While the events themselves should be well attended as they are about two weeks apart and the Houston cigar community is large enough and social enough to support both events, the controversy is in the naming rights.
However, a filing does not guarantee a trademark will be granted as there are caveats that will be discovered during the trademark discovery process.
Those rules can be found in the Trademark Manual of Examining Procedure which you can see by clicking here, but I have provided the relevant text below:
In Section 201.02 under Constructive Use Priority it states:
Upon registration, filing affords the applicant nationwide priority over others, except: (1) parties who used the mark before the applicant’s filing date; (2) parties who filed in the USPTO before the applicant; or (3) parties who are entitled to an earlier priority filing date based on the filing of a foreign application under 15 U.S.C. §1126(d) or §1141g (seeTMEP §206.02)