, Pittsburgh has been cheap when it comes to their player payroll. 

According to Umpire Resources, the team has never been in the top half for player payroll since 1998. 

According to ESPN, their fan attendance during their playoff runs were around league average, meaning the correlation between fans showing up to games and cash flow was somewhat correct. 

For them to go on a three-year NL Wild Card game stretch is an impressive feat, especially when they were able to retain an MVP winner in Andrew McCutchen for almost a decade.

The not-so-impressive fact is that Pittsburgh only escaped the Wild Card round once. The lone time that they went to the divisional round, they lost. 

They missed the playoffs with a record of 78-84 in 2016. With an unwillingness to spend money on quality players, the organization’s only choice was to sell, and that they did. 

Now before this turns into “A Dynasty That Never Was” article, here is how the Pittsburgh Pirates sold off many players that could have formed an elite pitching rotation.

Robert Mayer-USA TODAY Sports

December 12, 2015: The First Domino Falls: Charlie Morton Gets Sent To Philadelphia

Phillies Receive: Charlie Morton (SP)

Charlie Morton, 32 at the time of the trade, could never find a consistent groove in his time with the Pirates. 

He had battled multiple injuries, and the season prior to getting traded, Morton posted a 4.81 ERA, 1.38 WHIP, 6.7 SO/9, and 2.9 BB/9. 

Another fun tidbit was that he led the league twice in hitting players with a pitch, and once in home runs per nine innings. 

The motive behind this trade was to shed off seven million dollars, while gaining a prospect in return instead of letting Morton walk for nothing. 

The season after the trade, the Phillies got four starts out of him. Philadelphia certainly did not get a ton of value out of the trade, but the Astros took a chance on the inconsistent pitcher once he hit the market. 

All he did with Houston was win a world series along with making an all-star appearance.

Morton then went to Tampa Bay after two years. He finished third in Cy Young voting in 2019, along with having another all-star appearance. 

Pirates Receive: David Whitehead (P)

So, was David Whitehead anywhere near the running for a Cy Young award? 

Let’s put it like this, at the time of the trade, all the Pittsburgh Gazette wrote about him was “Whitehead, 23, was a 34th-round pick in the 2013 draft. He had a 4.44 ERA in 25 starts for Class A Clearwater in 2015.” 

This was not too promising of a breakdown, and neither were Whitehead’s stats in the minors after the deal. He never posted less than a 7.13 ERA. 

David Whitehead would be out of the MLB by 2017, never making it higher than Double-A.

WAR Differential After Trade: -12.9

thatlostdog-- on Flickr (Original version) 佾珜 (Crop), CC BY 2.0, via Wikimedia Commons

January 13, 2018: Gerrit Cole Heads to Houston

Astros Receive: Gerrit Cole (SP)

After two seasons of slightly below .500 seasons, the Pirates were looking for changes. Pittsburgh went with quantity over quality in this deal, after failing to send Gerrit Cole to the Yankees in exchange for Gleybor Torres.

In the season prior to the trade, Cole had a career-worst 4.26 ERA. 

This was not completely Cole’s fault, however. His SO/9 were still around league-average, and his BB/9 were lower. He had started a league-high 33 games in 2017, only drawing away a 12-12 record. 

He had improved in a few categories, and the only regression besides ERA was his HR/9, which had never been above a 0.5, jumped up to a 1.4. 

While the home runs given up had nothing to do with the team around him, many other stats worked negatively in his favor. 

The Pirates that year had finished 28th in runs while ranking below average in many defensive categories such as errors and fielding percentage (ESPN). 

Of course, errors do not count towards a pitcher’s ERA, but poor fielding still can. A down year overall for the team should not have made the Pirates trade their 26-year-old ace in the first place, but they still made the move. 

Cole Never looked back, and in the four years after the move to the Astros and later the Yankees, he had substantially better years than with Pittsburgh. Here are his accolades after the trade:

Pirates Receive: Colin Moran (1B), Jason Martin (OF), Joe Musgrove (SP), Michael Feliz (RP)

The easiest piece to dissect from the Pirates’ return is outfielder Jason Martin

He was not a regular in the lineup and contributed a negative WAR each year in Pittsburgh. Martin is now in the Triple-A with the Texas Rangers. 


Michael Feliz spent all of his years with the Pirates since the trade, until he got traded this year to the Cincinnati Reds. He was nothing special with his time in the steel city, leaving with a WAR in the negatives. 


The other two pieces in the deal were the ones where the Pirates received positive value, but nothing close to Cole’s worth. 


Colin Moran was the sixth overall pick in 2013, and with his four seasons with Pittsburgh so far, he has left mixed results. He has been a solid contact hitter while not offering much as a defensive third/first baseman. 

As for Joe Musgrove, the Pirates received more inconsistency. He was by no means bad, but the organization never knew what they were going to get whenever he started.

