[1] He made his initial fortune in real estate, taking advantage of the Frank Lyon Co. v. United States decision by the United States Supreme Court, which allowed economic owners of realty to sell property and lease it back, while transferring the tax deduction for depreciation to the title owner.

[7][8] Reinsdorf was in the stands the day Jackie Robinson debuted for the Brooklyn Dodgers, "breaking the color barrier" as the first black player permitted by white ownership.

[8] Reinsdorf worked as an IRS lawyer after graduating from Northwestern in 1960, where his first case concerned the tax delinquency of Bill Veeck, who at the time owned the White Sox.

He sold his business interests in the real estate partnership in 1973 and formed Balcor, which raised US$650 million to invest in buildings under construction.

He sold Balcor in 1982 for $102 million to Shearson Lehman Brothers, the investment banking and brokerage arm of American Express.

[15] He followed previous eccentric White Sox owners Charles Comiskey, who was known as a miser, and Veeck, who was known as a prankster who gutted the team by trading away promising prospects.

[7] The Bulls drafted Horace Grant and Scottie Pippen and traded for Bill Cartwright to join John Paxson and Michael Jordan under the tutelage of head coach Doug Collins.

[29] Whereas before Reinsdorf's purchase the team had an average attendance of 6,365 in the 17,339-seat Chicago Stadium,[7] from November 20, 1987, through Jordan's 1998 retirement, the Bulls sold out every game,[23] including their first few seasons at the United Center, where they play to this very day.

[39][40] His 1996 signing of Albert Belle made news because of his widely publicized general opposition to spiraling player salaries.

[17] He complained about old Comiskey Park with its foibles such as numerous obstructed view seats and threatened to move the White Sox.

[7] Reinsdorf and Chicago Blackhawks owner William Wirtz contributed $175 million to fund the construction of the largest arena in the United States.

[56] In the 1980s, Reinsdorf, Bud Selig and the American League President colluded to dissuade the Philadelphia Phillies from signing Lance Parrish who was a Detroit Tigers free agent.

[59] Some fans and columnists have accused Reinsdorf of breaking up the championship Bulls team after their third straight title and sixth in eight years, claiming the Bulls could have competed for more titles with Michael Jordan, Scottie Pippen and good support from the rest of the team that in the eight-year span included Dennis Rodman, Horace Grant, Toni Kukoč, Ron Harper, B. J. Armstrong, and coach Phil Jackson.

[65] In August 2009, it was reported that Jerry Reinsdorf & Ice Edge LLC had dropped its bid for the Coyotes, leaving only Balsillie and the NHL as bidders for the team.

The overhaul included the removal of top rows of the upper deck, replacement of the baby blue seats with traditionally-colored green ones and dozens of other upgrades.

[71] Prior to the seven-year overhaul, the 2001 White Sox barely broke even financially with a $700,000 operating profit on revenues of $101.33 million.

[72] Reinsdorf won a major revenue sharing legal battle with other NBA owners over the Chicago Bulls broadcasts on WGN-TV.

The 55 game schedule on the superstation for an audience of 35 million competed with the NBA broadcasts, but Reinsdorf was permitted to maintain the contract.

[74] Reinsdorf will also be remembered as the owner of the 2024 White Sox, the team that broke the Major League Baseball single-season loss record, previously held by the 1962 New York Mets.

[75] It's alleged that he intentionally tanked the team in order to get them moved to Nashville, Tennessee, where he had secretly met with the mayor in the summer of 2023.

[10] The White Sox Charities have donated to the Chicago Park District with particular purpose of funding construction and maintenance baseball and softball fields.

[4] He has been a member of the board of directors of Shearson Lehman Brothers, Inc., the Northwestern University Law School Alumni Association, LaSalle Bank, EQ Office and numerous other corporations and charities.

Throughout the years, Reinsdorf has been active in the affairs of baseball, serving on the Executive Council and Ownership, Long Range Planning, Restructuring, Expansion, Equal Opportunity, Strategic Planning, Legislative and Labor Policy Committees of Major League Baseball, he also serves on the Boards of MLB Advanced Media and MLB Enterprises.

[4] In 2013, Reinsdorf partnered with Mark Sullivan, Noah Kroloff, Dennis Burke, David Aguilar, and John Kaites to found Global Security and Innovative Strategies.