**Exhibit 31.1****CERTIFICATION**I, Kevin R. Callahan, Chairman of the Board and Chief Executive Officer of Affirmative InsuranceHoldings, Inc., certify that: 1. I have reviewed this quarterly report on Form 10-Q of Affirmative Insurance Holdings, Inc.;  2. Based on my knowledge, this report does not contain any untrue statement of a materialfact or omit to state a material fact necessary to make the statements made, in light ofthe circumstances under which such statements were made, not misleading with respect tothe period covered by this report;  3. Based on my knowledge, the financial statements, and other financial information includedin this report, fairly present in all material respects the financial condition, resultsof operations and cash flows of the registrant as of, and for, the periods presented inthis report;  4. The registrant’s other certifying officer(s) and I are responsible for establishing andmaintaining disclosure controls and procedures (as defined in Exchange Act Rules 13a-15(e)and 15d-15(e)) and internal control over financial reporting (as defined in Exchange ActRules 13a-15(f) and 15d-15(f)) for the registrant and have:(a) Designed such disclosure controls and procedures, or caused such disclosure controlsand procedures to be designed under our supervision, to ensure that material informationrelating to the registrant, including its consolidated subsidiaries, is made known to usby others within those entities, particularly during the period in which this report isbeing prepared;(b) Designed such internal control over financial reporting, or caused such internalcontrol over financial reporting to be designed under our supervision, to providereasonable assurance regarding the reliability of financial reporting and the preparationof financial statements for external purposes in accordance with generally acceptedaccounting principles;(c) Evaluated the effectiveness of the registrant’s disclosure controls and proceduresand presented in this report our conclusions about the effectiveness of the disclosurecontrols and procedures, as of the end of the period covered by this report based on suchevaluation; and(d) Disclosed in this report any change in the registrant’s internal control overfinancial reporting that occurred during the registrant’s most recent fiscal quarter (theregistrant’s fourth fiscal quarter in the case of an annual report) that has materiallyaffected, or is reasonably likely to materially affect, the registrant’s internal controlover financial reporting; and 5. The registrant’s other certifying officer(s) and I have disclosed,based on our most recent evaluation of internal control over financialreporting, to the registrant’s auditors and the audit committee of theregistrant’s board of directors (or persons performing the equivalentfunctions):(a) All significant deficiencies and material weaknesses in the design or operation ofinternal control over financial reporting which are reasonably likely to adversely affectthe registrant’s ability to record, process, summarize and report financial information;and(b) Any fraud, whether or not material, that involves management or other employees whohave a significant role in the registrant’s internal control over financial reporting.Date: August 9, 2007                                      /s/ Kevin R. Callahan   Kevin R. Callahan   Chairman of the Board and Chief Executive Officer