1976-2001A Change of Course in City Government: Bill SquillacePeople and Communities, Government and Public Service, City Government, 400 Stories Project

The 1970s, ‘80s, and ‘90s were periods of change and transition in Gloucester city government, especially in the mayor’s office.

The following is a snapshot of the unusual circumstances that led to the election of the first five mayors at the wheel of city government from 1976 through the end of the 20th Century.

In 1976, the citizens of Gloucester voted to change their form of city government and elect mayors to run the city. Prior to that time, and for nearly a quarter of a century, city managers were hired by the city council to manage city business, and mayors were elected by the city council from within their own ranks to serve as the ceremonial head of city government. This City Charter change gave citizens more direct control over their city government and the ability to elect a new mayor every two years as they saw fit.

Leo Alper was the first mayor to be elected in a special election after the City Charter was changed in 1976. Prior to his election, Leo served as a member of the Gloucester City Council and owned a laundry. He was a shrewd businessman known for his rough around-the-collar, robust, and sarcastic sense of humor.

Leo brought national attention to Gloucester with his opposition to Reverend Sun Myung Moon and the Unification Church, “The Moonies,” who were attempting to take over the city’s waterfront and fishing industry. Leo was interviewed on the TV program “60 Minutes” by correspondent Morley Safer and quoted as saying, “The moonies will have strap marks across their ass before they get anywhere in this town.” One thing you could be sure of about Leo. He loved Gloucester and being mayor.

After seven years in office and approaching the age of seventy, Leo said he would not seek re-election. Hearing the news, Gloucester’s State Representative, Dick Silva, announced his intentions to enter the upcoming mayor’s race.

Dick had served in the Massachusetts State Legislature for thirteen years and was best known for his leadership in establishing the 200-mile limit that protected fishing grounds off the coast of the United States.

Before Dick entered politics, he was a technician for the Massachusetts Electric Company and, in 1963, was elected to the Gloucester School Committee. In 1970, he was elected by the citizens of Gloucester and Cape Ann to serve as their State Representative. He was also active in several community groups and organizations.

In a surprise move, just as the 1983 election season was about to begin, Leo changed his mind and announced he would be running for re-election after all. This was news to Representative Silva, who did not expect to battle Leo for the top job in city government.

I did not know Representative Silva at the time, but Leo was a friend who, three years earlier, appointed me to serve as Gloucester’s Representative to the North Shore Regional Vocational /Technical School Committee. I joined the Alper re-election campaign team and worked to keep Leo in office for two more years. Many thought it would be an uphill battle against his formidable opponent who had a long record of service to the people of Gloucester and was well respected in the community.

It was a hard-fought campaign, with Leo throwing all the dirt he could muster up at Dick Silva, but none of it stuck. After all the votes were counted, Dick defeated Leo by a large margin.

In retirement, Leo kept busy helping out in his son Bobby’s pharmacy and antiques store located across the street from my antiques store in Magnolia. This provided several opportunities to chat with Leo about the politics of the day and to hear him complain about everything he thought Dick Silva was doing wrong.

During one of these many chats, Leo asked me if I had any interest in running for public office. I responded, “Why Leo, whatever gave you that idea?” He said in his usual sarcastic manner, “Cut the crap; you have been running ever since you landed back in Gloucester!”

Four years earlier, I returned home to Gloucester to begin a new chapter of my life after living in Alexandria, Virginia, and working in Alexandria’s city government for nine years. My plans for moving back home included opening a chain of antiques and home furnishings stores throughout the North Shore, getting involved in community activities, settling down, and having a family. I was also interested in politics and indeed had thoughts of running for public office someday.

Most of all, I missed the special quality of life I had known in Gloucester and Cape Ann, where I grew up and where my family roots ran deep. My great-grandfather, schooner Captain Robert B. Porper, arrived in Gloucester from Nova Scotia during the mid-1800s to fish the rich waters off of Cape Ann out to the Grand Banks and beyond.

Leo and I discussed various political races coming up, including the race for State Senator, which interested me the most. Leo’s opinion was that Republican State Senator Bob Buell had been in office too long, was rarely seen around town, and hadn’t done much for Gloucester. After talking with others, I entered the State Senate race with Leo lending a hand.

After all the votes were counted, Senator Buell won by a large margin and taught me a hard and expensive lesson that popular incumbents were hard to defeat.

Feeling down in the dumps and discouraged, I began to reassess my career plans and had thoughts about returning to public service.

I saw a job advertised in the Gloucester Daily Times for the position of purchasing agent for the city of Gloucester. The job looked interesting, and I had the right qualifications, except for one – Dick Silva was mayor and the very man I had worked against during the previous mayoral election. As they say in politics, “To the victor goes the spoils, “and I was not on the winning team.

I went across the street for coffee with Leo and jokingly mentioned the purchasing job. The first words out of Leo’s mouth were, “If you think Dick Silva is going to give you a job, you have rocks in your head!”

Perhaps Leo was right; however, I learned a little about Dick during the mayor’s race, and he seemed like a decent, honest, and fair-minded person who might view my application objectively and not based on my politics.

