| $300 | Mar 28, 2025 | IUOE Local 399 Political Education Fund | — | — |
| $300 | Mar 25, 2024 | IUOE Local 399 Political Education Fund | — | — |
| $600 | Jul 28, 2023 | IUOE Local 399 Political Education Fund | Engineer | Chicago Park District |
| $200 | Mar 8, 2023 | IUOE Local 399 Political Education Fund | — | — |
| $600 | Jun 30, 2022 | IUOE Local 399 Political Education Fund | Engineer | Chicago Park District |
| $600 | Jun 30, 2022 | IUOE Local 399 Political Education Fund | Engineer | Chicago Park District |
| $200 | Feb 14, 2022 | IUOE Local 399 Political Education Fund | — | — |
| $5,800 | Oct 2, 2020 | Pat O'Brien for State's Attorney | Chairman CEO | Ryan Specialty Group |
| $5,800 | Oct 2, 2020 | Pat O'Brien for State's Attorney | Chairman CEO | Ryan Specialty Group |
| $200 | May 15, 2020 | IUOE Local 399 Political Education Fund | — | — |
| $300 | Sep 18, 2019 | IUOE Local 399 Political Education Fund | — | — |
| $25,000 | Nov 9, 2018 | Citizens For Erika Harold | Ceo | Ryan Specialty Group |
| $25,000 | Nov 9, 2018 | Citizens For Erika Harold | Ceo | Ryan Specialty Group |
| $100,000 | Nov 2, 2018 | Citizens For Erika Harold | Ceo | Ryan Specialty Group |
| $100,000 | Nov 2, 2018 | Citizens For Erika Harold | Ceo | Ryan Specialty Group |
| $250,000 | Oct 16, 2018 | Bill Daley For Mayor | CEO | Ryan Specialty Group |
| $250,000 | Oct 16, 2018 | Bill Daley For Mayor | CEO | Ryan Specialty Group |
| $250,000 | Oct 16, 2018 | Bill Daley For Mayor | CEO | Ryan Specialty Group |
| $250,000 | Oct 16, 2018 | Bill Daley For Mayor | CEO | Ryan Specialty Group |
| $150 | Aug 28, 2018 | IUOE Local 399 Political Education Fund | — | — |
| $150 | Aug 28, 2018 | IUOE Local 399 Political Education Fund | — | — |
| $250 | Aug 27, 2018 | IUOE Local 399 Political Education Fund | — | — |
| $250 | Aug 27, 2018 | IUOE Local 399 Political Education Fund | — | — |
| $100,000 | Aug 23, 2018 | Citizens For Erika Harold | Ceo | Ryan Specialty Group |
| $100,000 | Aug 23, 2018 | Citizens For Erika Harold | Ceo | Ryan Specialty Group |
| $200 | Jun 30, 2017 | IUOE Local 399 Political Education Fund | — | — |
| $200 | Jun 30, 2017 | IUOE Local 399 Political Education Fund | — | — |
| $200 | Jun 30, 2017 | IUOE Local 399 Political Education Fund | — | — |
| $200 | Jun 30, 2017 | IUOE Local 399 Political Education Fund | — | — |
| $5,000 | May 31, 2017 | Citizens for Bridget Gainer | Chairman & CEO | Ryan Speciality Group |
| $5,000 | May 31, 2017 | Citizens for Bridget Gainer | Chairman & CEO | Ryan Speciality Group |
| $50,000 | Nov 2, 2016 | Liberty Principles PAC | — | Ryan Enterprises |
| $50,000 | Nov 2, 2016 | Liberty Principles PAC | — | Ryan Enterprises |
| $50,000 | Nov 2, 2016 | Liberty Principles PAC | — | Ryan Enterprises |
| $50,000 | Nov 2, 2016 | Liberty Principles PAC | — | Ryan Enterprises |
| $50,000 | Nov 2, 2016 | Liberty Principles PAC | — | Ryan Enterprises |
| $240 | Aug 1, 2016 | IUOE Local 399 Political Education Fund | — | — |
| $240 | Aug 1, 2016 | IUOE Local 399 Political Education Fund | — | — |
| $240 | Aug 1, 2016 | IUOE Local 399 Political Education Fund | — | — |
| $100,000 | Nov 9, 2015 | Support Independent Maps | Chairman & CEO | Ryan Specialty Group |
| $100,000 | Nov 9, 2015 | Support Independent Maps | Chairman & CEO | Ryan Specialty Group |
| $150 | Sep 25, 2015 | IUOE Local 399 Political Education Fund | — | — |
| $100 | Aug 19, 2015 | IUOE Local 399 Political Education Fund | — | — |
| $25,000 | Jan 26, 2015 | Chicago for Rahm Emanuel | Executive | AON |
| $25,000 | Jan 26, 2015 | Chicago for Rahm Emanuel | Executive | AON |
| $25,000 | Jan 26, 2015 | Chicago for Rahm Emanuel | Executive | AON |
| $25,000 | Jan 26, 2015 | Chicago for Rahm Emanuel | Executive | AON |
| $5,300 | Dec 13, 2014 | Summers for Chicago | Chairman and CEO | Ryan Specialty Group |
| $5,300 | Dec 13, 2014 | Summers for Chicago | — | Ryan Signature Group |
| $150 | Aug 11, 2014 | IUOE Local 399 Political Education Fund | — | — |
| $200 | Jul 24, 2014 | IUOE Local 399 Political Education Fund | — | — |
| $200 | May 29, 2014 | 19th Ward Democratic Org | — | — |
