Pittsburgh Pirates: Examining When the Team Will Contend Again

While the 2020 season has been ugly, there is light at the end of the tunnel. The Pittsburgh Pirates might be back in contention sooner than you think.

The 2020 season has been rough for the Pittsburgh Pirates. They’re off to a 4-15 start to the season. In the long run, it’s not such a bad thing considering they’re on pace for the #1 overall draft pick in 2021.

Whether they chose Kumar Rocker or Jack Leiter remains to be seen. They’ll for sure pick whoever out of the two Ben Cherington sees as the best long term option, as the Pittsburgh Pirates haven’t been afraid to throw around money before at prospects. After all, they own multiple of the highest paid prospect signing bonuses of all time.

But the Pittsburgh Pirates haven’t been in serious contention since 2015. It’s feels like forever ago when they were considered a true NL Central contender. But fear not. There is light at the end of the tunnel. So how much longer should it realistically be until the Pirates are ready for contention?

When looking at something like this, you also have to consider the state of other teams. One of the Pirates’ main rivals, the St. Louis Cardinals are going to lose a lot of their best players like Jack Flaherty, Carlos Martinez and Miles Mikolas in the 2023-2024 off-season. Kolten Wong is a free agent after the 2021 season, Matt Carpenter is a free agent after 2022.They’ll also still be under contract with Paul Goldschmidt, who will be 35 in 2023. Currently, they only have the 19th best farm system.

The Milwaukee Brewers are not going to be the threat they have been. Far from it by 2023 or 2024. While Christian Yelich, Brandon Woodruff and Keston Hirua will be around for a while, that’s about it currently on their roster. Josh Hader probably won’t be. He’s a free agent after the 2023 season, and he might not be with the Brewers by then. After all, there were a ton of trade rumors surrounding the lefty in the most recent off season. They also have probably the worst farm system. In all likelihood, they’ll be the ones in a midst of a rebuild by ‘23-’24.

The Chicago Cubs might also be in the midst of a rebuild by then as well. The Cubs are going to be set with many decisions by the 2021-2022 off season. If they haven’t already traded away, or extended some of their players, the Cubs will be set to see Kris Bryant, Javier Baez, Anthony Rizzo, Kyle Schwarber, and Jon Lester all hit free agency. Bryant likely won’t resign after his service time dispute, and Lester might retire. After all, he’ll be 37 by the end of the 2021 season. In the next off season, they might also see Willson Contreas leave, and Yu Darvish and Ian Happ the next off season. With the 22nd worst farm system in baseball, a rebuild could be in the Cubs future.

The Cincinnati Reds are the only team truly built for 2023, and possibly later. They have Sonny Gray, Eugenio Suarez, Luis Castillo and Mike Moustakas under contract through at least the 2023 season. Young and upcoming names like Nick Senzel, Hunter Greene, Aristides Aquino and Tyler Stephenson are all potential long term players for the Reds.

Good teams build their core from within, and fill in the cracks with pieces from the outside. The Pittsburgh Pirates have an extremely deep farm system to build that competition ready core. But they need to add pieces from the outside, and they absolutely will.

Just look at 2016 for example. The Pittsburgh Pirates had a $100 payroll, but had nearly $30 million owed to eight players that posted an fWAR under 1 each. Then in 2017, they had a pretty similar payroll, and owed about $22.625 million to five players who had less than less than 1 fWAR each.

The only player in those two years that the Pittsburgh Pirates didn’t acquire via free agency or through trade was Jeff Locke who was paid $3.025 million through arbitration in ‘16, so it wasn’t a lack of interest in pursuing free agents or trades. It was more of a lack of pursuing quality over quantity. Neal Huntington was known for going for quantity over quality, and this was yet another example of him using that philosophy. A really good example of this was during the 2015-2016 off-season. The Pirates opened the ‘16 season owing $17 million to Ryan Vogelsong, Jon Niese and Juan Nicasio. In comparison, Japan import, and 2016 3rd place Rookie of the Year finisher Kenta Maeda, made about $6 million less than the trio, and J.A. Happ making $7 million less than the trio. John Lackey, and Johnny Cueto both had similar salaries to what the three Pirates’ pitchers made together.

An optimistic view of the Pirates returning to competition is 2023. The Pirates rank as the 6th best farm system by FanGraphs. FanGraphs has been known to have one of the best prospect rankings, and one of the highest success rates in terms of what players become productive major league ball players. The Pirates have 9 prospects in the top 150, with 5 in the top 100. Liover Peguero ranks as the #101 prospect, and with Carter Kieboom, Evan White, and Sean Murphy on the verge of losing their prospect status, he’ll be in the top 100 very soon, giving them 6, top 100 prospects.

By 2023, we should start seeing the arrival of guys like Travis Swaggerty, Tahnaj Thomas, Nick Gonzalez, Peguero, Brennan Malone, Quinn Priester, Carmen Mlodzinski, and Mason Martin. Hopefully, by then, Oneil Cruz, Mitch Keller, Bryan Reynolds, Ke’Bryan Hayes, Cody Bolton, and young relievers like Nick Mears, Blake Cederlind, and Geoff Hartlieb are proven MLB players.

Each of these guys have an ETA per FanGraphs of either 2022 or 2023. But I think a more realistic view is 2024. Not every single prospect is going to be an All-Star, nor is every player going to come out of the gates swinging. It might take a year for some of these guys to get warmed up to the major leagues. However, overall,  we should see a higher success rate with the new regime compared to the old regime as we do know they are using different strategies to develop players, strategies that have proved to be more effective than what we saw previously.

Plus, based on Cherington’s track record, he knows how to oversee player development as he was the Red Sox assistant to player development for six years. He knows what players are talented, and what players aren’t, and how to develop them into productive major league ball players.

There’s light at the end of the tunnel. Even if not every single prospect turns out, they have such a deep farm system that they’ll be able to make up for it. Like if Swaggerty isn’t the complete package like he’s projected to be, the Pirates still have Jared Oliva, and could move someone like Ji-Hwan Bae to center. Plus if they have a $100 million payroll like they did in 2016-2017, they’ll be able to fill any holes with quality MLB players. Not only could they have an extremely effective MLB team by 2023 or 2024, but some of their rivals might be in the situation the Pirates are in now.