My appointment to the Regional/Technical School Committee by Leo had not yet expired. I was still required to provide updates on regional school operations regardless of who was mayor, and my update to Mayor Silva was overdue. This might also give me the opportunity to mention the purchasing job.

I met with Mayor Silva, and after the update on the regional school, I asked him how he liked being mayor. He said the commute was easier, but there were more moving parts to running city government than he had to deal with at the State House. I mentioned that I saw his ad for a city purchasing agent and had been thinking about resuming my career in public service. He said to stop by his assistant’s office, Jeff Zager, who could provide more information about the job. I met with Jeff, and he gave me an application to fill out and said he would contact me. At least I didn’t get laughed out of City Hall.

A few weeks passed, and there was no news about the purchasing job. I finally called Jeff, who said he was glad I called as he had news for me, “Mayor Silva would like to offer you the purchasing job.” I almost dropped the phone.

I couldn’t wait to see the expression on Leo’s face and headed across the street. “Hey Leo, I don’t have as many rocks in my head as you thought; Dick Silva just offered me the purchasing job”!

My appointment as city purchasing agent was confirmed by the Gloucester City Council. A few days before I was scheduled to report to work, I joined friends Margaret and Harold Woodruff with Leo Alper for dinner at the Patio restaurant in Magnolia. Just after we arrived, Mayor Dick Silva and his wife Janet walked through the door and sat down just a few tables away. I felt uneasy because these two political rivals were within close range, and Leo was still bitter about his defeat. The last thing I needed was for Leo to make a wisecrack causing Mayor Silva to have second thoughts about hiring me. Margaret and Harold sent drinks to Dick and his wife, and we lifted our glasses in their direction, with Leo begrudgingly joining in and agreeing to take a photo with Mayor Silva.

Things were going fairly well in the purchasing department; however, Jeff Zager resigned from his position as chief administrative officer and administrative assistant to the mayor to become a town manager in a neighboring community. Mayor Silva asked me to consider taking Jeff’s position.

City Clerk, Freddy Kyrouz, had become my trusted advisor about everything to do with Gloucester city government. He was an old friend of my grandmother’s, Marie South, going way back to when they both worked on Main Street. Freddy thought I would be a fool to give up a lifetime job in the purchasing department for one that could change every time a new mayor was elected because new mayors usually selected their top aid. I took Freddy’s advice and stayed put in the purchasing department.

Mayor Silva hired Jeff’s replacement, but it soon became clear to him that he had hired the wrong person for the job. He asked me once again to consider taking the position. This time, I felt more confident that if he left office, I could land another position somewhere in government. Plus, the pay increase would be helpful for a newly married man with a baby on the way. A city council vote confirmed my appointment, and I moved into an office next to Mayor Silva, with Freddy Kyrouz shaking his head from across the hall.

It was a pleasure working by Mayor Silva’s side. He was kind, humble, and quiet, unlike his predecessor, Leo Alper. I can’t imagine Dick Silva saying he would take a strap across anyone’s ass.

Mayor Silva was in his second term of office and decided not to seek a third term. He had reached retirement age and wanted to spend more time with his family. Once the news hit the streets, several members of the City Council announced their intentions to enter the race for mayor. I had a fairly good relationship with most of the city councilors running but wasn’t given any guarantees that I would be able to keep my job, all except for one, Dottie Talbot. The words of Freddy Kyrouz started to echo in my ears.

A few people suggested that I should enter the mayor’s race. I had run for the State Senate a few years before and lost the race but had a decent showing in Gloucester. However, I had given politics a try and wasn’t sure I wanted to roll the dice again in what was sure to be a hotly contested race.

I would have liked to have consulted with Leo Alper about running, but unfortunately, he passed away that winter while vacationing in Florida. If he was still around, I’m sure he would have said, “Over my dead body, if anybody is running, it’s going to be me!”

Mayor Silva urged me to run but said he would stay out of it until after the preliminary election. With words of encouragement from Mayor Silva and support from friends and family, I joined the long list of mayoral candidates.

Peter Bearse, Ph.D., and I made it beyond the preliminary election and now would be facing off against each other in the final. Mayor Silva gave me his endorsement, and with the support from the Alper and Silva camps and a fleet of volunteers, I was elected the 54th mayor of Gloucester (in 1988). It was a proud moment for me and my family as city clerk Freddy Kyrouz administered the oath of office.

I was re-elected to a second term and ran unopposed except for a challenge from perennial candidate Dan Roberti. Dan was not considered a serious candidate but was a well-loved fixture in city elections. He would stand on Tally’s Corner blowing his trumpet while handing out his homemade bumper stickers to passing motorists.

In a surprise to many, Dan received a larger vote than expected but fell well short of victory. It was a clear message to me that voters were not happy. During my first term, water and sewer rates were increased, and new solid waste disposal fees were required to meet state and federal environmental regulations. Layoffs were also required due to cutbacks in state aid.

