| $2,500 | Sep 30, 2025 | Citizens for Reilly | Retired | Retired |
| $2,500 | Sep 30, 2025 | Citizens for Reilly | Retired | Retired |
| $1,000 | May 9, 2025 | 42nd Ward Democratic Org | Attorney | self employed |
| $1,000 | May 9, 2025 | 42nd Ward Democratic Org | Attorney | Self |
| $2,070 | Feb 29, 2024 | Citizens for Reilly | Attorney | Self |
| $2,070 | Feb 29, 2024 | Citizens for Reilly | Attorney | Self |
| $1,500 | Jun 20, 2023 | Citizens for Reilly | Attorney | Self Employed |
| $1,500 | Jun 20, 2023 | Citizens for Reilly | Attorney | Self Employed |
| $1,000 | Feb 18, 2020 | Citizens for Reilly | Attorney | Self Employed |
| $1,000 | Feb 18, 2020 | Citizens for Reilly | Attorney | Self Employed |
| $1,500 | Jun 21, 2019 | Citizens for Reilly | Attorney | Self Employed |
| $1,500 | Jun 21, 2019 | Citizens for Reilly | Attorney | Self Employed |
| $1,000 | Jan 22, 2019 | Citizens for Reilly | Attorney | Self Employed |
| $1,000 | Jan 22, 2019 | Citizens for Reilly | Attorney | Self Employed |
| $500 | Mar 10, 2018 | 42nd Ward Democratic Org | — | — |
| $1,000 | Jan 5, 2018 | Citizens for Reilly | Attorney | Self Employed |
| $1,000 | Jan 5, 2018 | Citizens for Reilly | Attorney | Self Employed |
| $1,000 | Jan 5, 2018 | Citizens for Reilly | Attorney | Self Employed |
| $1,500 | Dec 30, 2017 | Citizens for Reilly | Attorney | Self Employed |
| $1,500 | Dec 30, 2017 | Citizens for Reilly | Attorney | Self Employed |
| $1,000 | Sep 22, 2017 | Citizens for Reilly | Attorney | Roger J. Kiley Jr. P.C. |
| $1,000 | Sep 22, 2017 | Citizens for Reilly | Attorney | Roger J. Kiley Jr. P.C. |
| $250 | Jun 26, 2017 | Hagerty for Judge | — | — |
| $600 | Mar 31, 2017 | Citizens for Lisa Madigan | Attorney | Roger J. Kiley Jr. P.C. |
| $1,500 | May 31, 2016 | The Burnham Committee | retired | retired |
| $1,500 | May 31, 2016 | The Burnham Committee | — | — |
| $1,500 | Dec 31, 2015 | Chicago for Rahm Emanuel | Attorney | Roger J. Kiley Jr. P.C. |
| $1,500 | Dec 31, 2015 | Chicago for Rahm Emanuel | Attorney | Roger J. Kiley Jr. P.C. |
| $1,500 | Dec 9, 2015 | Citizens for Reilly | Attorney | Roger J. Kiley Jr. P.C. |
| $1,500 | Dec 9, 2015 | Citizens for Reilly | Attorney | Roger J. Kiley Jr. P.C. |
| $1,500 | Dec 1, 2015 | Friends of Edward M Burke | Attorney | Schefsky et al |
| $1,500 | Dec 1, 2015 | Friends of Edward M Burke | Attorney | Schefsky et al |
| $1,000 | Sep 30, 2015 | Citizens for Reilly | Attorney | Roger J. Kiley Jr. P.C. |
| $1,000 | Sep 30, 2015 | Citizens for Reilly | Attorney | Roger J. Kiley Jr. P.C. |
| $2,500 | Sep 16, 2015 | Citizens for Lisa Madigan | Attorney | Roger J. Kiley Jr. P.C. |
| $2,500 | Sep 16, 2015 | Citizens for Lisa Madigan | Attorney | Roger J. Kiley Jr. P.C. |
| $2,500 | Jun 30, 2015 | Citizens for Lisa Madigan | Attorney | Roger J. Kiley Jr. P.C. |
| $2,500 | Jun 30, 2015 | Citizens for Lisa Madigan | Attorney | Roger J. Kiley Jr. P.C. |
| $25,000 | Dec 29, 2014 | Chicago for Rahm Emanuel | Attorney | Roger J. Kiley Jr. P.C. |
| $25,000 | Dec 29, 2014 | Chicago for Rahm Emanuel | Attorney | Roger J. Kiley Jr. P.C. |
| $2,500 | Sep 30, 2014 | 42nd Ward Democratic Org | Attorney | Self |
| $2,500 | Sep 30, 2014 | 42nd Ward Democratic Org | Attorney | Self |
