Whether it has been from fans, former players, or even members of the media, there has been no shortage of speculation over the years as to just how large a role Ted Phillips plays in the current state of the Chicago Bears. Now, following yet another tumultuous season at Halas Hall, you would have thought that something had to give, but no.

The Bears kept the status quo for the 2021 season.

After a whopping thirty-seven (37) years serving with the franchise, twenty-one (21) of which were spent as the Team President and CEO, the Bears need a change. There is plenty of history, fun, and shameful memories to go over here.

A Tenure Filled with a Handful of Amazing Moments and Spectacular Disasters

There’s no question that, since 1983, we’ve seen a real mix of awesomeness and dread at Halas Hall. Originally hired by the McCaskey family as the team’s controller on September 28th, 1983, he was present for the magical 1985 Super Bowl Shufflin’ Crew. He ascended through the ranks quickly with his promotion to the team’s Financial Director position in 1987. It was there he handled all contract negotiations for the players up until 1993.

In that very year of 1993, Ted was promoted again, this time to Vice President of Operations. He served in that role until February 10th, 1999. Ted was then named the new Team President and CEO of the Chicago Bears, replacing Michael McCaskey. Ted has remained in that role ever since.

Unfortunately, since 1999, we have seen plenty of mediocre-to-bad football on the field.

The overall win percentage since the 1999 season for the Bears has been around 0.51. In total, there have been six (6) playoff appearances, three (3) playoff victories, and one (1) Super Bowl Appearance (2006). Otherwise... there’s been a few strong seasons, some terrible seasons, and tons of mediocre seasons.

Highlights... and Lowlights

Photo by Jonathan Daniel/Getty Images

From 1987 to 2001, the Bears opted not to hire a true general manager. The last true GM for the Chicago Bears before that time was Jerry Vainisi, a forgotten name in history, and the person who replaced Jim Finks when Finks abruptly resigned in 1982. Jim Finks left in large part due to not having a say with the hiring of Mike Ditka. Jerry Vainisi was fired after the 1986 season.

The daily organizational responsibilities were then shared by Mike Ditka, Bill Tobin — the Director of Pro Personnel who was the De facto GM — and Michael McCaskey, with Ted Phillips handling negotiations. Once Mike Ditka and Bill Tobin were both shown the door in 1993, it was just Michael McCaskey and Ted Phillips. Dave Wannstedt was hired as Mike Ditka’s replacement on January 19th, 1993, and basically handled GM-level responsibilities as well.

Between 1993 and 1999, some of the franchise’s most notorious flops happened. Those blunders included the Rick Mirer trade, the Dave McGinnis coaching hire fiasco after Dave Wannstedt was fired, and the NFL Draft classes in between these years we’re less than stellar. Michael McCaskey decided to step away from the Team President role, naming Ted Phillips as his successor.

Two years later, following Ted Phillips’s latest promotion, it was deemed necessary to re-introduce the general manager position in Halas Hall. An external search firm was utilized in 2001, which ultimately led to the arrival of Jerry Angelo. The rest, as one would say, is history.

In all, Ted Phillips has hired three (3) different GMs and five (5) head coaches. Those GMs were Jerry Angelo (2001-11); Phil Emery (2012-14); and Ryan Pace (2015-TBD). The head coaches were Dick Jauron (1999-2003); Lovie Smith (2004-12); Marc Trestman (2013-14); John Fox (2015-17); and Matt Nagy (2018-Present).

Jerry Angelo and Lovie Smith had the most success of any GM/HC partnership. This included the Bears’ only three post-season victories, and lone Super Bowl appearance, since the 1980’s. We bared witness to Ridiculousness on special teams, a relentless defense featuring future hall of fame players, and a tough run game on offense that was quarterbacked by a bunch of guys trying to play quarterback. Oh, and Jay Cutler, too.

That is where the pleasantries will end. Once Jerry Angelo was canned in 2011, and then Lovie Smith in 2012, a rotating door began to spin wildly at Halas Hall. Phil Emery selected Marc Trestman over Bruce Arians in 2013, and the hire was signed off from above. The Marc Trestman Era will be considered the worst coaching hire in the Bears’ history for a multitude of issues.

