With new ward, Velma Bailey eyes return to City Hall
In 1997, former 19th Ward alderman Velma Bailey was bounced from office amid a feud with then Mayor Freeman Bosley Jr.
Bailey was an outspoken critic of the mayor, who in turn backed a young Democrat– Mike McMillan, who had been an aide to Bosley– to run against her in the primary.
The battle was so intense that Bailey was actually issued a summons on Election Day for misdemeanor assault after a skirmish at the polls.
Fast forward eleven years, and Bailey is yet again gearing up for another pitched primary battle — and tangling with a man named Freeman Bosley.
This time, though, Bailey will by vying for a seat in the Third Ward, where the incumbent is the former mayor’s father, Freeman Bosley Sr.
Bailey still lives on Dodier Street, just like she did when she represented the 19th Ward.
However, when aldermen redrew ward boundaries after the 2000 census, Bailey’s home was written out of the 19th and dropped into the Third Ward.
Coincidence?
Either way, Bailey is hoping to get back to City Hall by unseating the older Bosley, who was first elected over three decades ago.
Bosley may be vulnerable — his narrow win in 2005 proved that — but the solid showing of his candidates in this summer’s committee races suggest he’s regained momentum.
If Bosley Sr. does need some tips for taking on Bailey, he’s got plenty of places to look — even if his son doesn’t have any of his old notes, McMillan, now the city’s License Collector, is easy to find at City Hall.



Mike McMillan was an outstanding alderman. Velma Bailey was a big mouth. Between Boz Sr. and Bailey, still have to give the edge to Boz … he’s a crank, but people respect him. Can’t say the same for Bailey.
I wonder if Bailey may have settled her scores with the Bosleys and is now entering the race as a stalking horse to split the anti-Bosley vote and thereby take votes away from the real threat to Bosley’s reelection, Jeffrey Hardin.