Years ago Kevin Ksen and I looked into creating a database of Worcester City Council votes; we learned that controversial measures are usually dealt with in committee, rather than by the full Council, so there are relatively few split votes.

Here are a few controversial votes from the past couple Councils that come to mind. Others?

• Pay Raise: December 19, 2006. Councilors' salary increases from $15,750 to $29,000. More background and aftermath in this article. Many said this vote would be important for the following election; it was not.
• Anti-Street Vendor Regs: September 9, 2008, "Amending Chapter Fourteen of the Revised Ordinances of 2008 relative to Street Vendors." More background.
• City Manager's Pools Plan: (In contrast with the various pools plans advocated by the hundreds of people who came to public meetings over several years to discuss this.) September 9, 2009, "Request City Manager implement an aquatics plan".

FWIW, I tend to think all these measures were unwise. Looking at this table, my opinion of the councilors is not much correlated with how they voted.