Lenny Asaro

Lenny is a partner in Taft’s Chicago Real Estate practice where he brings nearly three decades of experience advising clients on all facets of real estate development, land use, zoning, eminent domain, and litigation strategy. A trusted counselor and trial attorney, Lenny represents both public and private sector clients in high-stakes matters at the intersection of real estate, government, and community development. He brings a collaborative, client-first mindset and is deeply committed to delivering creative, forward-thinking solutions that drive successful outcomes for clients.

Lenny represents developers, municipalities, and institutions in securing zoning approvals, negotiating public-private partnerships, and litigating condemnation and real estate cases. His work spans site acquisition, entitlements, zoning and land use approvals, TIF financing, eminent domain, and real estate disputes. He values Taft’s collaborative model and cross-market leadership structure, which empowers him to deliver the full strength of Taft’s resources to clients in a nimble, efficient, and impactful manner. He serves as a strategic advisor to clients undertaking high-stakes development and redevelopment projects—often in politically sensitive or high-visibility contexts.

In line with Taft’s commitment to community impact, Lenny is passionate about civic engagement, pro bono service, and mentoring the next generation of legal talent. He embraces the opportunity to make a meaningful difference both in the courtroom and in the communities he serves.

Litigation/Trials

Eminent Domain

• City of Chicago: Served as Special Assistant Corporation Counsel and First Chair trial attorney from 1999 to 2021 on the acquisition of hundreds of properties spanning all asset classes (i.e., commercial, industrial, residential, mixed use, improved and vacant land). Responsibilities included developing project budgets, retaining consultants and experts, drafting ordinances, negotiating with owners and their legal counsel, closing on voluntary sales and managing all aspects of condemnation proceedings. Led the acquisition of properties under threat of condemnation via negotiation, purchase, and sale. Served as First Chair for multiple contested court hearings, bench trials and jury trials.
  • Blommer Chocolate Company Project: Served as First Chair trial attorney for two two-week jury trials. Highly contested acquisition of property from Fred Eychaner who was represented by an accomplished real estate litigation and eminent domain partner at a top five Am Law 50 international law firm. Developed and implemented the litigation and jury trial strategy to: (a) defeat challenges to the City’s exercise of the power of eminent domain at contested court and evidentiary hearings, (b) secure a jury verdict of just compensation favorable to the City; (c) support the City’s Appellate Division’s defeat of the owner’s appeal; (d) secure a second jury verdict of just compensation favorable to the City and (e) support the City’s Appellate Division’s defeat of the owner’s appeal to the Illinois Appellate Court, Illinois Supreme Court and United States Supreme Court.
  • Old Main Post Office: Served as lead attorney. Developed the legal strategy and worked closely with the Law Department and Commissioner of the Department of Planning and Development to implement the strategy to: (a) issue a request for proposals to select a developer to redevelop the dilapidated former post office and (b) draft and adopt an ordinance giving the City the power to exercise its power of eminent domain to acquire the property for redevelopment. Implementation of the strategy was the catalyst for the owner agreeing sell the property to New York-based 601W Companies who redeveloped and repositioned the property. Worked with 601W Companies on a consent decree arising out of housing court violations to ensure that the substantial deferred maintenance was remedied in a timely manner.
  • South Loop TIF (1011 S. State Street): Served as First Chair trial attorney on a one-week jury trial resulting in a favorable verdict of just compensation for the City of Chicago.
  • La Villita Park (S. Sacramento between 28th and 31st Streets): Served as First Chair trial attorney on a two-week jury trial resulting in a favorable verdict for the City. Owner’s attorney was an author of venerable treatise, Eminent Domain in Illinois. Acquisition of the 24-acre Superfund and former Celotex/Honeywell site that was remediated and redeveloped into a Chicago Park District park serving the South Lawndale community. The trial presented a unique legal issue whether evidence of the environmental condition of the property could be considered in arriving at a valuation of the property.
  • 15th and Michigan Ave.: Served as First Chair trial attorney. Then-Mayor Richard M. Daley specially assigned the matter to Lenny’s mentor Earl L. Neal who in turn selected Lenny to lead the acquisition of a blighted shopping center to facilitate redevelopment. After extensive discovery and pre-trial motions, the case settled on the first day of jury selection for just compensation favorable to the City of Chicago.
  • 75th and S. South Chicago Ave.: Served as lead attorney. Developed the land acquisition and zoning strategy and worked closely with the Law Department and Department of Planning and Development to implement the strategy to: (a) designate the area a Redevelopment Area under the City of Chicago Municipal Code, which at that time had not been done; (b) acquire hundreds of commercial, retail and residential vacant land parcels for the Gary Comer Science and Education Foundation Project which included a youth center, charter high school, charter middle school and public library. (See below).
