This post was inspired by a comment made in Monday night's game thread. While no Cubs in living memory have World Series rings as members of the Cubs, the Cubs have acquired numerous players over the years who have celebrated World Series titles with other teams.
So I looked back to see which Cubs team had the most such players. You probably won't be surprised when you find out which club it was, but let me first explain how I went about this.
I went back only to 1984. Why? Well, mostly because this was pretty time-consuming and I thought nearly 30 years of it would make a representative sample; also, I figure these players are ones you're more familiar with.
Two more ground rules before you tell me in the comments that I missed someone: first, for a specific year, the player had to have the ring before he played for the Cubs. Thus, Greg Maddux is listed with the 2004, 2005 and 2006 teams, but not for the earlier Cubs teams he played on, since he won his ring in 1995. Second, although certain September callups and other players who didn't play in the postseason for teams that won World Series likely were given rings by their teams, I decided not to include players who I felt didn't make a significant contribution to that team. Thus Bob Dernier, who was a September callup for the 1980 Phillies and who played in 10 games as either a defensive replacement or pinch-runner, but who was not on their postseason roster, isn't included; some players, like Jason Marquis, are included even if they didn't play in the postseason, if they were part of the team the whole year. (There are a few others like this, but you get the idea.)
Here are all the players with World Series rings on each Cubs team from 1984-2012, listed in reverse chronological order starting with 2012, and the year or years they won rings. One more note: the players listed didn't have to spend the entire year with the Cubs, just be in a Cub uniform sometime during that season.
2011: 1. Ramon Ortiz (2002 Angels)
2010: 1. Derrek Lee (2003 Marlins)
2009: 5. Lee, Aaron Miles (2006 Cardinals), So Taguchi (2006 Cardinals, 2008 Phillies), Chad Fox (2003 Marlins), Neal Cotts (2005 White Sox)
2008: 5. Lee, Fox, Cotts, Jim Edmonds (2006 Cardinals), Jason Marquis (2006 Cardinals)
2007: 4. Lee, Marquis, Cotts, Cliff Floyd (1997 Marlins)
2006: 5. Lee, Greg Maddux (1995 Braves), Juan Pierre (2003 Marlins), Todd Walker (2004 Red Sox), Tony Womack (2001 Diamondbacks)
2005: 5. Lee, Maddux, Walker, Fox, Todd Hollandsworth (2003 Marlins)
2004: 5. Lee, Maddux, Walker, Moises Alou (1997 Marlins), Kent Mercker (1995 Braves)
2003: 5. Alou, Womack, Damian Miller (2001 Diamondbacks), Mark Guthrie (1991 Twins), Antonio Alfonseca (1997 Marlins)
2002: 3. Alou, Alfonseca, Joe Girardi (1996-98-99 Yankees)
2001: 2. Girardi, Kevin Tapani (1991 Twins)
2000: 3. Girardi, Tapani, Jeff Reed (1990 Reds)
1999: 4. Tapani, Jeff Blauser (1995 Braves), Rick Aguilera (1986 Mets, 1991 Twins), Gary Gaetti (1987 Twins)
1998: 2. Tapani, Gaetti
1997: 1. Tapani
1995: 2. Randy Myers (1990 Reds; also was on 1986 Mets but did not play in postseason), Howard Johnson (1984 Tigers, 1986 Mets)
1994: 2. Myers, Willie Wilson (1985 Royals)
1993: 3. Myers, Wilson, Candy Maldonado (1992 Blue Jays)
1992: 1. Danny Jackson (1990 Reds)
1991: 1. Jackson
1988: 3. Manny Trillo (1980 Phillies), Jim Sundberg (1985 Royals), Goose Gossage (1978 Yankees)
1987: 4. Trillo, Sundberg, Keith Moreland (1980 Phillies), Dickie Noles (1980 Phillies)
1986: 5. Trillo, Moreland, Ron Cey (1981 Dodgers), Davey Lopes (1981 Dodgers), Dick Ruthven (1980 Phillies)
1985: 6. Cey, Lopes, Ruthven, Moreland, Larry Bowa (1980 Phillies), Richie Hebner (1971 Pirates)
1984: 9. Cey, Lopes, Ruthven, Moreland, Bowa, Hebner, Noles, Warren Brusstar (1980 Phillies), Jay Johnstone (1978 Yankees, 1981 Dodgers)
What can we learn from this list? Obviously, GM Dallas Green picked up a lot of his former Phillies (six from the championship team of 1980), some of whom helped the Cubs win in 1984. The late '80s and early '90s teams had almost no one with a ring -- yet the 1989 team, with no one that had one, won 93 games. In recent years, the Cubs have had players with World Series titles; the results have been inconsistent at best. The fact that Green acquired some of his winning players makes me think that Theo will do the same -- thus, the idea that Kevin Youkilis might be a target. While Youkilis is clearly on the downside of his career, I don't think he's done yet -- and the experience of winning a World Series title is something that he could help impart to younger players. Here's an article by Amy K. Nelson at Baseball Nation that talks about how Octavio Dotel and Gerald Laird brought their St. Louis World Series rings from 2011 to show off to their new Tigers teammates, trying to impart a message:
Dotel said he and Laird try and pump up their teammates in the clubhouse before games, telling them how emotional this time is, that it was just like this for them last season in St. Louis.
"We're trying to give them the same idea, the same feeling we had last year," Dotel said.
Maybe there's too much to that. Maybe this is just an interesting exercise. But someday, we hope the list of Cubs wearing World Series rings is quite a bit longer.