Esslie-Frenia Law June 2023 Leaderboard

Contest in Copake goes on the roads this year


COPAKE — The only political race at the town level is the one for highway superintendent this November.

Unexpectedly last November, then highway superintendent Larry Proper, a Republican, resigned and recommended that the Town Board appoint his deputy, William H. Gregory, Jr., also a Republican, to fill the department’s top spot. The board agreed.


At that time, Mr. Proper had served as highway boss for 11 years and had two years remaining in his four-year term. When he left the department, Mr. Proper was paid an annual salary of $25,355.50 by the town. In March 2008, he announced he had taken on a full-time job with the Taconic Hills School District. Mr. Proper continued to fulfill his duties as Highway Department chief by putting in hours both before and after his job at the school.

Since Mr. Proper was not on the job full-time for the town, he told the board he did not expect the town to continue to pay him his full annual salary of $50,711 and he let the board decide a fair amount to pay him. The board voted to cut his salary in half.

When Mr. Gregory took over as highway boss last November, his pay was increased to the full salary for the position and, as a cost saving measure suggested by Mr. Proper, the board did not hire anyone to replace Mr. Gregory.

Both William C. Jamieson, 56, an enrolled Conservative endorsed by Town Democrats, and Mr. Gregory, 44, an enrolled Republican endorsed by his party as well as Conservatives and the Independence Party, are running to fill the one-year still remaining in Mr. Proper’s term.

The issue of whether the highway superintendent position is a full-time job with a full-time salary, was raised by Mr. Jamieson, who shortly after his nomination noted in his campaign literature, “It has been proven in the last two years that the highway superintendent position is a part-time job.” Drawing on Mr. Proper’s example, Mr. Jamieson vowed to “return the position from full to part-time, cutting the salary in half with no benefits, a tremendous savings to the town.”

But Mr. Jamieson told The Columbia Paper this week that since those early days in the campaign, he has changed his mind about the part-time idea, and for many months has let voters know he will be a full-time highway boss, though he would take only half the allotted salary. “Isn’t that a whole lot better for the Town of Copake?’ he asked.

Mr. Jamieson is retired with 31 years of experience with the Columbia County Highway Department.

He was born in Hudson and graduated from Taconic Hills High School in 1973.

“I have lived in Copake most of my life. I grew up here. My wife and I went to the two-room schoolhouse on Empire Road. Copake has always been home.

“As a road foreman at the county, three years at the Copake outpost, I managed the same concerns as those faced at the town level. I know the area; I know the roads and the people.

“I want to give back to my community. I will work full-time and take only half the salary established for this position. I will trim spending wherever possible without sacrificing services or quality,” Mr. Jamieson said in his statement of issues.

Mr. Jamieson has one grown son, Cameron. He and his wife, Diana, live on Mountain View Road.

Mr. Gregory was born in Hudson and graduated from Taconic Hills High School in 1984.

He attended Columbia-Greene Community College for two years and has taken seven courses sponsored by Cornell University on local roads.

Mr. Gregory worked for the Hillsdale Highway Department from 1988 to 2004 and since then has worked for the Copake Highway Department.

He is a volunteer emergency medical technician for the Community Rescue Squad. He volunteers for the New York/New Jersey Trail Conference as a trail maintainer on the South Taconic Trail and for the Berkshire Chapter of the Appalachian Mountain Club as a corridor monitor on the Appalachian Trail.

“For the last 11 months, I have had the great pleasure to serve as the Town of Copake Highway Superintendent. I am committed to this job and our community. Whether maintaining our roads and equipment or building strong relationships with our Town Board and the public, I will always place the interests of our town first.  I have taught both of my children that hard work will be rewarded.  I firmly believe this statement and ask for your support on Election Day, allowing me to continue the most rewarding job I have ever had, the Town of Copake Highway Superintendent,” Mr. Gregory said in his issue’s statement.

He and his wife, Korina, have two sons, Michael, 22, and Ryan, 13. They live on County Route 7.

Voters will not cast their ballots to fill a vacancy for a third assessor position, because a majority of Town Board members, all Republicans, voted to dump the three-elected-assessor system in favor of a sole appointed assessor in September.

Democrats had nominated Veronique Fabio to run for that position. There was no other nominee.

To contact Diane Valden email

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