• Kotara LLC and Braidkot, Ltd.: Served as lead counsel for Berkot’s Super Foods, a neighborhood, family-owned and operated, full-service grocery store company who owns and operates 16 stores throughout Illinois and Wisconsin. With respect to its store in Braidwood, Illinois, Lenny successfully defended the client on a partial taking by IDOT that caused economic and operational damage to the business, in particular its customer parking lot. Lenny zealously represented the client at the trial court and appellate court resulting in a published opinion in favor of the client, People ex rel.  Dept. of Transp. v. Kotara, L.L.C., 379 Ill. App. 3d 276, 884 N.E.2d 1235 (3d Dist. 2008).
• Public Building Commission of Chicago & Board of Education of the City of Chicago: Served as First Chair trial attorney and lead counsel on the acquisition of hundreds of parcels for the development of new police stations, fire stations and schools.
• Chicago Transit Authority:
  • Red Line/Fullerton/DePaul University: Served as lead counsel on the acquisition of property from DePaul University for the redevelopment of the Red Line Fullerton Station. Developed a professional relationship with opposing counsel who was a partner at an Am Law 100 law firm that resulted in multiple referrals by such partner over the ensuing decade, one of which is the referral of the DePaul University Basketball Practice and Training Facility Project. (See below Gary Comer Science and Education Foundation Project).
  • 95th Street Terminal Project: Served as lead counsel on the acquisition of property for the CTA and its 95th Street Terminal Expansion Project. Lenny successfully defended the CTA against a gas station-owner’s motion to dismiss and traverse the complaint by developing a legal strategy and assembling expert witnesses to defeat the owner’s claim that the full-taking was a temporary taking which would have derailed the entire project. Lenny implemented a strategy prior to and during the multi-day contested hearing with witness testimony, exhibits and legal briefs. Following the contested hearing, the trial court denied the owner’s traverse and motion to dismiss the complaint which allowed the CTA to move forward with the acquisition of the subject property and approximately 20 other adjacent properties to complete the project.
• McDonald’s Corporation:
  • Woodstock, Illinois: Represent McDonald’s on a partial taking by the Illinois Department of Transportation (“IDOT”) affecting access and relocation of business signage. Represent the company on obtaining zoning approvals for the remainder property as a result of the taking by IDOT.
  • Wisconsin: Provided advice and counsel to McDonald’s regarding a partial taking the Wisconsin Department of Transportation affecting the operation of the drive-through. o Zoning:
• NRG Energy/Midwest Generation: Successfully defeated the City of Waukegan’s effort to limit Midwest Generation’s use of its electricity generating facility located on Lake Michigan in the City of Waukegan. Without notice to the Midwest Generation, the City adopted an amendment to its Solid Waste Nuisance Ordinance to include the facility in the Lakefront Redevelopment Zone. Pursuant to the ordinance, Midwest Generation would be liable for removing the two coal ash ponds (i.e., solid waste impoundments) on site that have been in place since at least the 1970’s which would materially impact its land use rights given the 100+ year history of the site being used as a electricity generating facility. Lenny developed the legal strategy, based on case law, that the Solid Waste Nuisance Ordinance as applied to the subject property was tantamount to a zoning ordinance and, as such, the City violated Midwest Generation’s substantive and procedural due process rights by circumventing its Zoning Ordinance to effectuate a change in land use. Lenny secured a complete victory for Midwest Generation after the trial court granted Midwest Generation’s motion for summary judgment and denying the City’s cross-motion for summary judgment. During Lenny’s work on this real estate litigation matter, NRG retained Lenny to represent them on the development of part of the site into a battery energy storage system facility.
• Sky Zone: Successfully defeated a competing business from locating within close proximity to Sky Zone’s existing indoor trampoline park in Vernon Hills, Illinois. Sky Zone’s competitor sought to lease space in a shopping center within 1,200 feet of Sky Zone’s space. The competitor filed an application for special use permit. However, the application was substantively deficient and there were multiple procedural errors associated with the Village’s approval of the application. Lenny presented evidence, testimony, and legal arguments at the hearings before the Village’s reviewing body and Board of Trustees. Following the Village’s approval of the application, Lenny filed a complaint in Lake County Circuit Court to overturn the approval. After defeating the Village’s and competitor’s separate motions to dismiss the complaint, the competitor elected not to refile the application and, thus, abandoned the project.
• Williams Bay, Wisconsin: Represented owners of property located on Lake Geneva against their neighbors who claimed that the owners’ lakeshore line redevelopment and improvements violated zoning and other municipal regulations. Lenny developed the legal strategy that included working with the client’s general contractor to provide expert testimony. Lenny attended the hearing before the reviewing body and presented evidence, testimony, and legal arguments and cross examined the complainants which resulted in a denial of the claims and successful defense for the client.