Musgrove also fell victim to what Cole did in Pittsburgh, which was a lack of run support in addition to poor defense. 

Former GM Neal Huntington likely still thinks about how he was unable to land a Top-100 prospect for one of the best pitchers in the MLB. He should have landed at either Kyle Tucker or Forrest Whitley at least.

WAR Differential After Trade: -14.8

July 31, 2018: Six Months Later, The Pirates Trade Tyler Glasnow for… Chris Archer?

Rays Receive: Tyler Glasnow (SP), Austin Meadows (OF)

Standing at 56-52 at the time, the Pirates were riding with momentum and believed that they could win the Pennant. 

“We believe in the young core that’s here, the young core that will be here for several years as we move forward and the wave that’s right behind them that we believe in,” said team president Frank Coonelly. 

The organization was confident where they were, so they moved two prospects away for a former All-Star who had already shown signs of regression. 

The Pirates had been using their prospect at the time, Tyler Glasnow, in a reliever role for part of the season. 

He had struggled a little, but at 24 years old, there was much more development ready to happen. 

Unfortunately for the Pirates, they tend to bail early on their players. Along with Glasnow, Austin Meadows was part of the deal as well. 

The same season he got traded, Meadows posted a .292 batting average along with a .795 OPS. That is not a bad line for his first taste of MLB action.

In 2019, Meadows made the All-Star Game while finishing 14th in MVP voting. The shortened 2020 season was the year that the Rays made it to the World Series with Glasnow and Meadows as two of their key pieces. 

While neither player has made much of an impact this year (Glasnow was on pace for a potential Cy Young Award before getting injured), both are still young, with room to grow, and possibly more World Series appearances left in the tank.

Pirates Receive: Chris Archer (SP)

The only way to describe Chris Archer’s two-year tenure with the Pirates is disappointing. He battled control issues, and only managed to win six games in 33 starts. 

It was enough for the Pirates to let him walk, and in this past off-season, Archer found his way back home to Tampa Bay. 

It should also be mentioned that in 2018 the Pirates did not make the playoffs. What a robbery by the Rays. 

“But we were able to bring in somebody [Chris Archer] who we believe can help push us forward this year and then help us in ’19, ’20, and ’21,” Coonelly said.

WAR Differential After Trade: -10.2

Rachel Getz on Flickr (Original version) 佾珜 (Crop), CC BY-SA 2.0, via Wikimedia Commons

January 19, 2021: Joe Musgrove Moves To Contender

Padres Receive: Joe Musgrove (SP)

This trade along with the next one are too early to judge, but it is important to still discuss the return for the Pirates, along with the players they gave up. 

A short tenure in Pittsburgh, Joe Musgrove was moved to a contender, and not too soon after, tossed the Padres’ first no-hitter in franchise history. 

He is not an ace, but a valuable piece in a potential championship-winning team’s rotation.

Pirates Receive: Hudson Head (OF), David Bednar (RP), Omar Cruz (P), Drake Fellows (P), Endy Rodriguez (C)

Reliever David Bednar is the only player from the Pirates who has made it to The Show so far and has been a solid piece in 2021, pitching for a 3.60 ERA in 34 games. 

Outfielder Hudson Head is 19 and has shown flashes of being an impact player once he makes it to the MLB. 

Pitcher Omar Cruz recently got called up to Double-A after two solid seasons in Single-A. Fellows and Rodriguez are two long-shots, but who knows, crazier things have happened.

WAR Differential After Trade: -1.4

Matt Brandi on Flickr, CC BY-NC-ND 2.0, via Flickr

January 24, 2021: Jameson Taillon Heads to The Bronx

Yankees Receive: Jameson Taillon (SP)

The Yankees needed to improve their rotation in the 2020 off-season and bought low on Jameson Taillon

Up to this point, he has been inconsistent, but keep in mind that he has not played an MLB game since 2019. The jury is still out on Taillon.

Pirates Receive: Miguel Yajure (P), Roansy Contreras (P), Canaan Smith (OF), Maikol Escotto

As of now, there is not much to talk about on the Pirates’ end of things, receiving prospects from the Yankees all ranked in between 15-21 besides Maikol Escotto

It was not a bad return for a player they did not want to pay.

WAR Differential After Trade: -0.3

The case for selling off key pieces when an organization is justifiable, especially when the said team consistently finishes close to last when it comes to money coming in. 

What cannot be ignored in this instance is that the Pirates sold off players that should have garnered much more value, not gaining the appropriate return. 

Patience is another factor that Pittsburgh had very little of. If they waited one more season, the possibility of Cole or Glasnow blossoming into Cy Young contenders would become a reality. 

The “Moneyball” strategy has proven to work, but it takes competent ownership along with the right staff hirings to pull off a successful low-budget team.