ESPN.comThe best and worst of Chicago's pro teams over the past 25 years:
Overall winning percentage: .504 (18th)
Best year: 1991
Predictably, all five of Chicago's pro teams have never had a winning season in the same year, mostly because the Cubs have had so few winning seasons. Two Chicago teams reached the championship in 1992 (Bulls won, Blackhawks lost). Best overall year was probably 1991 -- the Bulls won their first championship, the Blackhawks led the NHL with 106 points (although were upset in the playoffs), the Bears went 11-5 and made the playoffs, the White Sox were 87-75 and the Cubs ... well, the Cubs had a losing record.
Worst year: 1999
Ahh, a perfect season of ineptitude: 0 for 5. No Chicago teams made the playoffs as the Cubs went 67-95, the White Sox 75-86, the Bears 6-10, the Bulls 13-37 and the Blackhawks 29-41-12.
Best moment: The Bears' Super Bowl triumph in January of 1986 was almost inevitable -- but still glorious. Nonetheless, we give the nod to the Bulls' first NBA triumph in 1991. Michael Jordan and Co. had lost to the Pistons three straight years in the playoffs, including the previous two conference finals. So when the Bulls swept Detroit in the East finals and then beat the Lakers for the title, the new king was finally crowned.
Worst moment: What, besides the time Cubs manager Lee Elia blasted Cubs fans by saying, "They oughta go and get a (expletive) job and find out what it's like to go out and earn a (expletive) living. Eight-five percent of the (expletive) world is working. The other 15 percent come out here."
Durham. Bartman. Take your pick.
Best team: Let's make this easier. Vote in the poll to the right. The candidates:
Worst team: 2001 Bulls (15-67)
In three years under Tim Floyd in the post-MJ era, the Bulls went 13-37, 17-65 and 15-67. The 2001 edition was especially pathetic, even though it featured two future All-Stars in Elton Brand and Ron Artest. The Bulls finished last in the league in scoring (87.6 ppg) and were outscored by 9.1 points per game.
Best individual season: Michael Jordan, ???
With apologies to Sammy Sosa's 2001 (64 HRs, 160 RBI, 146 runs, .328 average) and a couple Frank Thomas MVP seasons, it boils down to MJ -- but which year? In 1987, he averaged 37.1 points per game. In 1989, he averaged 32.5 points, 8.0 rebounds and 8.0 assists -- but wasn't even named NBA MVP. In 1991, he averaged 31.5 points and won his first NBA title. He was amazing in 1993 (Charles Barkley won the MVP, however) and 1996, when he added the 3-point shot to his repetoire.
The vote here: 1991, when he also averaged 31.1 points and 8.4 assists per game in the playoffs and won his first title. But any year from 1987 to 1993 is certainly acceptable.