Amazon Route 53: Could It Be the Telltale Sign That Jeff Bezos Is Buying the Chicago Bears?

The hypothetical road that leads to understanding where the Chicago Bears will actually build a new stadium might involve a hint from the actual expressway that would be the predominant route used by motorists to travel to the new Chicago Bears stadium. The signs that lead to such understanding and awareness might be hidden in plain sight. Route 53.

Illinois Route 53 is a busy expressway that passes the western border of Arlington Heights and also passes adjacent the former Arlington Park property now owned by the Chicago Bears Football Club. In fact, the Chicago Bears Football Club owns a large billboard on the former Arlington Park property just east of Route 53 for display on Route 53. According to rumors and common sense awareness, an expressway interchange would be necessary to connect a new Chicago Bears stadium in Arlington Heights via a direct on-ramp and off-ramp to and from Illinois Route 53.

Amazon Route 53, since 2010, is a Domain Name System (DNS) service created for the highly successful Amazon Web Services (AWS) that routes end users to Internet applications. AWS began in-house at Amazon around 2000 to 2002, and became a cloud-based service offered publicly to other businesses by 2006. The public AWS grew tremendously, partly by harnessing the entrepreneurial spirit of companies (and new technology customers) that were using AWS.

When developed in 2010, the technical reference of the “Amazon Route 53” name referred to TCP or UDP port 53. Transmission Control Protocol (TCP) and the User Datagram Protocol (UDP) use one port for duplex, bidirectional traffic; and Port 53 is one of a list of TCP and UDP port numbers used in protocols for operation of network applications. The ‘route’ element in the name Route 53 is an inspiration from the iconic ‘Route 66’ in the USA, according to WHIZLABS (an online learning provider for various digital technologies). You can also think of the ‘route’ part as an indication of the path for routing traffic to Amazon DNS.

Amazon Web Services, Inc. (AWS) has become a highly successful subsidiary of Amazon that provides on-demand cloud computing platforms and APIs (Application Programming Interfaces) to individuals, companies, and governments, on a metered, pay-as-you-go basis. Companies that use AWS include Airbnb, ESPN, Facebook, Linkedin, Netflix, Pfizer, Nordstrom, X, and more. According to CLOUDZERO, there was an announcement that Twitter (now X) would use Amazon Web Services (AWS) to power its main timeline — just an example to give you an idea how important AWS is to business. According to The Information (a technology media website founded by journalist Jessica Lessin), the deal to power the X.com main timeline involved a five-and-a-half-year contract with AWS worth $510 million.

The Route 53 connection is strangely coincidental, considering the interest of Jeff Bezos in owning an NFL team, and rumors that he is involved in considering a purchase of the Chicago Bears.

If it is true that Amazon’s Jeff Bezos is buying the Chicago Bears, the question to ponder would be, “Is the Route 53 conceptual connection just some strange coincidence, or did Jeff Bezos have aspirations and foresight to anticipate that somehow and some way and someday, he would own the Chicago Bears and build a new NFL-class stadium at the former Arlington Park location next to Route 53?” The latter sounds strange, but not necessarily any stranger than the story of the vision of a man that founded an online bookstore company out of his garage in 1994 while the public’s use of the Internet was scarce and in its infancy; and eventually developed his business into one of the largest companies in the world that sells just about everything online to almost everyone in the world, while bringing shipping for Amazon in-house with Amazon’s own aircraft and electric trucks.

By design or by coincidence the combination of a Route 53 expressway that connects to an Amazon Bears football stadium would be marketing brilliance. Imagine Route 53 being named Amazon Route 53 — at least informally — and bringing people to an Amazon Chicago Bears NFL football stadium.

Other Loose Ends that Indicate Jeff Bezos is buying the Chicago Bears, or indicate logical conclusions that Jeff Bezos would be interested in buying the Chicago Bears

Daily Herald columnist Jim O’Donnell on May 26, 2021 [paywall] indicated that he learned from a source with “exceptional knowledge of the working dynamic within the McCaskey family” that “(t)here is some internal strife going on among family members to sell … now.”

IF THE SALE OF THE BEARS is announced in the weeks ahead, there are three suitors who loom larger than all others — Pat Ryan, Jeff Bezos and Neil Bluhm.

