Teams owned: Chicago White Sox (1981-present), Chicago Bulls (1985-present)
Record as owner of teams: Chicago White Sox (2,978-2,946, ,502 winning percentage), Chicago Bulls (1,483-1,210, .550)
Championships won as owner: 7 (6 with Chicago Bulls — 1991, 1992, 1993, 1996, 1997, 1998; 1 with Chicago White Sox — 2005)
Bottom line: Jerry Reinsdorf bought the White Sox and Bulls for a combined $35 million. Today, the value of two franchises is estimated at $4.4 billion, according to Forbes Magazine. This is very good.
To this day, his treatment of Michael Jordan prevents Bulls from signing high-profile free agents. This is very bad.