Williams: When Do You Expect the Pirates to Make the Playoffs and How Often Will They Return?

When do you expect the Pirates to win again?

I think we can all agree that 2021 isn’t in the cards. While I like the signings of Tyler Anderson and Todd Frazier from the perspective of building value inside the organization, I don’t think those two will be enough to take this last place team back to the playoffs.

On Friday, I wrote about how there is a window to contention opening starting around 2022, likely making the Pirates contenders around 2023, and extending for as long as their player development will allow. If I’m making a safe bet, I’d have the Pirates returning to a contending team in 2023.

That’s a reasonable expectation when you assume that Ben Cherington should have better results than Neal Huntington. When Huntington took over, he inherited a last place NL club with a very weak farm system. Cherington took over a last place team with a better farm system. It took Huntington five full seasons before he got the Pirates to the playoffs, and three full seasons before he got them in the discussion.

If we expect better results from Cherington, then we should be expecting him to reach the playoffs after about three seasons. By comparison, that would equate to Huntington reaching the playoffs in 2011, which may have been possible with better 2008 and 2009 drafts, and a better farm system in place.

Three seasons under a rebuild would cover 2020-2022, putting the Pirates in that window to contend again in 2023.

Under the Huntington timeline, Cherington wouldn’t have a contending season until the 2025 season, which isn’t acceptable, as that timeline essentially wastes all of the young players who have been retained to the current roster. Players like Bryan Reynolds and Kevin Newman would be free agents following the 2025 season, while Ke’Bryan Hayes and Mitch Keller would be approaching free agency, assuming no extensions.

The 2023 season seems like a bar for Cherington’s progress. If the Pirates aren’t back to the playoffs by that point, something has gone wrong. If they return to the playoffs in 2022, things have gone very right.

But what about when the Pirates return to the playoffs? How long do you expect the window to remain open?

Huntington made the playoffs three years in a row. That followed two years where the Pirates weren’t really contenders, but were technically still in it around July. This stretch was followed by three years where the Pirates were similarly in it every July, then out of it by September. In the eight year stretch from 2011-2018, Huntington had four winning seasons, three playoff appearances, and added at the deadline in the four years when the Pirates weren’t winning — typically adding for future years.

What do you expect in the eight years between 2023-2030?

I think we can set a bar of three playoff appearances as the minimum expectation for Cherington to be an improvement over Huntington. This might not be the expectation for most Pirates fans. In a limited poll a few weeks ago, I asked how many playoff appearances fans expected from Cherington over the next ten seasons. Almost 88% of the responses expected three or fewer playoff appearances, which would be a pace that would only match Huntington’s progress.

I think it would be disappointing if Cherington only matched Huntington. When Huntington took over, the Pirates were depleted in a lot of ways. I mentioned the poor drafts from 2008 and 2009. Huntington overhauled the entire scouting department by the 2011 draft, and was seeing much better results going forward. It should be noted that Cherington has maintained that department so far, while spending more time overhauling the player development side, which is where Huntington left the system lacking.

Huntington elevated the Pirates. It will be Cherington’s job to elevate them further. That means the expectation should be making the playoffs quicker than Huntington, and making it more often than Huntington.

So, when do you expect the Pirates to make the playoffs? And how often do you expect them to return?