| $200 | May 29, 2014 | 19th Ward Democratic Org | — | — |
| $50,000 | Apr 10, 2014 | Citizens for Rauner, Inc | Chairman | World Sport Chicago |
| $50,000 | Apr 10, 2014 | Citizens for Rauner, Inc | Chairman | World Sport Chicago |
| $50,000 | Apr 10, 2014 | Citizens for Rauner, Inc | Chairman | World Sport Chicago |
| $200 | Mar 17, 2014 | IUOE Local 399 Political Education Fund | — | — |
| $5,000 | Jan 17, 2014 | Citizens for Linda L Mastandrea | EXECUTIVE | RYAN SPECIALTY GROUP |
| $5,000 | Jan 17, 2014 | Citizens for Linda L Mastandrea | EXECUTIVE | RYAN SPECIALTY GROUP |
| $5,000 | Jan 17, 2014 | Citizens for Linda L Mastandrea | EXECUTIVE | RYAN SPECIALTY GROUP |
| $5,000 | Jan 17, 2014 | Citizens for Linda L Mastandrea | EXECUTIVE | RYAN SPECIALTY GROUP |
| $5,300 | Nov 21, 2013 | Citizens for Rauner, Inc | Chairman | World Sport Chicago |
| $5,300 | Nov 21, 2013 | Citizens for Rauner, Inc | Chairman | World Sport Chicago |
| $5,300 | Nov 21, 2013 | Citizens for Rauner, Inc | Chairman | World Sport Chicago |
| $5,300 | Nov 21, 2013 | Citizens for Rauner, Inc | Chairman | World Sport Chicago |
| $5,300 | Nov 21, 2013 | Citizens for Rauner, Inc | Chairman | World Sport Chicago |
| $2,500 | Oct 30, 2013 | Yes for Independent Maps | Chairman and CEO | Ryan Specialty Group |
| $2,500 | Oct 30, 2013 | Yes for Independent Maps | Chairman and CEO | Ryan Specialty Group |
| $2,500 | Oct 30, 2013 | Yes for Independent Maps | Chairman and CEO | Ryan Specialty Group |
| $200 | May 13, 2013 | 19th Ward Democratic Org | — | — |
| $200 | May 13, 2013 | 19th Ward Democratic Org | — | — |
| $450 | Jul 19, 2011 | Illinois Democratic Victory PAC | Retired | N/A |
| $450 | Jul 19, 2011 | Illinois Democratic Victory PAC | Retired | N/A |
| $100,000 | Dec 29, 2010 | Two Party System Inc PAC | Chairman | Ryan Specialty Group |
| $803 | Dec 27, 2010 | Two Party System Inc PAC | Chairman | Ryan Specialty Group |
| $125,000 | Nov 3, 2010 | Two Party System Inc PAC | Chairman | Ryan Specialty Group |
| $100,000 | Sep 30, 2010 | Two Party System Inc PAC | Chairman | Ryan Specialty Group |
| $100,000 | Sep 30, 2010 | Two Party System Inc PAC | Chairman | Ryan Specialty Group |
| $500 | Aug 24, 2010 | IUOE Local 399 Political Education Fund | — | — |
| $500 | Aug 24, 2010 | IUOE Local 399 Political Education Fund | — | — |
| $500 | Aug 24, 2010 | IUOE Local 399 Political Education Fund | — | — |
| $1,500 | Nov 17, 2009 | Friends of Edward M Burke | Executive | AON Corp |
| $1,500 | Sep 25, 2009 | 44th Ward Regular Democratic Org | Chairman | AON |
| $3,000 | Nov 19, 2008 | Friends of Edward M Burke | Executive | AON Corp |
| $360 | Jun 9, 2008 | Carpenters Local 13 PAC | — | — |
| $110 | Jun 24, 2005 | Carpenters Local 13 PAC | — | — |
| $110 | Jun 24, 2005 | Carpenters Local 13 PAC | — | — |
| $100 | Jun 14, 2005 | Carpenters Local 13 PAC | — | — |
| $100 | Jun 14, 2005 | Carpenters Local 13 PAC | — | — |
| $110 | Apr 11, 2005 | Carpenters Local 13 PAC | — | — |
| $110 | Apr 11, 2005 | Carpenters Local 13 PAC | — | — |
| $2,480 | Jul 2, 2003 | Carpenters Local 13 PAC | CARPENTER | MADE EFFORT |
| $1,140 | Jul 2, 2003 | Carpenters Local 13 PAC | CARPENTER | MADE EFFORT |
| $1,140 | Jul 2, 2003 | Carpenters Local 13 PAC | CARPENTER | MADE EFFORT |
| $2,480 | Jul 2, 2003 | Carpenters Local 13 PAC | CARPENTER | MADE EFFORT |
| $350 | Nov 21, 2002 | 27th Ward Regular Republican Organization | — | — |
| $1,000 | Mar 11, 2002 | Friends to Elect Roger G Fein | insurance | Ryan Enterprises Group |
| $1,000 | Mar 11, 2002 | Friends to Elect Roger G Fein | — | — |
| $250 | Feb 18, 2002 | Citizens for Maloney | — | — |
| $250 | Feb 18, 2002 | Citizens for Maloney | — | — |
| $500 | Apr 16, 2001 | Friends of Barack Obama | — | — |
| $500 | Apr 16, 2001 | Friends of Barack Obama | — | — |
| $1,500 | Dec 1, 2000 | Friends of Edward M Burke | Executive | AON Corp |
| $1,000 | Sep 19, 2000 | 42nd Ward Republican Organization | CEO | AON |
| $180 | Jun 16, 2000 | Carpenters Local 13 PAC | — | — |
| $325 | Nov 3, 1999 | 27th Ward Regular Republican Organization | — | — |