I've looked at historic trades before. I'll probably do so in the future as well. However, this trade look is a trade look with a bit of a twist. Would the Cubs have traded Rafael Palmeiro before the 1989 season if the National League had the designated hitter at the time?
Palmeiro was a first-round draft pick for the Cubs in 1985 from Mississippi State. Teammates in school with Will Clark and MLB closer Bobby Thigpen (who was a two-way player in college), that was a fun team to watch mash. Palmeiro's only full season with the Cubs saw him earn an All-Star appearance. However, the emergence of Mark Grace led to a difficult decision. Neither was competent at any position but first base. The Cubs sent Palmeiro plus for Mitch Williams and others. The Cubs’ 1989 season was as rewarding as any over a long stretch of time. However, once Williams' wildness overcame his effectiveness, the Cubs had precious little remaining value from the trade.
Along with Williams, the Cubs added Curtis Wilkerson, Paul Kilgus, Steve Wilson, and a pair of players who never played in MLB. Wilson provided a degree of value to the Cubs as an international scout, particularly in the Pacific Rim. Palmeiro would hit over 540 homers after leaving the Cubs.
From a strict value perspective, the Cubs got shafted. However, National League teams had little room to keep two regular first basemen. I remember some grumblings about Palmeiro in the locker room. This isn't a comparison of Palmeiro to Mark Grace, as this article is acknowledging their incompatibility in a non-DH environment.
Baseball should be about locating and developing talent, irrespective of positions. While the fan's perspective is to have the team win as much as possible, the front office he's perspective is much more broad, and specialized. Some people are about the actual game on the field, others public relations, and others about things like talent location, or player development.
At some point reasonably soon, the romanticizing of the pitcher hitting will be available primarily in the "baseball history" section. Players coming through a pipeline will be treated similarly in both leagues if the bat is a little shy. The only outfielder the Cubs selected in the recently completed draft is Justin Nwogu, who hasn't displayed yet much ability to effectively play center or right field.
Accumulating talent en masse, nor developing talent for specific benefits, have been a historic Cubs strength. As to whether they've been "Top 10 in the league" in either category the past decade would be an interesting discussion. However, to be better than the other four teams in the division the next decade, it would make sense to acquire and develop talent better than the Brewers, Cardinals, Pirates, and Reds. To assess whether that's happening or not would require a degree of knowledge of how the other four are doing in comparison to the Cubs.
In the late 1980s, the Cubs were ushering out one of their better acquisition/development times in the past eight years. To make the next 20 years acceptable, guessing properly in free agency, and accurately assessing young developing talent will both be key tenets. The Cubs don't have many quality hitters in the upper minors, and they start at a disadvantage because of that. To win the 2020's, they need to develop and assess better than their rivals, whether through the draft, free agency, or trades, or a combination thereof. Accuracy is more useful than emotion to those ends.