Halas Hall was figuratively nuked in 2015, and in came Ryan Pace along with John Fox. Ryan Pace was recommended by Ernie Accorsi, who served as a 3rd party advisor for Ted Phillips and George McCaskey in their 3rd GM search. Following the announcement of Ryan Pace’s hire, the next HC search picked up. John Fox, coming off from a Super Bowl drubbing by the Seattle Seahawks, was hired shortly afterwards.

Once it became apparent John Fox wasn’t the best coach to develop a team around Ryan Pace’s QB in Mitchell Trubisky, John was terminated. Matt Nagy, the replacement for John Fox, has potential to last a while in Halas Hall, but time will tell.

So... Why Ted?

There has been a narrative by writers within the local community that Ted Phillips doesn’t need to be removed. Meanwhile, I have prime beach front property in Arizona I’d like to sell for what I’m sure is a reasonable rate. Or, would you prefer a week-long stay at my newest ski lodge resort in Florida?

Regardless of whether you’re scouting the players yourself, deciding which free agents to sign, or just hiring the people to do those jobs. You are what your team’s record says you are. In any business, football or otherwise, you own the success (and failures) of the team(s) you have assembled. It’s a part of being in organizational leadership.

He didn’t draft/sign the players; he just hired the people to draft/sign the players. He didn’t coach the players; he just hired the people to coach the players. He’s certainly not George Halas, the do-it-all owner, coach, and player who literally bled for his Chicago Bears. Ted just made the hiring decisions which have culminated into what we’ve seen for over two decades.

In the 2021 edition of the “End of Year” presser by the Chicago Bears, Chairman George McCaskey declared that Ted Phillips had no involvement in football operations. A blizzard happened in the panhandle of Florida when that statement was made.

Oh, actually, that’s a lie. It actually can snow in Florida.

By extension, Ted is at fault for what we’ve witnessed these past twenty-one seasons. He’s the guy who assembled the staffs to build and coach the roster. Therefore, he is involved in football operations. It’s just not acceptable. End of story.

When you have former players calling you out, most notably Olin Kreutz, it’s never a good sign. The issues have remained the same no matter who have been the GM or head coach. Inconsistent-to-bad QB play on offense, an occasionally good defense that lacks depth, and an inability to string together consecutive post-season appearances.

In order for the Bears to truly change, and I mean change, they must start from the top. Ted Phillips will always be respected in the building for his efforts these past twenty-one seasons. This includes his success in the re-design of Soldier Field, one that allegedly saved the McCaskey family more money than previously calculated. No one could ever question his commitment to the franchise. Just his judgment.

In a league that’s evolving in how teams are managed, Chicago’s atmosphere at the top of the organization has gone stale. Considering the spike in data analytics, modern fan engagement techniques, trends in roster management and contract negotiation strategies; the McCaskeys need someone who’s actively aware of these developments. A football person is needed for their chief football position, not an accountant.

Not to say Ted is a bad accountant, the Notre Dame and Northwestern Grad is well rehearsed when it comes to crunching numbers.

Alas, the point remains where a person who’s “in the know” and understands the modern game of football is truly what’s needed to get these Chicago Bears into the 21st century.

What (Should) Be Next?

This will depend entirely on what ownership would want to do with Ted’s position. Some teams have separated the powers into two different positions. Something like a Vice President of Football Operations with the other a Vice President of Financial Operations. This allows for each side to be separate, yet equal, and focus entirely on their fields of expertise.

If the Bears opt to go external with their hire, and split the positions up as previously mentioned, then I can think of at least one good name to consider:

Photo by Michael Hickey/Getty Images

Bill Polian would be an incredible hire who’d bring the expertise and vast amount of knowledge into their executive levels of leadership. Or, Chicago could opt to do what the Cleveland Browns did recently, and venture into the other major sport leagues for new perspectives. For example, plenty of noise has been made about Theo Epstein jumping into the NFL.

In the event Chicago decides to promote from within, there is one name to keep an eye on. Brian McCaskey (pictured under the heading), the current Vice President for the Chicago Bears. He brings in an Athletic Training background as opposed to Ted Phillips’s education in accounting. Brian is heavily involved with local programs, including the HearStrong campaign, and has been a personable representative of the Bears’ organization. If given the opportunity, I feel Brian would excel.

Regardless, the Chicago Bears need real change, from the top-down. Ted Phillips’s departure would be the first real step towards such change.