ToquiNotes: The 10-Year Anniversary of the Passing of City Man whose Bridgeport Impact is Immeasurable
By Jeff Toquinto on February 07, 2026 from ToquiNotes
Well before Richard “Tiny” Grimes became the Bridgeport Public Works Director, he remembers getting lessons on a regular basis about things most people in Bridgeport may not know about.
“I remember one day Jeff Grogg and I were sent out tell to find a certain thing. We were told to find this curb box on Philadelphia Avenue. We found it, and we were quizzed when we came back to the department as to what it was,” said Grimes. “We didn’t know where it went to.”
As it turned out, there was an answer for that box at the intersection on Stout Street. It was feeding two houses going back up Philadelphia
Avenue. And as it turned out, the same person providing the answer was the same person quizzing the workers.
Avenue. And as it turned out, the same person providing the answer was the same person quizzing the workers.
The person is a familiar name to many in the city. For those who do not know it, the name should be.
It was Dellot "Dale" Shields. About everyone called him Dale. Yesterday, Friday, Feb. 6, was the 10-year anniversary of his passing at the all too early age of 58.
Although I was not a close friend of Shields, my work kept me in contact with him for many years. Trust me when I say this, there are few individuals that provided as much value to the City of Bridgeport than Shields did during his 37 years working for the city. He retired as the Superintendent of Public Works in September of 2013.
The value? It was knowledge. It was intimate knowledge. It was knowing where every single piece of infrastructure that made Bridgeport work was located, when it was installed, and what needed to be done if it did not work.
Grimes worked under Shields. He knew what Shields was doing prior to his retirement with those surprise trips. He was trying to make 
sure those who followed had at least a fair handle on a treasure trove of Bridgeport knowledge few, if any, possessed.
sure those who followed had at least a fair handle on a treasure trove of Bridgeport knowledge few, if any, possessed.
“The knowledge he had can’t be replaced. I think that’s why Dale was hard on us at times, not bad, but just making sure it was right. If you stayed, and most of us did, you learned,” said Grimes. “Those trips to find stuff was right before he left. It was frequent and it helped when he was gone, and still helps to this day.”
Grimes was not the only one who knew how important Shields was to the city then and its ongoing prosperity now. Count interim City Manager Joe Shuttleworth among the group.
“He was a fixture, and he knew everything. I just had a conversation about institutional knowledge, and how hard that is to replace, especially when things go wrong,” said Shuttleworth. “His instructional knowledge, he passed a lot of it along to Tiny, Jeff Grogg, Rick Moore, and so many others. That knowledge, all these years later, is still paying dividends for Bridgeport.”
Shields, a Bridgeport High School graduate, started at the bottom and climbed his way to the top. Grimes, who followed the same path, said that route is one that Shields took advantage of to the benefit of his department and the community.
“He paid attention to every job, every detail. He learned where everything was in the city. You want to know if there was a water or sewer line somewhere that may not be showing on a map, Dale Shields knew if it was there or not. If you had a question about the city, he was the one with the answer,” said Grimes.
Grimes’ statement is not hyperbole. My interactions with Shields were generally for those very reasons. Multiple city officials I interviewed would often say, and I’m paraphrasing, “Let me check with Dale and get back with you,” or “Give Dale a call. He’ll know the answer.”
That did not just happen a few times. It happened dozens of times. It happened every month of every year when Shields was working and I was covering Bridgeport. I do not ever recall getting an “I’m not sure” response from Shields on any question directed his way. I learned quickly who to call for anything I was not sure about. If you were around him, you learned.
“It didn’t take long, once working for Dale, to appreciate what he was doing because you learned. Years later, you really appreciate it,” said Grimes. “He was a great boss to work for because you saw he cared about the city and his staff. I try to emulate some things because the way Dale did things is the way all the guys that worked for him that are still here learned to do things.
“I always felt like people wanted to work for him and with him. We’ve seen a lot of people in this department stay a long time and it’s because they started with Dale or came in and were taught with the same methods Dale taught us,” said Grimes.
Staying long at the city’s public works department is, again, not hyperbole. Grogg and Moore, both foremen, have been with the city for 43 and 27 years, respectively. Grimes is approaching his 29th year with the city.
“It doesn’t seem that long ago since Dale passed. You know, you couldn’t have asked for a better guy,” said Grimes.
Shuttleworth said he was easy to work with between the departments. If Parks and Recreation needed help, he said Shields was not just there, but a pleasure to be around.
“Dale had the personality that was perfect because he was welcoming, funny, and had an inviting personality,” said Shuttleworth. “At the same time, he got things done. You look around and you see Dale’s fingerprints on how things have gone, especially with anything done in public works.
“He helped build a lot of careers in this city and put in the foundation for so much of what you see,” Shuttleworth continued. “It’s been more than a decade since he retired and those that knew him knew just how valuable he was. We’re all beneficiaries of his commitment to Bridgeport.”
Editor's Note: Top photo shows Dale Shields, right, with former Parks and Recreation Director and current City Council member Don Burton working on an issue at Compton Park, while Shields is shown in the second photo. Bottom photo, from Feb. 10, 2016, is part of the funeral procession as he was on his way to be laid to rest at the Bridgeport Cemetery.
