Recovery and Reentry – R&R redux for Winning Ways clients

Today Magazine Online

3 hours ago

6 min read

• Nonprofit Assists With Incarceration Reentry, Substance-Use Recovery

Bruce William Deckert

Editor-in-Chief

Today Magazine CT

• Winning Ways came on the news radar of Today Magazine at an event hosted by the Avon-based Raymour & Flanigan, in the heart of Connecticut's Farmington Valley — the nonprofit's executive director has provided an exclusive interview for Today Magazine CT readers

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Incarceration and substance use are interrelated social and psychological issues that impact human communities across the spectrum: nations, states, counties, cities, towns and every other conceivable municipal configuration around the world.

A noteworthy nonprofit based in Connecticut is celebrating its 10th anniversary throughout 2026. Yes, if you are so inclined, you can send a birthday message and/or present to Winning Ways as 2026 winds down — in conjunction with the trifecta of sacred-and-secular holidays that complete the calendar year across the United States of America.

Indeed, New Haven-based Winning Ways Inc. is sharing a major milestone this year with the USA — in case the significance of this national milepost is escaping your awareness as we speak, the United States is of course observing a yearlong celebration of its 250th anniversary in honor of the signing of the Declaration of Independence in July 1776.

Further, in case the holiday trifecta referenced above is unclear, here is some clarity: Halloween, Thanksgiving and Christmas. Naturally, other significant jubilees are celebrated as each year nears completion — including All Saints' Day, Hanukkah and Kwanzaa — so feel free to insert your holiday of choice here.

The Winning Ways website explains the organization's mission this way: "to foster the success of the formerly incarcerated or those seeking recovery in underserved communities" — followed up by this statement of a cogent hope: "We help empower individuals to live meaningful lives and overcome histories of trauma."

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• Editor's Note — The R&R initials in the headline for this story typically refer to rest and relaxation — executive director Kevin Paulin has answered this exclusive Q&A on behalf of Winning Ways, a nonprofit that puts a distinctive and supportive spin on R&R

Winning Ways Inc.

Location – Grand Avenue • New Haven • Connecticut

– Previous Location – North Main Street • Branford CT

Phone – 203-200-0249

• Email – kevin@winningwaysct. org

• Website – www.winningwaysct.org

• Social Media:

Facebook – Winning Ways Inc.

Instagram – @winningwaysct

LinkedIn – Winning Ways Inc of Connecticut

• Year Established — 2016

• Mission

Winning Ways Inc. is a community-based nonprofit dedicated to expanding access to vital resources for individuals and families impacted by incarceration, substance use, trauma and economic instability. Grounded in lived experience and trauma-informed, evidence-based practices, we empower individuals to achieve long-term stability, recovery and economic mobility.

• Slogan — Together We Win

• Most fulfilling aspect of your work?

The most fulfilling aspect of our work is witnessing transformation in real time. Every participant represents a story of resilience — individuals rebuilding their lives after incarceration, strengthening their financial stability and reconnecting with their families. Seeing that shift from uncertainty to confidence is what drives our work every day.

• Your biggest obstacle, and how you overcome it?

One of our greatest challenges is meeting the growing demand for services with sustainable funding. As the need for trauma-informed reentry and recovery support increases, we continue to strengthen partnerships, pursue diverse funding opportunities, and demonstrate measurable impact to ensure our programs remain accessible and effective.

• Most satisfying accomplishment?

A defining accomplishment has been the growth and impact of The Winning Circle Series, our trauma-informed model integrating financial literacy, workforce development, expressive arts and peer mentorship. From 2023 to 2025, the program served nearly 1800 participants, reflecting both the demand for and effectiveness of holistic, community-based support.

• Goals for the next 1-5 years?

