Robert Bobb

City Administrator Slugger

Bob was supposed to be a professional baseball player. At least that was what his dad wanted him to be. As a teenager in southwestern Louisiana, he played third base on his dad’s sandlot team.His family would crowd around the radio, listening for the crack of a bat and a home run for their favorite team, the Brooklyn Dodgers.

Bob grew up in a deeply segregated setting on a sugar cane plantation. His father sowed, harvested and refined sugar cane. His mother was a domestic worker for a wealthy physician. The only integrated institution was the local Catholic Church, where the white priest and nuns welcomed Bob’s family every Sunday.

Education, his parents made clear, was the only way up. Bob’s father would sit down with him and his four siblings every night to check their homework. At the plantation’s one-room school, older grades would teach the grade just below.

Bob would be the first in his family to complete high school and the first to head off to college, at the HBCU Grambling State. The country was in the throes of the Civil Rights struggle, and he recalls passing by burning crosses on his way to campus. Although he did not lead student protests, he was sure to be a part of them.

Bob's first employer, a Connecticut-based insurance company, made it clear to Bob that he was an affirmative action hire. He arrived in 1968, his first trip outside of Louisiana, without a winter coat. All the other new recruits came from Ivies.  

An older colleague Mr. Simpson took Bob under his wing, bought him a coat, and coached him in the ways of corporate management. He invited Bob over for a fancy meal at his home. He walked Bob through how to set a table for formal entertaining. Bob chuckled to himself. He didn’t have the heart to tell Mr. Simpson he already knew; his mother taught him that part.

He worked his tail off in Hartford for two years to prove himself, and was one of the youngest in the headquarters to be promoted to administrative manager. The company sent him to Detroit to turn around a troubled branch office. He held monthly performance meetings and followed corporate procedures by-the-book. Within a year, the team was moving in lockstep.

From there, Bob left the world of insurance and entered municipal government, first managing public utilities in Kalamazoo, then serving as its assistant city manager and eventually city manager. He came to understand city operations and finances from every angle—including when disaster strikes.  

In May 1980, a tornado tore through downtown Kalamazoo. Bob immediately went out to the streets to help save lives. He understood how important it was to be a visible symbol of active city leadership.

For the next few decades, he jumped from city to city—Santa Ana, Richmond, Oakland, DC, New Orleans and Detroit—getting their administrative and budget affairs in order. He was the guy who could make sense out of chaos, find the reins, pull them in, and kickstart government services back into gear.  

Mayor Tony Williams asked Bob to serve as DC City Administrator in some of the District’s darkest days of financial and service collapse. He was also President of the DC State Board of Education for three years.  

Restructuring New Orlean’s finances after Katrina was one of the highlights of his career. He was born there and in his earliest years lived in one of the low-income wards. The public employees blew him away. Many had stayed to man the pumps as flood waters rose. And when their families left for Houston or Baton Rouge, they stayed to put the city back together.  

Now he runs his own “how to turn things around” consulting practice. He’s an expert witness on Chapter 9 bankruptcy. He’s helped the Moroccan and Puerto Rican governments straighten out their finances and provided oversight for Azerbaijani elections.

For someone so often thrown into a thicket of other people’s problems, his sunny can-do disposition has served him well. So has his strength and professionalism. Bob is a cancer survivor. In 2009, he was appointed by Michigan Governor Jennifer Granholm to be receiver of the Detroit public school system. He never stopped working even while he underwent surgery and treatment. At the time, he told hardly anyone, and he beat it.  

To this day, baseball is deep in Bob’s blood. He never did play professionally, but he was part of the team that brought professional baseball to the nation’s capital. Sure, he cheers for the Nats. But his heart will always be with the Dodgers.