— Jim O’Donnell

According to O’Donnell in 2021, Pat Ryan in a partnership with Andy McKenna, owned 19.7% of the Chicago Bears, and held the right-of-first-refusal as “primary investor” if any of the McCaskey stock comes up for sale. Chicago businessman Andrew McKenna, a part owner of the Bears and member of the team’s board of directors, passed away Tuesday, February 7, 2023 at the age of 93. According to a Chicago Tribune staff report last updated August 11, 2021 (originally published December 27,1998), the report then indicated that “Patrick Ryan, president of Aon Corp., and Andrew McKenna, president of Schwarz Paper Co., own 19.7 percent of the Bears, the portion that once belonged to Mugs Halas. (Both McKenna and Ryan sit on the Tribune’s board of directors.) Ryan owns about 90 percent of the portion and is viewed by insiders and outsiders with a wary eye.” The Chicago Tribune staff report added, “The McCaskey family has right of first refusal on any sale of minority stock; the Ryan and McKenna block has second refusal.”

According to the Chicago Tribune staff report “Family Matters”, Ryan and McKenna became partners in 1990 to alleviate the financial burden the McCaskeys felt when the club chose to match a $17 million offer by JMB Realty for Mugs Halas’ stock held by daughter Christine and son Stephen. Mugs Halas (George Halas, Jr, former president of the Chicago Bears and son of Chicago Bears founder and NFL co-founder George Halas) died on December 16, 1979.

“Either we own the Bears or we are the rich McCaskeys. We are not the rich McCaskeys who own the Bears.”

— Virginia McCaskey recalling a quote she liked from someone in the McCaskey family (Chicago Tribune/sometime from around 1998 to 2021, unknown precisely)

“I don’t think we can go for very long without being in the playoffs and being in the race for the Super Bowl without losing more of this terrific reservoir of support. We have to show the fans we’re doing everything we possibly can to get back.”

— Former Chairman of the Chicago Bears, Michael McCaskey (Chicago Tribune 1998)

“A lot of things in any team’s situation that loom as big problems are solved by winning.”

— Former Chairman of the Chicago Bears, Ed McCaskey (Chicago Tribune 1998)

Ed McCaskey died April 8, 2003, and Michael McCaskey died May 16, 2020.

Then on November 18, 2021 Dave Williams of Barstool Chicago (whitsoxdave/x) posted, “I just received a call that Jeff Bezos is currently at Halas Hall (Chicago Bears headquarters). I don’t know wtf that means, why he’s there or if it’s even true but take that as you will”

The Chicago Bears is a flagship NFL team — one of only two. If you’re a billionaire, and you’re going to own an NFL team, the top two historical choices would be the Chicago Bears and the Arizona Cardinals. Both charter members of the NFL, the Decatur Staleys (now the Chicago Bears) and the Chicago Cardinals (now the Arizona Cardinals), are the only two original football teams to survive to the current day in the NFL.

MLFootball/X reported in early December 2024 that Amazon founder Jeff Bezos is the STRONG FAVORITE to BUY the Chicago Bears and be their next owner. MLFootball/X cited BovadaOfficial/X as the source. Bovada provides an online betting experiences in the categories of Sport, Casino, Poker and Horseracing.

Sports Illustrated acknowledged that Jeff Bezos is rumored to be the frontrunner to buy the Chicago Bears in an article by Tom Jensen speculating that San Francisco 49ers head coach Kyle Shanahan’s interest in a move to the Chicago Bears could go up if Bezos offered the right salary and would give Shanahan final personnel control. However, Jensen wrote that he doesn’t think the Shanahan scenario with the Chicago Bears would happen.

Jeff Bezos was rumored in 2021 to be interested in the Denver Broncos.

Also in 2021, Amazon acquired the exclusive rights to Thursday Night Football (TNF) beginning in the 2023 season under the NFL’s new broadcasting deals. The Amazon accomplishment marked the first time that the NFL had sold one of its main television packages to a digital media company — Amazon Prime.

Also, according to Martha Muir and Anna Nicolaou of the Financial Times [paywall], Bezos, who might not have been involved in the bidding first-hand, was outbid in an attempt to buy the Washington Commanders by an ownership group led by Josh Harris, who also owns the Philadelphia 76ers and the new Jersey Devils.

Ironically, the City of Chicago in 2017 had a plan to attract a Chicago Amazon HQ2 headquarters at the former Michael Reese Hospital site, which is now under consideration for a Chicago Bears stadium in the City of Chicago — secondary to the Soldier Field site.

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