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I've been playing the Pirates in an on-line league, starting with the 2015 season. We just finished 2028. The individual games are necessarily managed by computer, so my experience is some indicator of how the team will perform if a human (albeit not a particularly skillful one) handles the GM tasks and the AI serves as manager.
My 2015 Pirates went 81-81, then steadily improved through 2020, when they finished first in the Central Division (92-70), swept the Mets in the NLDS and were, alas, swept by Los Angeles for the NL championship. (The Dodgers then lost to Texas, 4-1).
The ascent from 2015 through 2020 was followed a steady decline, down to 67-95 in the most recent season. (But that was better than 2027's 63-99, and we went 38-35 after the All Star break. Keep hope alive!)
The deterioration was pretty clearly due to Pittsburgh's perennial real-world problem: small budgets that make it impossible to compete for top free agents. Also, during the good years, our farm system weakened for want of top draft picks. Now we're in the process of rebuilding, which will probably require another couple of years.
While your performance so far may just be bad luck, I suggest taking to heart the suggestion that your managing skills need sharpening and would try to improve there before embarking on clever trades.
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