The '85 Bears or '96 Bulls? Ranking Chicago's modern championship teams*

Chicago's major pro sports teams have won 12 championships since the 1985 Bears ended a 21-year drought (*The NASL champion Sting won titles in 1981 and 1984 and the Sky won the WNBA title in 2021, but their impact just doesn't compare to the Bears, Bulls, Blackhawks, Sox and Cubs — apologies to their loyal and hearty fans).

Here how I would rank them — and the standards are totally subjective on this. I considered a mixture of regular season/postseason dominance):

1. 1985 Bears — Considered one of the best NFL teams of all time, if not the best. Went 15-1 in the regular season — they were 12-0 before losing to the Dolphins 38-24 on Monday Night Football in Miami. Second in the NFL in points scored (28.5), first in points allowed (12.4). Got better as the season went on — the Bears allowed 10 points or fewer in 12 of their final 14 games. Won 21-0, 24-0 and 46-10 in the playoffs.

2. 1996 Bulls — Re-loaded in Michael Jordan's first full season back after retiring to play baseball, with Dennis Rodman acquired from the Spurs, the Bulls parlayed a 41-3 start to a 72-10 record — the best record in NBA history at the time. Dominated the playoffs, winning 14 of the first 15 games in taking a 3-0 lead in the NBA Finals vs. the Supersonics before taking the foot off the gas. One of the best NBA teams of all time. 

3. 1997 Bulls — Overshadowed by the 1995-96 Bulls, this team had a nearly equally phenomenal season. Started 17-1 and 49-6 en route to a 69-13 record (had a chance to tie the 72-10 team with four games left but lost three of them). Went 15-4 in the playoffs. Beat the 61-win Heat 4-1 in the Eastern Conference Finals. Beat the 62-win Jazz 4-2 in the NBA Finals — with Jordan's 38-points in the "Flu Game" breaking a 2-2 tie in Utah.

4. 2016 Cubs — With the pressure of great expectations after going 97-65 and reaching the NLCS in 2015, the 2016 Cubs started 25-6 and went virtually wire-to-wire with only one harmless mid-season bump to finish 103-58 and win the NL Central by 17 1/2 games. Went 3-0 in clinching games in the postseason, overcoming a 3-1 deficit in the World Series to break a 108-year championship drought.

5. 2013 Blackhawks — Coming out of a lockout, the Hawks got off to the best start in NHL history (21-0-3) and dominated the regular season, finishing 36-7-5 — the best points percentage (.802) in the NHL since 1977-78. Typically resilient in the postseason — overcoming a 3-1 deficit vs. the Red Wings in the second round and scoring twice in 17 seconds to beat the Bruins 3-2 in Game 6 to win the Cup.

   
   

6. 2005 White Sox — With a patchwork roster expertly put together by general manager Kenny Williams (only Joe Crede and Aaron Rowand came up through the Sox farms system among key position players), the Sox were a one-hit wonder but had all the qualities of a championship team. Without an established closer, they went an MLB-best 35-19 in one-run games. They were an MLB-best 52-39 on the road. And they went 11-1 in the playoffs, with 1 through 25 stepping up in big moments.

7. 1998 Bulls — The drama of the Last Dance — in the papers and backstage — and Scottie Pippen missing the first 35 games with an injury makes this final championship season an even bigger accomplishment. The Bulls started a pedestrian 8-7 without Pippen but figured it out and went 51-10 en route to a 62-20 record. Survived in Game 7 vs. the Pacers — the most precarious moment of the entire run — and beat the Jazz on the road to clinch title No. 6.

   
   

8. 1992 Bulls — Coming off their first NBA title, the Bulls and Michael Jordan took it up a notch in 1991-92, starting 37-5 on the way to a franchise-best 67-15 record (31-10 on the road). Stumbled in the playoffs a bit — tied 2-2 in their final three series and pushed to Game 7 vs. the Knicks in the second round. But facing Game 7 in the Finals vs. the Trailblazers, the Bulls' bench (Bobby Hansen, B.J. Armstrong, Stacey King, Scott Williams and Cliff Levingston) rallied from 15 down to win Game 6 and the second title.

9. 2010 Blackhawks — With the deepest roster of the Joel Quenneville-era teams — but with Jonathan Toews and Patrick Kane still only 21 — the Hawks met the challenge of championship expectations after having lost to the Red Wings in the Western Conference Final in 2009. Fast start (15-5-2) without Marian Hossa. Finished 52-22-8. Capped it off with a fabulous playoff run in which they went 8-3 on the road, with Kane's stealth OT goal in Philly giving the Hawks their first Cup since 1961.

An advertisement on the front page of an historic event was bad enough — a sign of the times. But "It's Ours" was an ill-conceived headline that made us look like homers. The Sun-Times — or Chicago, if that was the thinking — did not win the 2010 Stanley Cup.

10. 1991 Bulls — This team faced the challenge of dethroning the Pistons after losing to them in the conference finals the previous two seasons — but without the championship experience to lean on. Jordan & Co. took that step, going 61-21 in the regular season and 15-2 in the playoffs, including a memorable sweep of the Pistons in the conference finals. Game 4 of the Finals at the Forum — a 97-82 win — is an underrated moment.

11. 1993 Bulls — Facing the challenge of becoming the first team to win three consecutive NBA championships since the Celtics in 1959-66 the Bulls (57-25) were more vulnerable in 1992-93, but finished strong and turned it up in the playoffs (15-4). They won without home-court advantage against the Knicks in the Eastern Conference Finals (4-2) and the 62-win Suns in the NBA Finals (4-2) — avoiding Game 7 on the road in both series.

The Sun-Times had the Bulls on the back page of the first two NBA titles, but an ad on No. 3 — another sign of the times.

12. 2015 Blackhawks — The Hawks' slip seemed to be showing — third in the division, and then losing Patrick Kane — the NHL's leading scorer — to a potential season-ending fractured shoulder on Feb. 24. But Kane returned in time for the playoffs and the Hawks — pretty clearly on fumes — relied on their trademark resilience to overcome series deficits to beat the Ducks in seven games and Lightning in six for their third Stanley Cup.