Winthrop Police Chief Terrence Delehanty is the top paid town employee for calendar year 2018, taking home $182,984 including overtime and longevity.
While he diid serve as Town Manager for several months he took his police chief salary for pay and not that of a Town Manager.
Below is a list of the Top 50 employees and what they earned in calendar year 2018, according to their W2 forms.
Following close behind, and in the past he has topped the list, is police Lt. David Lessard who brought home at total of $169,826.
Then comes Superintendent of Schools Lisa Howard who earned $164,961.
Followed by the Fire Dept. employees Richard Swartz who made $148,182 and Fire Chief Paul Flanagan who earned $143,327.
In the sixth position on the list goes to Deputy Police Chief John Goodwin who took home $140,237.
Coming in seventh is Edwin MacDonald Jr. of the Fire Dept. who brought home $138,175. Then DPW Head Steven Calla with a check for $134,560.
Ninth on the list is police Lt. Nancy Dalrymple with $132,715 and the 10th person on the salary list is David Brown in the police Dept. with a check for $130,279. All top-50 on the list appear with breakdowns of their pay.
Highest Paid Municipal Employees in 2018
| Dept. Name | Name | TOTAL GROSS | YTD Reg | YTD Detail | YTD Detail OT | Total Other |
| Police Dept. | Delehanty Terence | 1,82,984.47 | 1,60,912.27 | 172 | — | 21,900.20 |
| Police Dept. | Lessard David | 1,69,826.90 | 72,217.28 | 33,776.00 | 3,240.00 | 60,593.62 |
| School Dept. | Howard Lisa | 1,64,961.57 | 1,58,730.77 | — | — | 6,230.80 |
| Fire Dept. | Swartz Richard | 1,48,182.86 | 1,29,230.76 | — | — | 18,952.10 |
| Fire Dept. | Flanagan Paul | 1,43,327.32 | 1,37,672.82 | — | — | 5,654.50 |
| Police Dept. | Goodwin John | 1,40,237.69 | 1,27,653.75 | — | — | 12,583.94 |
| Fire Dept. | Macdonald Jr. Edwin | 1,38,175.74 | 79,422.00 | 219.82 | — | 58,533.92 |
| DPW | Calla Steven | 1,34,560.30 | 1,32,054.42 | — | — | 2,505.88 |
| Police Dept. | Dalrymple Nancy | 1,32,715.72 | 66,200.23 | 8,016.00 | 667.5 | S7,831.99 |
| Police Dept. | Brown David | 1,30,279.33 | 55,030.69 | 31,904.00 | 2,041.50 | 41,303.14 |
| Police Dept. | Rogers Stephen | 1,25,991.38 | 62,483.33 | 1,204.00 | — | 62,304.05 |
| School Dept. | O’Connell Jennifer | 1,18,045.98 | 1,18,045.98 | — | — | |
| Police Dept. | Oyola Ignacio | 1,18,035.32 | 55,030.69 | 19,143.13 | 838.5 | 43,023.00 |
| Fire Dept. | Wiley William | 1,15,784.81 | 89,882.84 | 244.32 | — | 25,657.65 |
| Finance | Perez Michael | 1,15,153.74 | 1,13,076.90 | — | — | 2,076.84 |
| School Dept. | Grayson Constance | 1,13,968.79 | 80,301.81 | — | — | 33,666.98 |
| School Dept. | Crombie Matthew | 1,13,568.00 | 113,S68.00 | — | — | |
| School Dept. | Pearson Ilene | 1,12,876.92 | 1,12,876.92 | — | — | |
| Treasurer Collector | Ford Monica | 1,11,977.90 | 89,031.09 | — | — | 22,946.81 |
| Fire Dept. | Flynn Daniel | 1,11,573.90 | 63,639.40 | 266.22 | — | 47,668.28 |
| Police Dept. | Connolly Michael | 1,11,561.25 | 51,463.88 | 31,748.00 | 903 | 27,446.37 |
| School Dept. | O’Leary Andrea | 1,11,179.65 | 99,122.75 | — | — | 12,056.90 |
| Police Dept. | Feeley James | 1,07,144.46 | 62,483.33 | 12,668.00 | 1,569.00 | 30,424.13 |
| School Dept. | Curley Brian | 1,05,390.00 | 1,05,040.00 | — | — | 350 |
| Police Dept. | Crisafi Mary | 1,04,616.35 | 62,483.33 | 4,904.00 | 64.5 | 37,164.52 |
| Police Dept. | Ramadani Faton | 1,04,482.28 | 51,216.27 | 26,490.00 | 3,471.00 | 23,305.01 |
| Police Dept. | Bonavita Giulio | 1,01,065.37 | 55,030.69 | 15,308.00 | 1,677.00 | 29,049.68 |
| Fire Dept. | Calandra Stephen | 1,00,706.39 | 68,318.22 | 187 | — | 32,201.17 |
| DPW | Armitstead Aaron | 1,00,525.89 | 86,291.62 | — | — | 14,234.27 |
| Police Dept. | Armitstead Dawne | 99,692.03 | 55,030.69 | 5,619.65 | 496.5 | 38,545.19 |
| Fire Dept. | Vecchio Jr. William | 99,153.99 | 56,189.82 | 187.01 | 42,777.16 | |
| Police Dept. | Freeman James | 98,625.27 | 38,265.81 | 15,592.00 | 1,084.50 | 43,682.96 |
| School Dept. | Grimes Norah | 98,483.45 | 97,083.48 | — | — | 1,399.97 |
| Police Dept. | Hickey Sean | 97,023.91 | 55,Q30.69 | 16,684.00 | 2,322.00 | 22,987.22 |
| Police Dept. | Hagemeister William | 96,747.91 | 55,Q30.69 | 26,552.00 | 2,794.50 | 12,370.72 |
| School Dept. | Mauro Karen | 96,427.70 | 77,213.08 | — | — | 19,214.62 |
| Police Dept. | Hickey Jr. Arthur | 96,035.75 | 62,483.33 | 2,3S2.00 | 432 | 30,768.42 |
| Town Clerk | Vitale Carla | 95,798.09 | 79,664.92 | — | — | 16,133.17 |
| Police Dept. | Bettano Nicholas | 95,268.08 | 49,989.81 | 16,470.00 | 2,724.00 | 26,084.27 |
| Assessing | Roche Stephen | 95,000.10 | 95,000.10 | — | — | |
| Police Dept. | Perrin Sean | 94,588.88 | 55,030.69 | 15,587.30 | 709.5 | 23,261.39 |
| School Dept. | Capasso Michael | 94,205.80 | 92,862.12 | — | — | 1,343.68 |
| School Dept. | Preble Anita | 94,101.34 | 82,366.22 | — | — | 11,735.12 |
| School Dept. | DeFelice Michael | 93,851.31 | 80,301.81 | — | — | 13,549.50 |
| Finance | Zaleski Elizabeth | 93,750.80 | 91,321.42 | — | — | 2,429.38 |
| School Dept. | Preble Jason | 91,915.66 | 77,213.08 | — | — | 14,702.58 |
| School Dept. | Franzese Justeen | 91,104.00 | 91,104.00 | — | — | |
| School Dept. | Murphy Kariann | 91,104.00 | 91,104.00 | — | — | |
| Fire Dept. | O’Brien Patrick | 90,705.47 | 55,207.92 | 152.82 | — | 35,344.73 |
| Police Dept. | Delehanty Sean | 90,507.45 | 55,030.69 | 16,168.00 | 1,161.00 | 18,147.76 |
| School Dept. | D’Amico Kathleen | 90,236.60 | 83,062.59 | — | — | 7,174.01 |