Top 10 Fumbles of the Ted Phillips Era

Image by Zachary Rosenbaum –

Ted Phillips. The name brings a shudder to Bears fans. Since his rise to president and CEO in 1999, we’ve witnessed countless blunders that can only be described as a comedy of errors. With wind that the McCaskeys might be selling in the near future, we can only hope that a more competent president will follow suit (then again, the bar has not been set very high here… but I digress). But before we get too lost in thoughts of a shiny new president swooping in Theo Epstein-style and making the last 22 years a distant (albeit painful) memory, let’s remember to stay humble and honor our past. Whether having a direct hand in these gaffes or notoriously sitting back and not stepping in, Mr. Ted Phillips is in large part to thank for this incredible, and at times unbelievable, top 10 list.          

10. Hiring Dick Jauron over Bill Belichick

     Technically Jauron was named head coach in January of 1999 and Phillips was named president in February of 1999, but let’s not split hairs here. According to a long-lost Chicago Tribune article, Belichick (who was the defensive coordinator for the Jets at the time) was one of the finalists the Bears considered when interviewing for a new head coach. Jauron went on to finish a 35-45 record over five seasons with the Bears, and I think we all know how Belichick’s destiny turned out. There’s no way to know if Belichick would have had the same success in Chicago, and one can argue that Brady was the real catalyst for all those New England championships, but the fact remains: Phillips couldn’t help pick a good head coach if his job depended on it (wait, shouldn’t it?!).

9. Vetoing LaDainian Tomlinson Trade

     This one stings. According to John Mullin of CSN Chicago, Bears personnel sought a trade to land the future hall-of-famer during the 2001 draft, and Phillips vetoed it (why, Ted, whyyyyy??). There’s not much more to say here other than pointing out that we ended up using our first round draft pick that year on David Terrell (uhhh who?). Exactly.

8. Trading for Nick Foles

     $50M worth of cap space over three years is a whole lotta dough to shell out (on top of a compensatory fourth round draft pick!) for some insurance juuuust in case Trubisky didn’t pan out (spoiler alert: he didn’t, shocking!). We’re still on the hook for this horrible trade, and we didn’t even plan on starting Foles when Phillips either agreed to it or just sat back and let it happen. So we now have an injury-ridden, third string quarterback doing next to nothing while eating up a sizable chunk of guaranteed money (even with a restructured contract) and providing little incentive for other teams to offer up anything decent to trade for him. Classic.

7. Signing Mike Glennon

     We paid Glennon $18.5M to start 4 games total (of which he won one) and then took a $4.5M dead cap hit when we released him. It’s blatantly obvious that Phillips doesn’t possess the football acumen that should be inherent in an NFL team president, but with his background in accounting isn’t he supposed to be the “money guy”? Reports say other teams were willing to pursue Glennon in the $8M – $10M range. Now, I’m no financial expert, but paying an extra $10M when there wasn’t even any competition seems just a tad frivolous, no?   

6. Trading Greg Olsen

     In 2011 we traded Greg Olsen to the Carolina Panthers for a third round draft pick (a third round draft pick, that’s it!). Not only did we lose a smart and reliable offensive weapon, we also did it for unbelievably low value. All because Mike Martz (the offensive coordinator at the time) apparently didn’t want to fit him into his offensive scheme, even though Olsen was clearly one of Jay Cutler’s favorite targets. We can go down the rabbit hole here of “what if’s” – this move eventually paved the way for the Bears to acquire Brandon Marshall down the road – but at the time and at face value, this trade was just a horrible decision, plain and simple, and Phillips signed off on it.

5. Trading Thomas Jones

     Jones rushed for over 1,000 yards in consecutive seasons, and then in 2007, we abruptly traded him to the Jets in order to feature Cedric Benson in our backfield. It all stemmed from Jones requesting that the Bears restructure his contract, which was arguably warranted since he outplayed his deal, but clearly the request fell on the deaf ears of the front office. Urlacher, after retiring, pointed to this trade as to why the team seemed to fall apart after the spectacular 2006 Super Bowl run, stating that Jones was not only their best offensive player, but also a leader on the team. So, to recap, we traded our star running back because he made a reasonable request and then squandered the draft picks we ultimately got in exchange (Dan Bazuin, anyone??). Sounds about right for Phillips. 

4. Hiring Marc Trestman over Bruce Arians

     “Let’s do something completely out of left field and hire this unknown who had a bit of success in Canada over the guy who unexpectedly stepped up to lead the Colts to an 11-5 record and won NFL coach of the year in 2012.” Yeah, let’s not, Ted Phillips. With a 13-19 record before he got fired, I have to assume that Trestman gave the interview of his life to land that position, because any other logical explanation completely eludes me. Was the water at Halas Hall laced with drugs in early 2013? This was a head scratcher when it happened, and it’s an even bigger one in hindsight. 

3. Snubbing Urlacher

     Urlacher will forever be remembered as one of the most elite linebackers that Chicago has ever witnessed, and his career was unceremoniously brought to a close thanks to a cold and callous ultimatum. According to Urlacher, Phil Emery told him that the contract offer for the upcoming season would not change and that a decision needed to be made by that evening. Urlacher later learned of his release all thanks to a tweet. The fault for this one can be shared by many people – the McCaskeys and Emery being front and center – but the front office as a whole should be ashamed that his release didn’t even warrant a call from somebody. Still shaking my head over this one.      

2. Hiring Phil Emery

     Disastrous. Painful. Bewildering. I don’t think there are enough adjectives in the English language to properly describe the tragic tenure that was Phil Emery as general manager. His complete ineptitude to put together any semblance of a decent draft left holes in our roster that haunted the team for years, and his total lack of insight into the respectful way to treat players and personnel solidifies him as the worst GM in Bears history. I don’t think it’s hyperbole to say that Emery left the team in ruins, and Ted Phillips is the one to thank for hiring him.

1. Refusing to end his reign of terror

     This falls just as heavily on the McCaskeys’ shoulders as it does Phillips’. I don’t know why this man has been given over 20 years of chances to get it right, but he’s proven that by all metrics – from hiring ineffective general managers and coaches to blundering trades and drafts alike – he is mediocre at best. The Bears record during his tenure? 171-181. That’s a winning percentage of .485. If he is as devoted to this organization as he says he is, then he should have admitted his failures and resigned over a decade ago. Please, Ted, for the love of all that is good and holy, just give it up already! Haven’t we Bears fans suffered enough?!

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