Civil

• Data Centers: Represented an international data center operator resolve claims made by property owners.

Projects

• Gary Comer Science and Education Foundation:
  • Gary Comer Youth Center: Developed and led the acquisition strategy to acquire, rezone and develop the property at 7200 South Ingleside Avenue, Chicago, IL 60619 in the Greater Grand Crossing neighborhood into the Gary Comer Youth Center. Gary Comer, who was born on the South Side of Chicago in the Grand Crossing neighborhood and graduated from nearby Paul Revere Elementary School and went on to found Lands’ End, envisioned a multifaceted community development in the neighborhood in which he was raised. This project inspired the Revere Way, Greater Grand Crossing Library and Gary Comer College Prep High School projects.
  • Revere Way: Gary Comer envisioned the Gary Comer Youth Center as the hub and catalyst for a transformative neighborhood redevelopment that would include 75 single family homes known as the Revere Way project. Lenny helped develop the land acquisition strategy and led the implementation of the strategy to acquire more than 100 parcels of vacant and improved property in the southeast quadrant of 71st Street and S. Chicago Avenue via negotiation and eminent domain. Lenny served as Special Assistant Corporation Counsel for the City of Chicago to acquire parcels via eminent domain. Lenny negotiated the redevelopment agreement on behalf of the client to facilitate the acquisition via eminent domain. The acquisitions resulted in the construction of 55 single family homes paid for by Gary Comer, who in turn provided financial subsidies to the buyers.
  • Gary Comer College Prep: While the Revere Way Project was underway, Lenny was tasked with acquiring and rezoning the land adjacent to the Gary Comer Youth Center to develop the Gary Comer College Prep High School.
  • Greater Grand Crossing Library: Even though it was not part of the original project, during the successful implementation of the land acquisition, zoning and development of the youth center, single family homes and high school, Gary Comer foresaw the transformative opportunity to acquire a dilapidated motel located a few blocks away from the other project and donate the land to and partially fund the construction of a new public library for the City of Chicago. Lenny led the acquisition, rezoning, and development for this project.
• DePaul University Basketball Practice and Training Facility: Represented DePaul University on an amendment to a 54-acre planned development to pave the way for a new basketball training and practice facility at the northwest corner of Sheffield Avenue and Belden Avenue. The facility will be the university’s first team specific practice facility on the Lincoln Park campus. The new facility will feature an exterior, brick façade that mirrors the neighborhood, and a pitched roof that pays homage to DePaul’s former Lincoln Park arena, Alumni Hall. Floor-to-ceiling glass around the gyms will serve as a prominent focal point for recruits, showing off stunning views of where the Blue Demons call home — Chicago. Dedicated practice courts for each basketball program will greatly alleviate scheduling concerns, as all 15 of DePaul’s programs currently share the McGrath-Phillips Arena courts. The first floor of the facility will be dedicated to the health and wellness of all 215+ DePaul student-athletes, and will include a team dining space, nutrition bar, new sports medicine treatment spaces and offices, hydrotherapy, a weight room, and multi-purpose meeting rooms. Lenny negotiated with Ald. Knudsen and drafted a plan of operations agreement for the benefit of the community and neighborhood community organizations.
• National Mixed-Use Real Estate Developer: Represented a national mixed-use residential developer on an amendment to a planned development that was previously approved for a mixed use residential and ground floor retail in the Pilsen neighborhood of Chicago. The amendment paved the way for the first retail space to be developed and occupied.
• Esperanza Health Center: Represented Esperanza Health Center on the development of its second health center in the Bright Park neighborhood-Brighton Park South at 4720 S. California Avenue. This project is comprised of three dozen state-of-the-art exam rooms, full-service café, beautiful plaza, laboratory, meeting spaces, and more. Together with the already existing Brighton Park North located adjacent to Brighton Park South, the campus has become a leading destination for award-winning wellness and health services in the city. Lenny secured approval of the application for planned development and a related application for resubdivision.
