This town has no shortage of great sports leaders, but Axios Chicago’s tournament to crown the best was hardly a competition.
Driving the news: Hundreds of readers voted this week to name Phil Jackson as Chicago’s best coach of all time.
The intrigue: Jackson joins his 1996-98 Bulls in our ring of honor, as Axios Chicago readers already voted them the best local sports team of all time.
State of play: Jackson defeated many Chicago greats, from Ditka and Guillen to Maddon and Quenneville.
- Catch up on the tournament rounds below.
Championship
Phil Jackson vs. Joel Quenneville
The ultimate battle between the leaders of two United Center dynasties. It is basketball versus hockey for all the marbles.
Final Four matchups
Phil Jackson vs. George Halas
Jackson meets his first true test of this tournament, but his resume may give him the edge. Jackson’s body of work includes six NBA titles, but also two playoff appearances while Michael Jordan was away. As a matter of fact, Jackson never missed the playoffs during his Bulls’ tenure.
Halas is a Chicago legend, not just coaching but owning the Bears for decades. Halas has a 73-0 title game win to his credit, but it was in 1940. He doesn’t have a ton of contemporary success, but “Papa Bear” is the choice for generations of fans.
Joel Quenneville vs. Ozzie Guillen
Coach Q has defied the odds, knocking off Joe Maddon to get to the Final 4. His three Stanley Cups and several playoff appearances seem to outweigh his role in the ‘Hawks scandal. It’s hard to argue with what he got from his players on the ice, but it’s surprising that Chicago fans aren’t holding his off-the-ice behavior against him.
Ozzie holds a special place in Chicago fans hearts for the 2005 Sox improbable run to win the World Series. It was a special, dominant run. Since Guillen, the Sox have been somewhat rudderless, which is why you hear Ozzie’s name come up whenever there is a coaching vacancy. He’s also the only one of the final four that has transitioned to broadcast.
Elite Eight matchups
Phil Jackson vs. Ray Meyer
Jackson almost had a unanimous first round, which would have been a first in our Axios Chicago history of doing brackets. The Zen Master not only has six Chicago championships to his name, but he also has three more from his time in L.A. He also had Michael Jordan, Scottie Pippen, Kobe Bryant and Shaquille O’Neal.
Meyer is considered the best college coach in the city’s history. But even with those great teams in the late 70s, he couldn’t snag the championship trophy.
Mike Ditka vs. George Halas
This is the toughest matchup in the tournament so far. Halas won six NFL championships in his time. He’s one of the founders of the NFL! He hired Ditka! But Halas also faltered late in his career when the league expanded and never regained greatness after coaching the 1963 championship squad.
Ditka is “Da Coach,” and he led one of the most dominant teams in NFL history. He didn’t just coach winners, he coached winners with pizzazz. His schtick got tiring toward the end, but the Bears have yet to reclaim the glory he brought when he roamed the Soldier Field sidelines.
Joel Quenneville vs. Joe Maddon
Both of these coaches made it fun to root for Chicago sports teams in the 2010s. Coach Q won three Stanley Cups and brought a dynasty to the West Side. Later, he was accused of covering up a sexual assault and is currently banned from the NHL.
Maddon instantly became a fan favorite when he was chosen to lead the Cubs in 2015. He was colorful and eccentric and, oh yeah, he brought a World Series championship to Wrigleyville. He never won again, but the Cubs were perennial playoff contenders under his management.
Ozzie Guillen vs. Tony La Russa
Guillen is definitely on the Mount Rushmore of Chicago sports coaches. He brought a World Series to the South Side. Nobody else since 1959 can claim that feat.
La Russa almost got the Sox there in 1983, but he famously moved on and managed other teams, like the A’s and the Cardinals. La Russa came back in 2021, but don’t hold that against him.
First-round matchups
Phil Jackson vs. Lou Henson
Phil Jackson is our No. 1 seed, because his Bulls teams won six championships. All six happened to come when Michael Jordan was on the court. But there is no denying the impact the “Zen Master” has had on Chicago sports.
Lou Henson led the Fighting Illini men’s basketball team to several big wins and one heartbreaking Final Four loss.
Ray Meyer vs. Lovie Smith
Ray Meyer and his family ran DePaul men’s basketball for about 50 years! Ray led the Blue Demons to a couple of Final Four appearances and a slew of tournament appearances. He retired in 1984.
Lovie Smith brought winning back to the Bears organization during his tenure, which included the only Super Bowl appearance outside the ’85 Bears.
- He coached nine seasons and won over 80 games.
Mike Ditka vs. Tom Thibodeau
Mike Ditka is a tough out. The Bears coach not only led one of the most dominant teams to ever play in the NFL, but he was so entertaining while doing so.
- His press conferences are legend and his antics are notorious. The Bears haven’t been the same since he was fired in 1993.
Thibs turned around a perennial loser and made the Bulls a title contender. A lot of that had to do with Derrick Rose, but even when Rose got injured, Thibs kept his teams competitive.
George Halas vs. Don Zimmer
Papa Bear Halas will be tough to beat in this tournament. He’s one of the founders of the NFL! He coached the Bears to six championships, but he didn’t adjust well to contemporary football.
- One of the last moves he made as the Bears owner before he died? Hiring Mike Ditka.
Don Zimmer led the Cubs both as a third base coach in 1984 and manager in 1989. He is one of the most beloved figures in Cubs history but found even more success after moving to the Yankees organization.
Joel Quenneville vs. Gary Barnett
If this was two years ago, coach Q would be a shoo-in for a championship run. He led the ‘Hawks to three Stanley Cups and helped create a dynasty.
He also is currently out of the league for his role in covering up sexual assault allegations, causing a huge stain on his legacy.
Gary Barnett is the lone Northwestern Wildcat entry into the Sweet 16.
- In 1995, he led the ‘Cats to one of the most storied seasons in franchise history.
Joe Maddon vs. James Wade
Joe Maddon reversed the curse and led the Cubs to a World Series win in 2016. He will forever be the North Siders’ favorite manager.
- He also brought that Ditka-like eccentricity, holding fun press conferences and even opening a petting zoo during spring training.
James Wade was both the coach and the GM for the Chicago Sky when they won their championship in 2021.
Tony La Russa vs. Mike Keenan
La Russa is Chicago royalty, even though he came close to reversing that during his ill-fated return to the Sox.
- But he will be remembered for managing the 1983 squad that probably would have done better if not for the 1980s playoff format.
Mike Keenan brought the ‘Hawks close to glory in 1992 by returning to the Stanley Cup Finals. But he lost to the Pittsburgh Penguins.
Ozzie Guillen vs. Doug Bruno
Ozzie also fits into the Ditka category for his boisterous and eccentric behavior at press conferences and in the clubhouse.
- But make no mistake, Sox fans love Ozzie for taking a ragtag team to a World Series win in 2005. Fans are still hoping the team brings him back.
Doug Bruno is one of the winningest coaches in women’s college basketball, bringing DePaul to 25 NCAA Tournament appearances.
Editor’s note: This story has been updated with the latest rounds.
