Meet the Candidates

A large part of the Caucus' activities involves vetting and slating candidates for openings on Winnetka's four Boards - Village Council, Parks, Library, and Schools - and placing them on the Illinois Spring Ballot. 

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Rob Apatoff
Village Trustee

Rob Apatoff has served for the past 1.5 years as a Village of Winnetka Trustee.


Trustee Apatoff has served as President and CEO and Board member of FTD Companies Worldwide, and prior to that, CEO of Rand McNally.


Currently, Trustee Apatoff is Executive Director/Clinical Professor of the Executive Leadership Institute at Kellogg School of Business at Northwestern University, and serves as a senior advisor to Private Equity leader, TPG.


Trustee Apatoff's deep background in management, strategy, operations, marketing, development, and general management has helped the Village Council find “innovative and collaborative ways to restructure past Winnetka Village bonds, support our retail community and restaurants during Covid, more effectively preserve historic homes, bring vibrant new retail to town, and beautify our downtown business districts - all without raising the Village portion of the property tax levy on our residents."

Trustee Apatoff  believes the council must help keep Winnetka vibrant and moving forward while remaining  fiscally disciplined. 

A lifelong resident of Winnetka and graduate of New Trier and DePauw University, Rob and his wife Vicki, raised their two daughters in Winnetka, both of whom have returned to raise their families within the New Trier school district.

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kristina dalman
Village trustee

Trustee Dalman has been a practicing attorney for 29 years, as a land use and real estate lawyer. 


A graduate of University of Michigan Law School, Dalman currently is Vice President and Area General Counsel for PulteGroup, Inc.  where she is In-House Counsel supporting Pulte's homebuilding operations in the Midwest.


Prior to being appointed to the Village Council to fill the vacancy left by retiring Trustee Penny Lanphier, Dalman had served as Winnetka Plan Commission Chair, and on the Planned Development Commission.


Dalman also served on the 2013 Urban Land Institute Technical Assistance Panel that analyzed Winnetka’s Commercial Districts, and was a member of the Downtown Master Plan Steering Committee.

Trustee Dalman’s activities outside of Winnetka have included the Metropolitan Planning Council's Sustainable Development Committee, and the Urban Land Institute (ULI) Chicago District, Public Policy Committee.


Trustee Dalman brings to Village Council a strong understanding of municipal law and real estate development, and is “passionate about creating strong and vibrant communities that are valued by existing residents and desired by new residents.”


Trustee Dalman, her husband and three children and have lived in Winnetka since 2007.

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Kim handler
Village Trustee

Kim Handler is a CPA with a BA in Economics and Finance from University of Illinois and a Masters in Accountancy from DePaul University. She began her career at Price Waterhouse, then served as a Financial Officer with Kraft Foods responsible for finance, accounting and administrative functions at Worldwide R&D, and as VP of Finance for Strategic Hotel Capital.


Handler’s volunteer efforts include the boards of the Northwestern University Settlement House and Juvenile Protective Association, and numerous D36, church and neighborhood associations. She is a founding member of Your Winnetka, and an editor of Spot Checks, the organization’s newsletter.


Handler has served the Winnetka Caucus Council as Village and Schools committees Chair, Communications Chair, and Caucus Chair.


She is presently a Commissioner on Winnetka’s Zoning Board of Appeals and ZBA’s liaison to the Planned Development Commission.


Commissioner Handler brings to Village Council broad financial skills including financial reporting and analysis, budgeting, capital expenditure planning, and retirement planning, and believes that “at the end of the day, all policy decisions have financial implications; I will bring the financial skills to ask the right questions, analyze and understand these implications.”


Kim and her husband Tom have lived in Winnetka for 35 years, and raised their three children here, all of whom attended D36 and New Trier.

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Kate Casale
village Trustee (alternate)

Kate Casale MacNally earned a BA in Psychology and a JD from The University of Chicago.

Casale MacNally practiced commercial real estate law, and briefly worked as a legal recruiter. Following the birth of her first child, she stepped away from law to raise her family.


Since moving to Winnetka 4 ½ years ago, Casale MacNally has served on the Winnetka Caucus Council as a member and Chair, the Winnetka-Northfield Public Library District Board of Trustees, and the Willow Wood Preschool Board of Directors as Digital Communications Manager, Registrar, and President.

She is presently a Commissioner on Winnetka's Zoning Board of Appeals, serves on the Greeley Elementary PTO, and is a class parent for her daughter’s kindergarten.

Prior to moving to Winnetka, Casale MacNally volunteered extensively on the board of Step Up, a non-profit that helps girls from underserved communities become college-bound, and career-ready, and as an alumna volunteer for The College and The Law School at The University of Chicago.


Casale MacNally believes “a community only works if all who are able and interested use their skills, talents, and gifts for the betterment of the whole.”


Kate and her husband Andrew are the proud parents of two daughters, one in kindergarten at Greeley Elementary School, and another at Willow Wood Preschool.