During my second term of office, a friend asked me to meet Republican Joe Malone, who was running for State Treasurer. I met with Joe, who had fresh ideas and pledged to reform state government, which was long overdue. However, I told him I could not support him because State Senator Dick Kraus was also running for State Treasurer and married to Gloucester’s State Representative, Pat Fiero. I didn’t think supporting one of his potential opponents would be wise. Joe said if Senator Kraus didn’t make it beyond the primary, would I recon-sider? I said I would give it serious thought.

Senator Kraus was defeated in the primary, and Joe Malone was soon on the phone again, asking for my support. He seemed sincere about reforming state government, and I thought it was time for some new blood on Beacon Hill and was happy to support him.

Evidently, the voters of Massachusetts, including many other Democrats, agreed and elected Republicans Joe Malone as State Treasurer, Paul Cellucci as Lieutenant Governor, and Bill Weld as Governor.

Shortly after the state election, I received a call from a member of Joe Malone’s transition team who asked if I was interested in serving within Joe’s administration. I had no idea what role I might play but was curious and agreed to meet with Joe and his transition team, including consultants from Mitt Romney’s, Bain and Co., who were helping Joe put together his staff.

I was offered an Assistant State Treasurer position which sounded like a challenge and came with a salary nearly double what I was being paid as mayor. I certainly had a lot to think about.

Once again, I asked Freddy Kyrouz what he thought about taking the state job. Freddy was quoted in the Gloucester Daily Times as saying he would have me committed to Danvers State Mental Hospital if I didn’t take the job.

I was still concerned about letting down my supporters and the people of Gloucester who elected me. Freddy said, your friends and supporters will be happy for you, but your enemies and those who were never with you will not be so kind.

My former boss, Mayor Silva, said it was a wonderful opportunity that I might never have again and to think of my family. It also seemed like an opportunity to continue serving the city of Gloucester but at the state level, where several state treasury functions were carried out that affected cities and towns. With mixed emotions, I resigned from the office of mayor and joined the Administration of State Treasurer Joe Malone in 1991.

The City Charter had a provision that called for the city council to elect an interim mayor if a vacancy occurred during the second year of a mayor’s term of office. If the vacancy occurred during the first year of a term, then the citizens of Gloucester would have had to go to the polls to elect a new mayor. That not being the case, it was now up to the City Council to elect an interim mayor to serve the remainder of my term.

It soon became clear that several City Councilors wanted to be interim mayor and voted for themselves in a series of roll call votes. After several rounds of voting, no city councilor received the required majority of five votes needed to become interim mayor. The Gloucester Daily Times ran a cartoon by Phil Bissell showing all the City Councilors grabbing for the mayor’s chair as I departed for the State House.

Finally, City Councilor Bruce Tobey stepped up and pledged not to run for mayor in the upcoming fall election. This removed the appearance of an advantage an interim mayor might have if they ran in the fall.

Bruce received a majority of votes and was elected interim mayor by the City Council. Bruce was an attorney who had served as city solicitor within the Alper administration and, together with his experience as a city councilor, was well prepared to take over the reins of city government. Bruce kept his word and did not run for mayor in the fall election and instead ran for School Committee. City Councilor Bill Rafter ran for mayor and was elected the 55th Mayor of Gloucester after defeating City Councilor Gus Foote.

After one term as a school committee member, Bruce Tobey ran for mayor and defeated Bill Rafter to become the 56th mayor of Gloucester.

In addition to serving as interim mayor, Bruce was elected and served four full terms as mayor until the end of the 20th Century to 2002. He re-entered city government in 2006, was elected to the city council, and served until 2014. Bruce continues to serve the city as a tri-chair of the Gloucester 400 Anniversary Committee.

Yes, the 1970s, ‘80s, and ‘90s were times of change and transition in Gloucester city government and the mayor’s office. It was an honor and privilege to have known and worked with the public officials who were at the wheel of Gloucester city government during this time. Most of all, I am grateful to the people of Gloucester for the opportunity to witness and participate in this small piece of Gloucester’s 400+ year history.

Happy 400th Anniversary Gloucester!


This story contains public information and is well documented in official city records located in the Gloucester City Clerk’s Office, as well as in newspaper accounts published in the Gloucester Daily Times. Therefore, I have not included footnotes which I feel would serve little purpose.

The quotes are from my personal recollections based on in-person conversations I had with the persons mentioned in the story. Each of them were friends or professional associates, including: former Mayors Leo Alper and Dick Silva, former City Clerk Freddy Kyrouz, and former assistant to Mayor Silva, Jeff Zager.


Bill Squillace is the great-grandson of schooner Captain Robert B. Porper, who arrived in Gloucester during the mid-1800s from Nova Scotia. Bill graduated from Gloucester High School in 1966 and was elected the fifty-fourth mayor of Gloucester in 1987, and re-elected in 1989. He resigned from office in 1991 to accept the appointment of Assistant State Treasurer for the Commonwealth of Massachusetts. He has one daughter, Kathryn.


Credit for the cover photo of Gloucester’s city hall and inner harbor goes to author William Squillace. It looks like a painting, but it’s William’s photo taken from Rocky Neck, circa 1992.

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