| Pamela Rakestraw | $1,000 | Oct 22, 2016 | Friends for Susana Mendoza | Business Owner |
| Pamela Rakestraw | $1,000 | Oct 22, 2016 | Friends for Susana Mendoza | Business Owner |
| Pamela Rakestraw | $1,000 | Oct 22, 2016 | Friends for Susana Mendoza | Business Owner |
| Pamela Rakestraw | $1,000 | Oct 22, 2016 | Friends for Susana Mendoza | Business Owner |
| Stanley Rakestraw | $3,000 | Sep 30, 2016 | Citizens for Leslie Munger | Owner |
| Stanley Rakestraw | $3,000 | Sep 30, 2016 | Citizens for Leslie Munger | Owner |
| Pamela Rakestraw | $1,500 | May 16, 2013 | Preckwinkle for President | Co-Founder |
| Pamela Rakestraw | $1,500 | Sep 4, 2012 | Preckwinkle for President | Co-Founder |
| Stanley Rakestraw | $1,000 | Jan 27, 2010 | Friends of Todd H Stroger | COO |
| Stanley Rakestraw | $1,000 | Jan 25, 2010 | Friends of Todd H Stroger | COO |
| Stanley Rakestraw | $1,000 | Jan 25, 2010 | Friends of Todd H Stroger | COO |
| Stanley Rakestraw | $1,500 | May 15, 2008 | Friends of Todd H Stroger | COO |
| Stanley Rakestraw | $1,500 | May 15, 2008 | Friends of Todd H Stroger | COO |
| Stanley & Pam Rakestraw | $1,500 | Feb 15, 2002 | Citizens for Deborah Sims | — |
| Stanley & Pam Rakestraw | $1,500 | Feb 15, 2002 | Citizens for Deborah Sims | — |
| Stanley & Pam Rakestraw | $1,500 | Feb 15, 2002 | Citizens for Deborah Sims | — |
| Stanley & Pam Rakestraw | $1,500 | Feb 15, 2002 | Citizens for Deborah Sims | — |
| Pamela M. Rakestraw | $1,000 | Jul 31, 2001 | Friends of Bobby Rush | President |
| Stanley Rakestraw | $1,200 | Jul 20, 2000 | Friends of Bobbie L Steele | President |
| Stanley Rakestraw | $1,200 | Jul 20, 2000 | Friends of Bobbie L Steele | President |
| Stanley Rakestraw | $1,200 | Jul 20, 2000 | Friends of Bobbie L Steele | President |
“the ward with no alderman”