| $500 | Dec 19, 2024 | Friends of Timmy Knudsen | — | — |
| $1,500 | Dec 22, 2023 | Friends of Timmy Knudsen | CEO | McCaffery |
| $1,500 | Dec 22, 2023 | Friends of Timmy Knudsen | CEO | McCaffery |
| $5,000 | Nov 23, 2022 | Vote Yes for Clean Air, Clean Water, and | Chief Executive Officer | McCaffery Interests |
| $5,000 | Nov 23, 2022 | Vote Yes for Clean Air, Clean Water, and | Chief Executive Officer | McCaffery Interests |
| $10,000 | Dec 12, 2018 | Bill Daley For Mayor | NA | NA |
| $10,000 | Dec 12, 2018 | Bill Daley For Mayor | NA | NA |
| $10,000 | Dec 12, 2018 | Bill Daley For Mayor | NA | NA |
| $10,000 | Dec 12, 2018 | Bill Daley For Mayor | NA | NA |
| $9,297 | Aug 17, 2018 | Chicago for Rahm Emanuel | Real Estate Developer | Self-Employed |
| $3,655 | Aug 17, 2018 | Chicago for Rahm Emanuel | Real Estate Developer | Self-Employed |
| $9,297 | Aug 17, 2018 | Chicago for Rahm Emanuel | Real Estate Developer | Self-Employed |
| $3,655 | Aug 17, 2018 | Chicago for Rahm Emanuel | Real Estate Developer | Self-Employed |
| $35,000 | Jul 20, 2018 | Chicago for Rahm Emanuel | Real Estate Developer | Self-Employed |
| $35,000 | Jul 20, 2018 | Chicago for Rahm Emanuel | Real Estate Developer | Self-Employed |
| $500 | Oct 17, 2017 | Citizens for Bridget Gainer | CEO | McCaffery Interests |
| $500 | Sep 7, 2017 | Friends of Michele Smith | — | — |
| $1,200 | Mar 30, 2015 | Citizens to Re-elect John Pope for Committeeman | CEO | McCaffery Interests |
| $1,200 | Mar 30, 2015 | Citizens to Re-elect John Pope for Committeeman | CEO | McCaffery Interests |
| $10,000 | Mar 24, 2015 | Chicago for Rahm Emanuel | Real Estate Developer | Self-Employed |
| $10,000 | Mar 24, 2015 | Chicago for Rahm Emanuel | Real Estate Developer | Self-Employed |
| $10,000 | Mar 24, 2015 | Chicago for Rahm Emanuel | — | — |
| $10,000 | Mar 24, 2015 | Chicago for Rahm Emanuel | Real Estate Developer | Self-Employed |
| $250 | Feb 9, 2015 | Citizens for Bridget Gainer | — | — |
| $1,000 | Feb 4, 2015 | Citizens to Re-elect John Pope for Committeeman | CEO | McCaffery Interests, Inc. |
| $1,000 | Jan 30, 2015 | Friends of Natashia Holmes | Owner | McCaffery Interests |
| $1,000 | Jan 30, 2015 | Friends of Natashia Holmes | Owner | McCaffery Interests |
| $50,000 | Nov 24, 2014 | Chicago for Rahm Emanuel | Real Estate Developer | Self-Employed |
| $50,000 | Nov 24, 2014 | Chicago for Rahm Emanuel | Real Estate Developer | Self-Employed |
| $500 | Oct 7, 2014 | Hopkins for Chicago | — | — |
| $1,500 | Sep 26, 2014 | Friends of Alyx Pattison | Chairman & CEO | McCaffery Interests |
| $1,500 | Sep 26, 2014 | Friends of Alyx Pattison | Chairman & CEO | McCaffery Interests |
| $1,500 | Sep 26, 2014 | Friends of Alyx Pattison | Chairman & CEO | McCaffery Interests |
| $5,300 | Sep 9, 2014 | Chicago for Rahm Emanuel | Homemaker | None |
| $5,300 | Sep 9, 2014 | Chicago for Rahm Emanuel | Real Estate Developer | Self-Employed |
| $5,300 | Sep 9, 2014 | Chicago for Rahm Emanuel | Homemaker | None |
| $5,300 | Sep 9, 2014 | Chicago for Rahm Emanuel | Real Estate Developer | Self-Employed |
| $250 | Jul 30, 2013 | Friends of Bob Fioretti | CEO | McCaffery Interests |
| $250 | Jul 30, 2013 | Friends of Bob Fioretti | CEO | McCaffery Interests |
| $250 | Dec 7, 2012 | Friends of Bob Fioretti | CEO | McCaffery Interests |
| $500 | Jul 24, 2012 | 2nd Ward Democratic Org | — | — |
| $1,500 | Oct 28, 2011 | Leadership 2011 | CEO | McCaffery Interests |
| $1,500 | Oct 28, 2011 | Leadership 2011 | CEO | McCaffery Interests |
| $1,500 | Oct 28, 2011 | Leadership 2011 | CEO | McCaffery Interests |
| $1,500 | Oct 28, 2011 | Leadership 2011 | CEO | McCaffery Interests |
| $200 | Aug 11, 2011 | Friends of John Pope for Alderman | Owner | McCaffery Interests |
| $200 | Aug 11, 2011 | Friends of John Pope for Alderman | — | — |
| $200 | Jul 8, 2011 | Citizens to Elect Judge Lorna Propes | — | — |
| $1,000 | Apr 2, 2011 | Friends of Tim Egan | REAL ESTATE BROKER | SELF EMPLOYED |
| $1,000 | Apr 2, 2011 | Friends of Tim Egan | REAL ESTATE BROKER | SELF EMPLOYED |
| $1,000 | Apr 2, 2011 | Friends of Tim Egan | — | — |
| $1,000 | Dec 17, 2010 | Chicago for Rahm Emanuel | Real Estate Developer | Self-Employed |
| $6,702 | Oct 21, 2007 | Committee to Elect Anne M Burke | President | McCaffery Interests Inc. |
| $6,702 | Oct 21, 2007 | Committee to Elect Anne M Burke | President | McCaffery Interests Inc. |
| $1,000 | Jul 7, 2007 | Committee to Elect Anne M Burke | Consultant | McCaffery & Associates |
| $1,000 | Jul 7, 2007 | Committee to Elect Anne M Burke | Consultant | McCaffery & Associates |
| $5,000 | Jan 16, 2007 | Richard M Daley Campaign Comm | Management | Self Employed |
| $5,000 | Jan 16, 2007 | Richard M Daley Campaign Comm | Management | Self Employed |
| $2,000 | Aug 22, 2006 | Committee to Elect James A Deleo | McCaffery Interests | executive |
| $2,000 | Aug 22, 2006 | Committee to Elect James A Deleo | McCaffery Interests | executive |
| $2,000 | Aug 22, 2006 | Committee to Elect James A Deleo | McCaffery Interests | executive |
| $2,000 | Aug 22, 2006 | Committee to Elect James A Deleo | McCaffery Interests | executive |
| $1,500 | Dec 14, 2004 | Friends of Edward M Burke | Executive | McCaffery Interests |
| $1,500 | Dec 14, 2004 | Friends of Edward M Burke | Executive | McCaffery Interests |
| $500 | May 6, 2003 | Richard M Daley Campaign Comm | — | — |
| $500 | May 6, 2003 | Richard M Daley Campaign Comm | — | — |
| $1,500 | Jun 25, 2001 | Richard M Daley Campaign Comm | Housewife | — |