• Strengthen our presence at our New Haven site as a centralized hub for reentry and recovery services

• Expand our trademarked The Winning Circle Series to reach more communities across Connecticut

• Increase access to financial empowerment and workforce development pathways that support long-term economic mobility

• Volunteers — how many and opportunities to serve:

We engage a dedicated and growing network of volunteers, including 10 core community volunteers, 7 college interns and a Yale Fellow placement. We receive interns from institutions such as Southern Connecticut State University, Yale University, the University of New Haven and Albertus Magnus College, while Federal Work Study students are placed through the University of New Haven.

Students participate both onsite and through offsite placements, supporting program facilitation, outreach, event coordination and administrative efforts. We also operate as a VITA (Volunteer Income Tax Assistance) site, where 4 trained volunteers provide direct financial-empowerment services. As our programs expand, we continue to offer meaningful, hands-on opportunities for individuals to contribute to trauma-informed work that directly supports people in recovery and reentry.

• Anecdote that illustrates how you accomplish your mission:

One participant came to us after incarceration facing unemployment, financial instability and uncertainty about the future. Through our programs, this person engaged in financial literacy education, workforce development training and peer support. Over time, the participant secured employment, realized an improved financial situation, and became more confident in navigating life’s challenges — demonstrating how access to the right resources can create lasting change.

• How closely do you work with other agencies/nonprofits?

At Winning Ways, collaboration is not optional — it is essential, because together we win. We work closely with a network of reentry, behavioral health, workforce and academic partners to address systemic barriers and deliver coordinated, trauma-informed support. This collective approach allows us to maximize impact and create sustainable pathways to stability for those we serve. Also — we’re part of a formal statewide network called Connecticut's Reentry Community.

• Interesting stats and numbers associated with your nonprofit:

• Nearly 1800 participants served through The Winning Circle Series from 2023-2025

• Over 1000 individuals engaged annually in programming across reentry, recovery and financial-empowerment initiatives

• More than 1000 participants engaged in expressive arts programming through Spit & Paint

• Besides donations, how is your work funded?

Our work is supported through grants, corporate partnerships, program-based funding, and collaborations with community and institutional partners.

• What was your operating budget in your most recent fiscal year?

Approximately $220,000 — with continued growth to meet increasing community needs

• What is the salary range for your employees and management?

$35,000 to $80,000 — depending on role and experience

• Number of employees:

• Full-Time: 3 — Part-Time: 2

• Employees — names and titles:

• Dr. Kevin Paulin — Executive Director

• Wilford Charles — Creative Arts Director

• Sarah Hoffman — Intern

• Derrick Midy — Administration Support

• Jordan Paulin — VITA Site Supervisor

• Robbia J. Williams — Program Facilitator

– Editor's Note — info from LinkedIn and the Winning Ways website complements the employee info provided by Kevin Paulin

• Founders — Winning Ways was established in 2016 by Kevin Paulin, Ben Backes and Andrew Redenti

• What do you appreciate most

about Connecticut's Farmington Valley?

The strong sense of community

and the region's commitment to

supporting nonprofits and

collaborative solutions that

improve quality of life.

• Today Magazine covers news of interest statewide, with a focus on the Valley towns: Avon • Canton • Farmington • Granby • Simsbury

• What do you appreciate most about the state of Connecticut?

Connecticut's network of community organizations, service providers and public-private partnerships creates meaningful opportunities to address complex social challenges and expand access to resources for underserved populations.

• What constructive change would you like to see in the Valley and CT?

We would like to see continued investment in trauma-informed care, behavioral health services and reentry support systems, along with expanded access to economic opportunities for individuals impacted by incarceration and recovery.

• Further comment and/or info:

Winning Ways continues to build momentum through The Winning Circle Series, our core trauma-informed model that integrates financial literacy, workforce development, expressive arts and mentorship.

As we grow, we are placing an increased focus on engaging youth — creating early pathways to financial empowerment, career readiness and emotional well-being. By expanding youth-centered programming within The Winning Circle Series, we aim to interrupt cycles of trauma and create long-term opportunities for the next generation.

Our commitment remains to meet individuals where they are and provide the tools, support and community needed to thrive — because together, we win. +