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Beginning in 1977, there was a steady stream of players whose primary association (or greatest fame) was with the Cubs inducted into the Hall of Fame in Cooperstown:
1977 Ernie Banks 1979 Hack Wilson 1987 Billy Williams 1991 Fergie Jenkins 2005 Ryne Sandberg 2010 Andre Dawson 2012 Ron Santo
If you expand this list to include Greg Maddux (2014), whose best years were in Atlanta but who still brought a lot of Cubs fans to his Cooperstown induction, and broadcasters Jack Brickhouse (1982) and Harry Caray (1989), winners of the Frick Award, that makes 10 Cubs-related people who gave speeches on Induction Weekend and brought many Cubs fans to the ceremonies over the last 38 years.
When will that happen again? I'm here to tell you... not anytime soon.
Dawson retired after 1996 and Sandberg after 1997. There are two Cubs-related players remaining on the active BBWAA ballot: Lee Smith and Sammy Sosa. Smith will be in his final year of eligibility in 2017 and Sosa has six more years on the writers' ballot (assuming he continues to get five percent or more of the vote, not guaranteed by any means). Neither seems anywhere close to getting enough votes for induction.
Players who made somewhat of a name for themselves on the Cubs in the first decade of the 2000s aren't going to make it either. For example, Kenny Lofton and Jim Edmonds fell off the ballot quickly and neither one played even one full season with the Cubs.
Among the better Cubs players of the decade preceding this one are Derrek Lee and Aramis Ramirez. D-Lee was certainly a fine player for a number of years, but he's nowhere near Hall-worthy. He'll be on the ballot for the first time next year, but very likely will fall off after 2017. A-Ram... well, I suppose there's a possibility. As a third baseman, he's in a group that's under-represented in the Hall, and he did hit 386 career homers and had over 2,300 hits. But he never led his league in any significant offensive category, he made the All-Star team only three times, and finished in the top 10 of MVP voting once (and the latter, not as a Cub; it was in 2012 with the Brewers). Ramirez will first appear on the ballot in 2021.
Alfonso Soriano will appear on the ballot beginning in 2020. He had some fine seasons as a Cub, but most of his best years were elsewhere, and I suspect he also falls short of Hall induction.
Then there's Lou Piniella. Had the Cubs won the World Series when Lou was manager, that probably would have put him over the top, given his very good playing career and the other World Series title he won with the Reds. Points in his favor include that playing career, during which he was a key part of five playoff teams and two World Series winners, and his 1,835 managerial wins, 14th all-time. Every manager with more wins is in the Hall, except Gene Mauch, who had a losing managerial record overall and never won a World Series.
So Lou might get in someday. Would that bring a lot of Cubs fans to Cooperstown? I tend to doubt it, as he was much better-known as a Reds and Mariners manager.
Thus we might have to wait until someone from the current young group of Cubs puts together a stellar career and qualifies for the Hall. But that could be 25 years from now, in fact, it would almost have to be, since a young player now would have to put together a career of 18-20 excellent years plus the five-year waiting period before induction.
The Hall of Fame could change quite a bit before 2040, which would be just past its 100th anniversary. Can you wait that long before you see a Cubs favorite inducted? Because you're probably going to have to.