| $5,300 | Jul 28, 2014 | Citizens for Lisa Madigan | Attorney | Roger J. Kiley Jr. P.C. |
| $5,300 | Jul 28, 2014 | Citizens for Lisa Madigan | Attorney | Roger J. Kiley Jr. P.C. |
| $1,500 | Jun 18, 2014 | 42nd Ward Democratic Org | Attorney | Self |
| $1,500 | Jun 18, 2014 | 42nd Ward Democratic Org | Attorney | Self |
| $5,300 | May 16, 2014 | Chicago for Rahm Emanuel | Attorney | Roger J. Kiley Jr. P.C. |
| $5,300 | May 16, 2014 | Chicago for Rahm Emanuel | Attorney | Roger J. Kiley Jr. P.C. |
| $250 | Dec 23, 2013 | Citizens to Elect Pat Spratt | — | — |
| $1,500 | Dec 3, 2013 | Friends of Edward M Burke | Attorney | Schefsky et al |
| $1,500 | Dec 3, 2013 | Friends of Edward M Burke | Attorney | Schefsky et al |
| $1,500 | Apr 25, 2013 | Citizens for Reilly | Attorney | Self |
| $1,500 | Apr 25, 2013 | Citizens for Reilly | Attorney | Roger J. Kiley Jr. P.C. |
| $1,500 | Mar 28, 2013 | Citizens for Reilly | Attorney | Self |
| $1,500 | Mar 28, 2013 | Citizens for Reilly | Attorney | Self |
| $300 | Feb 18, 2013 | Citizens for Lisa Madigan | — | — |
| $1,500 | Sep 17, 2012 | Citizens for Reilly | Attorney | Self |
| $1,500 | Sep 17, 2012 | Citizens for Reilly | Attorney | Self |
| $5,000 | Jun 27, 2012 | Citizens for Lisa Madigan | Attorney | Roger J. Kiley Jr. P.C. |
| $5,000 | Jun 27, 2012 | Citizens for Lisa Madigan | Attorney | Roger J. Kiley Jr. P.C. |
| $1,500 | May 11, 2012 | Citizens for Reilly | Attorney | Self |
| $1,500 | May 11, 2012 | Citizens for Reilly | Attorney | Roger J. Kiley Jr. P.C. |
| $200 | Sep 30, 2011 | Theis for Supreme Court | — | — |
| $1,000 | Sep 19, 2011 | Citizens for Reilly | — | — |
| $1,000 | Sep 19, 2011 | Citizens for Reilly | Attorney | Roger J. Kiley Jr. P.C. |
| $1,500 | Apr 15, 2011 | Citizens for Reilly | Attorney | Roger J Kiley Jr P.C. |
| $1,500 | Apr 15, 2011 | Citizens for Reilly | Attorney | Roger J Kiley Jr P.C. |
| $10,000 | Mar 18, 2011 | The Chicago Committee | Attorney | Roger J. Kiley, Jr. PC |
| $10,000 | Mar 18, 2011 | The Chicago Committee | Attorney | Roger J. Kiley, Jr. PC |
| $10,000 | Mar 18, 2011 | The Chicago Committee | Attorney | Roger J. Kiley, Jr. PC |
| $10,000 | Mar 18, 2011 | The Chicago Committee | Attorney | Roger J. Kiley, Jr. PC |
| $5,000 | Feb 14, 2011 | Chicago for Rahm Emanuel | Attorney | Roger J. Kiley, Jr. PC |
| $5,000 | Feb 14, 2011 | Chicago for Rahm Emanuel | Attorney | Roger J. Kiley, Jr. PC |
| $25,000 | Dec 27, 2010 | Chicago for Rahm Emanuel | Attorney | Roger J. Kiley, Jr. PC |
| $1,500 | Oct 12, 2010 | Citizens for Reilly | Attorney | Self |
| $1,500 | Oct 12, 2010 | Citizens for Reilly | Attorney | Self |
| $1,500 | Oct 12, 2010 | Citizens for Reilly | Attorney | Self |
| $1,000 | Oct 26, 2004 | Bill Lipinski's All-American Eagle | Attorney | Attorney |
| $1,000 | Oct 26, 2004 | Bill Lipinski's All-American Eagle | Attorney | Attorney |
| $1,000 | Oct 26, 2004 | Bill Lipinski's All-American Eagle | — | — |
| $1,500 | Jun 25, 2004 | The Burnham Committee | Attorney | Mayer Brown Platt |
| $500 | Aug 27, 2002 | Citizens for Dart | — | — |
| $500 | Aug 27, 2002 | Citizens for Dart | — | — |
| $1,500 | Nov 28, 2000 | 14th Ward Regular Democratic Org | Attorney | Mayer Brown & Platt |