Winsted City Council · Nov 3, 2026
Jessie
Cafferty
Jessie Cafferty, the incumbent, is running for Winsted City Council in the Nov 3, 2026 election; 4 candidates are running for 2 seats.
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The race · City Council
- 01Julie Weinbeck Baruch
- 02Jessie CaffertyYou’re reading
- 03Tim Storms
- 04Michael J Watroba
Background
- About
- Winsted City Council member and deputy mayor, with a term that expires December 31, 2026.
On the record: Jessie Cafferty
10 sourced01Taxes and budget1 sourced position
Voted yes on Resolution R-26-33 certifying a preliminary 2027 property tax levy of $2,347,959 (passed 5-0, September 2026).
Council voteCity of Winsted · Sep 15, 2026LinkHow the council voted
02Streets2 sourced positions
Voted yes on Resolution R-26-11 receiving the 2027 Infrastructure Improvement Project feasibility report and calling a public hearing (passed 4-0, April 2026).
Council voteCity of Winsted · Apr 21, 2026LinkHow the council voted
as recorded in the council minutes; not a direct quote
Asked why Zion Avenue would be rebuilt to its current width given the foot traffic it gets (February 2026 work session).
Own statementCity of Winsted · Feb 17, 2026Link
03Hainlin Park2 sourced positions
Voted yes on Resolution R-26-23 issuing a $1,685,000 general obligation tax abatement note and equipment certificate (passed 4-0, June 2026).
Council voteCity of Winsted · Jun 16, 2026LinkHow the council voted
Voted yes on Resolution R-26-22 approving a property tax abatement to repay borrowing for the park pavilion (passed 4-0, June 2026).
Council voteCity of Winsted · Jun 16, 2026LinkHow the council voted
04Equipment2 sourced positions
as recorded in the council minutes; not a direct quote
Asked staff to research how nearby cities buy and replace equipment, including buying a used vehicle (April 2026).
Own statementCity of Winsted · Apr 21, 2026Link
as recorded in the council minutes; not a direct quote
Said he feels the city has a lot of equipment for three employees and the city's cost for a replacement plow truck is significant even with the grant (October 2026 work session).
Own statementCity of Winsted · Oct 20, 2026Link
05Fire department1 sourced position
Voted yes on buying a new fire department rescue truck for up to $638,707.12 (passed 5-0, August 2026).
Council voteCity of Winsted · Aug 18, 2026LinkHow the council voted
06Brush site1 sourced position
Voted yes on Ordinance O-26-01 amending the 2026 fee schedule, including a commercial brush site access card fee (passed 4-0, April 2026).
Council voteCity of Winsted · Apr 7, 2026LinkHow the council voted
07Trails1 sourced position
Voted yes on awarding the 6th Street Trail Project base bid to Landwehr Construction for $371,557.25 (passed 4-0, June 2026).
Council voteCity of Winsted · Jun 16, 2026LinkHow the council voted
Every claim links to its source and was checked against it before publishing. How this guide works
Jessie Cafferty: their words and their votes on the same issue
Streets
In their words
Asked why Zion Avenue would be rebuilt to its current width given the foot traffic it gets (February 2026 work session).
Feb 17, 2026 ·as recorded in the council minutes; not a direct quote ·City of Winsted · Feb 17, 2026
On the record
Voted yes on Resolution R-26-11 receiving the 2027 Infrastructure Improvement Project feasibility report and calling a public hearing (passed 4-0, April 2026).
Apr 21, 2026 ·City of Winsted · Apr 21, 2026
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