Leading by Example: Littmann and O'Shea Have Meaningful Conversation Over Lunch at Chick and Ruth's

In a refreshing display of goodwill Mayor-Elect Jarred Littmann recently met with his former opponent, Bob O’Shea, for lunch at the city’s iconic Chick & Ruth’s Delly. The meeting, which took place shortly after the election, allowed the two leaders to connect across the aisle, demonstrating mutual respect and a shared commitment to the community.

During their discussion, Mayor-Elect Littmann expressed his appreciation for O’Shea’s passionate and respectful campaign. They explored Littmann’s vision and plans for leading Annapolis forward, underscoring their shared commitment to prioritizing the city’s interests above political differences.

The meeting between Littman and O'Shea demonstrate that leadership is not solely about winning, but rather about bringing people together for the city’s benefit.

Chick & Ruth’s owner, Spencer Jones, joined the lunch, adding a local flavor to the conversation. Littmann reportedly enjoyed the crab and cheese omelet—a menu item that may soon bear his name.

"Great Afternoon with Jared and Spencer. Getting together is how things get done," O'Shea said.

This meeting sets a tone of unity and collaboration as Annapolis prepares for its next chapter, showcasing both Littmann and O’Shea’s leadership approach, which emphasizes listening, learning, and leading by example.

Littmann and all eight City Council members will be sworn into office at 2:30 p.m. on Monday, Dec. 1, 2025 at Navy-Marine Corps Memorial Stadium. The event is free and open to the public. 

The first meeting of newly-elected Annapolis City Council will take place at 7 p.m. on Monday, December 8 in City Council Chambers (Annapolis City Hall, 160 Duke of Gloucester, Annapolis). At the first meeting of the new council, Mayor Littmann will appoint council members to standing committees.