Aromatic amines are a class of carcinogenic compounds present in tobacco smoke that are listed on the U.S. Food and Drug Administration (FDA) list of harmful and potentially harmful constituents (HPHCs) in tobacco products and tobacco smoke. The yields of six aromatic amines (1-aminonaphthalene [1-AN], 2-aminonaphthalene [2-AN], 3-aminobiphenyl [3-ABP], 4-aminobiphenyl [4-ABP], ortho-toluidine [o-TOL], and o-anisidine [o-ANI]) in the mainstream smoke from 23 commercial filtered cigars, 16 cigarillos, and 11 large cigars were determined using solid-phase microextraction coupled to gas chromatography triple quadrupole mass spectrometry (SPME headspace GC-MS/MS). The commercial cigars were smoked under the Cooperation Centre for Scientific Research Relative to Tobacco (CORESTA) Recommended Method 64 using a linear cigar smoking machine. The aromatic amine yields in the mainstream smoke from 50 commercial cigars show high levels of variation within and between the products. The average yields of the aromatic amines in the filtered cigars, cigarillos, and large cigars were 108, 371, and 623 ng/cigar for o-TOL; 6, 14, and 22 ng/cigar for o-ANI; 65, 114, and 174 ng/cigar for 1-AN; 25, 59, and 87 ng/cigar for 2-AN; 6, 17, and 27 ng/cigar for 3- ABP; and 8, 11, and 17 ng/cigar for 4-ABP, respectively. The relationships between aromatic amines and (1) total particulate matter (TPM), (2) water-soluble proteins, and (3) water-insoluble proteins were evaluated. We found that the aromatic amines showed a good linear response with TPM on a per cigar basis and showed significant positive correlations with proteins. In addition, the water-insoluble proteins make a greater contribution to the formation of aromatic amines compared to the water-soluble proteins.