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A Sample of Some Recent Real Estate Investments Among Former Bears' Coaches and Players

Updated: May 6, 2019

I recently read some of the latest real estate purchases in regarding former Bears' coaches and players. This piqued my interest, how well did these real estate transactions worked out for the majority of these ex-Bears? I know the NFL coaching space has a high turnover so the tenure of this position may only be just a few years before they are fired. Same situation applies to players, the average tenure of an NFL player is less than 4 years. A player may be traded to the Bears or drafted by them and decide to purchase a home in the Chicago, perhaps thinking their tenure will be a long one. This may or may not come to fruition. The sole deviation is Brian Urlacher, the former Bear and now part of the NFL Hall of Fame. He played all 13 seasons with the Bears, an anomaly for most NFL players.

Back to real estate investments. A small sample size, I chose 5 former Bears who either sold their house or are in the process of doing so. I was interested in how much they paid for their house, when it was purchased and then sold and the final selling price.

First to Glencoe

Former Chicago Bears head coach Marc Trestman and his wife, Cindy, sold their Glencoe townhome in December 2018 after nearly two years of listing the property. The three-bedroom, sold for $550,000.

He coached the Bears from 2013 - 14. The Trestman's purchased the home in April 2015 for $625,000. In less than 5 years, the house depreciated 12%. A wise decision by the Trestman's to not buy a multi-million dollar mansion a few years after the Great Recession. Some may say that his coaching success was no better than this real estate purchase.

Next is Lake Forest

John Fox, former Bears head coach sold his home for a $400,000 loss. After being hired by the Bears in 2015, a few months later, John Fox purchased the country-style estate for $3.275 million. This property sold in 2019 for $2.875 million, a $400,000 loss. In other words, it depreciated 8.2% in 4 years.

John coached to Bears for 3 seasons even though his contract was for 4. He won 14 games during that span and lost 34. His winning percentage at the helm of the Bears was 38%. I might conclude that this real estate purchase, even though it depreciated 8.2% over 4 years was marginally more successful than his Bears' tenure.

On To Highland Park

Former Carolina Panthers, Chicago Bears, and Green Bay Packers defensive end Julius Peppers purchased a home in 2010 for $1.8 million. He sold the property in March 2018 for $1,062,500, a loss of around $747,500.

Peppers had purchased it from former Chicago Bulls player B.J. Armstrong who purchased the property for $1.4 million in 1994. During Armstrong's ownership, the property appreciated around 29% which is respectable although he owned the property for 16 years so that means it appreciated less than 2% per year during that time. However, Peppers was not so fortunate, by having a loss of $747,500, it depreciated 53%. I sense Peppers did a much better job chasing down quarterbacks than this particular real estate investment example.

Mettawa Is Next

As of December of 2018, Brian Urlacher is attempting to sell his 9.4-acre estate for less than $2 million. The current asking price is $1 million lower than the original asking price. I'm unable to provide any information on how many times the asking price has been lowered to help entice prospective buyers to seriously consider this property. His Mettawa home was purchased in 2004 for $2.3 million.

According to, the listing agent for this property had told Crain's Chicago Business that Urlacher had invested $1 million into upgrades to the property over these 14 years. Unfortunately, he'll never be able to recoup the upgrades he made to this property. I wonder if he got good advice on whether upgrades to his property was a fiscally sound idea.

In summary, if he sells his property for $1.9 million, the loss is $400,000, or depreciation of 17%. And that's not even considering all the upgrades he's made to the property over the last 14 years. It's a no brainer than Hall of Famer Urlacher performed at an all-star level on the gridiron compared to a real estate investor.

And Lastly, Let's Not Forget about Winnetka

Former Chicago Bears linebacker Hunter Hillenmeyer and his wife Sharon sold their Winnetka home in sold it mid-summer of 2017 for $1.325 million. They purchased the home back in 2008 for $1.44 million.

If my math is correct, their loss was $115,000, an 8% depreciation amount. However, one needs to realize that they owned the home for nearly 10 years so it may not have been the best investment to make.

Overall, I was a little surprised on the lack of appreciation in their real estate investment. All of these purchases involved the Chicago North Shore besides Brian Urlacher's home currently on the market (Mettawa which is just west of Lake Forest). Don't know if this applies to large mansions and estates on the North Shore or if this phenomenon applies to smaller homes too where most homes over the last 5-10 years or so have not been good investments. Perhaps former Bears' coaches and players have received bad advice when they purchased their home. Or perhaps it shows how crazy the real estate market is, especially among more expensive homes in the Chicago area. Either way, I'll let the reader be the judge.

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