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  1. Professionals

Olga Loy

Partner

Chair, Tax Practice

Chicago

+1 312-558-6338

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  • Overview
  • Experience
  • Credentials
  • Insights & News

Olga concentrates her practice on tax and structuring aspects of private equity, venture capital and SBIC fund formation and complex business transactions, including mergers, acquisitions, buyouts, recapitalizations, debt and equity restructurings, and executive compensation.

Serving as the chair of Winston’s Tax Practice, Olga represents funds and fund sponsors in tax structuring, negotiating, and forming private equity and venture capital funds. She plans and structures other complex business transactions, including corporate mergers and acquisitions, leveraged buyouts, recapitalizations, and venture capital investments. Furthermore, she represents large public and private corporations on tax structuring of IPOs, SPACs, spin-offs, debt restructurings and general tax planning.

Olga regularly represents large and mid-size private equity funds and their management companies. These clients invest in North America, Europe, and Latin America. She also advises real estate funds and investors in tax structuring matters, including REIT counsel and planning and cross-border analysis.

Additionally, Olga is an adjunct professor at the University of Illinois College of Law, where she teaches a course on tax structuring of private investment funds and a lecturer at the Venture Capital Institute, where she teaches a course on venture capital funds and investments. 

The Legal 500 US sources describe Olga as "an outstanding partner with deep technical tax knowledge, effective administration of client matters, billing transparency including adherence to budgets and bringing the appropriate individuals with the technical expertise on to client matters." 

Recent Experience

Winston Represented Modern Aviation in its Acquisition of Puerto Rico FBO LLC
ClearCompany Sale to Gemspring Capital Management
Volery Capital Management Sale to Sustainable Development Capital
Digital Virgo Business Combination with Goal Acquisitions Corp.
5E Advanced Materials, Inc. Convertible Notes PIPE Offering
SunCap Acquisition of Adventure Forest, LLC
Prime Number Acquisition I Corp. Closes IPO
TradeStation Announces Business Combination with Quantum FinTech
Battery Future Acquisition Corp. Closes US$345M IPO
Citadel Defense Co.'s Acquisition by BlueHalo
View All Related Matters

  • Recognized by Lawdragon’s "500 Leading Global Tax Lawyers" (2025)
  • Recognized in The Legal 500 US for Tax (2019–2022, 2024)
  • Listed in Lawdragon’s “500 Leading Dealmakers in America” (2021–2024)

Capabilities

Transactions
Private Investment Funds
Mergers & Acquisitions
Private Equity
Tax
Secondaries & Liquidity Solutions
Financial Services
Cryptocurrencies, Digital Assets & Blockchain Technology

Recent Experience

Winston Represented Modern Aviation in its Acquisition of Puerto Rico FBO LLC
ClearCompany Sale to Gemspring Capital Management
Volery Capital Management Sale to Sustainable Development Capital
Digital Virgo Business Combination with Goal Acquisitions Corp.
5E Advanced Materials, Inc. Convertible Notes PIPE Offering
SunCap Acquisition of Adventure Forest, LLC
Prime Number Acquisition I Corp. Closes IPO
TradeStation Announces Business Combination with Quantum FinTech
Battery Future Acquisition Corp. Closes US$345M IPO
Citadel Defense Co.'s Acquisition by BlueHalo
View All Related Matters

Credentials

Education

Olga received her B.A. from Illinois State University. She earned her J.D. magna cum laude, from the University of Illinois College of Law.

    Admissions
    • California
    • Illinois

    Related Insights & News

    Olga is a prolific writer, speaker, and moderator on topics related to tax and SBIC programs, and is regularly quoted in the press. Recent speaking engagements include:

    • “Qualified Small Business Stock, Carried Interest Tax Planning and Other Tax Considerations for PE Funds,” 2020 NY SBIC CFO Fund Conference (January 22, 2020)
    • “78th Institute on Federal Taxation,” NYU Institute on Federal Taxation (October 20-25, 2019, November 10-15, 2019)
    • “Tax Considerations for Private Equity Funds,” 2019 SBIC Fund Conference (June 17-18, 2019)

    • “Guaranteed Payments IRC 199A Reguations: Maximizing QBI Benefits,” American Bar Association Tax Meeting (May 9-11, 2019)

    • “Guaranteed Payments Under IRC 199A Regulations: Year-End Strategies to Maximize QBI Benefits,” Strafford webinar, (December 3, 2018)

    • “Tax Considerations for Private Equity Funds,” 2018 SBIC Fund Conference (June 18-19, 2018)

    • “Implications of the Tax Reform for Private Equity Funds,” PE CFO Roundable Conference (November 8, 2018)

    • “Tax Reform Implications - A Practical Guide for General Partners,” SBIA Western Private Equity Conference (April 18, 2018)

     

    Sponsorship
    Winston & Strawn Sponsors SBIA’s 2025 Midwest Deal Summit

    May 28, 2025

    Recognitions
    Winston Partners Featured on the Lawdragon 500 Leading Global Tax Lawyers List 2025

    May 19, 2025

    Sponsorship
    Winston & Strawn Sponsors SBIA’s 2025 West Coast Capital Summit

    March 25, 2025

    Speaking Engagement
    Winston Sponsors, Franklin Shen Speaks at ABA 2025 Midyear Tax Meeting

    February 19, 2025

    Sponsorship
    Winston & Strawn Sponsors SBIA’s 2025 Southern Private Equity Conference

    February 13, 2025

    Recognitions
    Winston Partners Recognized on the 2025 Lawdragon 500 Leading Dealmakers in America List

    October 22, 2024

    Article
    Winston Attorneys Author “Alternative Funds 2024 — USA” Chambers Global Practice Guide

    October 17, 2024

    Seminar/CLE
    Chicago SBIC Fund Reception & Conference

    June 24, 2024

    Client Alert
    The Supreme Court Strengthens Congress’s Taxing Power in Upholding the Mandatory Repatriation Tax

    June 24, 2024

    Recognitions
    Winston & Strawn Recognized in The Legal 500 U.S. 2024

    June 12, 2024

    Recognitions
    Winston & Strawn Recognized in Chambers USA 2024

    June 6, 2024

    Seminar/CLE
    Winston & Strawn Co-Hosted the Annual SBIC Fund Conference with RSM US LLP

    January 22, 2024

    View All Insights & News

    Capabilities

    Transactions
    Private Investment Funds
    Mergers & Acquisitions
    Private Equity
    Tax
    Secondaries & Liquidity Solutions
    Financial Services
    Cryptocurrencies, Digital Assets & Blockchain Technology
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