Even in "Ife Baseball Integrated Early," there's not a lot of help. The leagues are so much different anyway it's not really fair to compare, but the Cubs are still the Cubs.
That beings aid, 2003 looks good, but surprisingly, so does the mid- to late-1930s. They had good pitching and won 4 pennants in 10 years (1929, 1932, 1935, and 1938). In 1935 the lost to the Tigers in 6, and were swept by the Yankees in 1938, but if they'd outbid the yankees and managed to land Joe DiMaggio (they get Willard Brown in IBIE) they'd have a shot in '38 or in '36 or '37. Lefty Gomez couldn't pitch near as well away from Yankee Stadium and the rest, except for Red Ruffing, weren't that spectactular, IIRC. Heck even without Dimaggio, they might hve done something in '36 or '37.
The '45 club had the last 4 at home and only had to split, and lost 3 of 4. I put that in with '08 as a club that just had no confidence. Though it's still easier than '84 and '89, which saw A.L. clubs that were too tough, IMO.
There aren't a lot of other possiblities. The Orioles were also too good in '69 and '70 (if they could have beatent he Reds in '70, which I kidn fo doubt); yes the Mets beat the Orioles, but their pitching was just *insane* that year, int he last 40 games I think they had an ERA of about 2.00! The Cubs would have made it close but the Orioles had the home field, and personally, I think the Braves give them real trouble in the NLCS anyway.
lothaw, I remember that "Back to the Future" one, it would be comical if it happened then. They can't beat Miami, though, unles there's realignment.
Miami was expected to come in 3rd in OTL to Denver and Tampa. The POD might be Bill White not having the influence to prevent Tampa from getting an expansion club, as he disliked Tampa because of how he was treated there during spring training, IIRC. Then, with no expansion in '98, the 2 teams in biggest trouble at that time move - the Expos to Arizona and the Twins to Miami.