Williams: Out of the Rebuild

I haven’t played Out of the Park Baseball since that brief time period when I ran simulations during the delayed 2020 season.

I don’t think I’ve run an OOTP season since 2019.

For those who aren’t familiar, OOTP is a baseball simulator, and is the best simulator for those who want to create the circumstances to simulate operating as a General Manager.

There are some obvious glitches that can be exploited from the fact the game is a computer simulation. However, the core concept is the same: Build a team by collecting talent through all avenues, aiming to put together a winner under your specific budget provided by ownership.

If I got back into the game today, I’m pretty sure there wouldn’t be an article on this site for at least four days. I’d return with a recap of how the 2026 Las Vegas Aces are doing since their expansion draft, and whether the Pirates improved during that time.

I’ve been thinking about OOTP recently, specifically in terms of how I generally go about a rebuild in that game.

My goal in the game is the goal I’ve dreamt about on this site for over a decade: Building a small market team into a regular contender.

That goal always goes the same way: Acquire as much talent as possible, add the best coaches to develop the prospects, and until the MLB team is winning, always be adding value and always be playing the young players.

I look at the Pirates, and I see the potential for the same approach.

Granted, it’s easy for most teams to check a few of those boxes above. The Pirates are obviously rebuilding, and that process involves acquiring as much talent as possible. When I think about how I do that in the simulation, I’m typically trading one guy for 4-5 prospects. The guy traded away definitely isn’t worth all of the prospects I’m getting back if they reach their potential. The A.I. General Manager across the trade screen accepts happily, because my scouts like these players a lot more than their scouts, or the national rankings.

Thinking about it, is that not what Ben Cherington has been doing?

In every trade that has been made by the Pirates in real life, the return has been a collection of players who the Pirates are seemingly trying to get before a realized breakout — one where the breakout becomes obvious by the stats being produced in games. The Pirates have done well so far getting a few breakouts in their first season of development under Cherington and farm director John Baker. The most notable players are Roansy Contreras, Liover Peguero, and Endy Rodriguez.

I guess you could say this is a standard approach. Every team is going to have their own scouting rankings, and every rebuilding team is going to spread their rebuild around to multiple prospects, in a buy-low/sell-high strategy.

You could also say that the approach above of constantly adding value is in full-effect for the Pirates. Otherwise, Jacob Stallings would currently be on this team. I can’t argue with the fact he’s gone, considering where this organization currently stands. It’s the exact same type of move I’d make in OOTP.

Here’s where my question comes in: How can the Pirates get out of the rebuild?

I think that playing the young players is the best approach. The Pirates have been aggressive so far in their promotions of prospects to the majors, at least in comparison to the previous front office, which had a very strict, linear path for such promotions.

At some point, those players will need to adjust to the majors, and go through their struggles, just like we’ve seen with so many other prospects-turned-big leaguers. It would be much better for the Pirates if most of those prospect struggles took place in 2022 and the early part of 2023.

I think the Pirates can win in 2023, and should be winning by 2024. If the prospects like Oneil Cruz, Roansy Contreras, and others who arrive this year do well, then 2023 could be within reach with a good offseason next year.

Either year is a long way from when they last contended in 2015, or even from when they last had a winning season in 2018.

The hope this time around is that the current rebuilding efforts by Cherington, plus the improvements to player development under Baker, will keep them as contenders for a longer period of time.

Perhaps there will be a point in the future where a Pirates small market dynasty can exist outside of the OOTP Universe.