• Chicago Southwest Development Corporation/Saint Anthony Hospital: Represent Chicago Southwest Development Corporation (“CSDC”) on the approximately 30-acre Focal Point Project at the southwest corner of 31st Street and Kedzie Avenue. Led by Saint Anthony Hospital’s former Chief Executive Officer, Guy Medaglia, the Focal Point Community Campus is a bold and visionary idea to provide Chicago’s vibrant west and southwest side communities greater opportunity to thrive while celebrating the diversity and rich history of its neighborhoods. Planned as a mixed-use community development anchored by Saint Anthony Hospital, Focal Point will be located on a previously a blighted tract of land and be home to a multi-use campus serving an area of over 440,000 people. Focal Point is a first-of-its-kind financially sustainable model based on rental income generated from campus tenants, ensuring a continuous flow of funds distributed into campus and surrounding neighborhood programs and services. Lenny handled the amendment to the planned development, acquisition of multiple parcels via negotiated purchase and sale and eminent domain, redevelopment agreement with the City of Chicago to purchase the former Washburne Trade School site which was the last parcel needed for the project. Lenny is working with the client on the next phases which include environmental remediation, construction, and project financing.
• Railroad Company: Represented a national passenger railroad company on a comprehensive redevelopment plan for its Chicago real estate assets.
• Chicago Fire Football Club: Represented the Chicago Fire Football Club of the MLS on its plan to secure shared site control over Hanson Park in the Belmont Cragin neighborhood to develop a practice facility and media/office for the MLS club. Lenny developed and implemented the land acquisition and zoning strategy which included negotiations with Ald. Gilbert Villegas, the Mayor’s Office, the Department of Planning and Development and Chicago Public Schools and drafting and negotiating a letter of intent and proposed community benefits. Lenny worked closely with the club’s real estate development team, which included ownership, Mansueto Office, and JLL.
• McDonald’s Corporation: Represented McDonald’s Corporation on applications for special use permits and variations for new restaurant sites and redevelopment of existing restaurant sites in the City of Chicago. Represented the company with respect to leasehold property tax matters and disputes related thereto involving restaurants at O’Hare Airport. Lenny’s advice and counsel resulted in substantial real estate tax savings for McDonald’s.
• Fifth Third Bank: Represented and continues to represent the bank on land use and zoning matters for bank branches located in the City of Chicago and suburbs.
• Steans Family Foundation: Represented and continues to represent the foundation on real estate development and acquisition matters involving property in the North Lawndale neighborhood where the foundation dedicates time, resources, and skills to revitalize the existing social, educational, and economic networks that create and sustain communities.
• Three Crowns Park: Represent Covenant Living Community and Services on the redevelopment of a landmark building known as Pioneer Place, which is part of the larger Three Crowns Park continuum of care retirement community in northwest Evanston, Illinois. Lenny leads on the application for a certificate of appropriateness and amendment to the planned development to renovate and activate the currently unoccupied Pioneer Place building.
• Hyde Park Day School/Sonia Shankman Orthogenic School: Represented two specialty schools on their plan to from the University of Chicago campus where both schools rented space from the university. Developed and implemented the site selection, land acquisition and zoning strategy to build a new dual school campus in the Woodlawn neighborhood on 63rd Street between S. Ellis and S. Ingleside. Negotiated a redevelopment and land purchase and sale agreement with the City of Chicago and negotiated a land purchase and sale agreements with private property owners. Secured zoning approvals for the project. Following completion of the project, Lenny accepted an invitation to join the board of the foundation who oversees the operation of the schools.
• Stonewater Master Development Project in Wonder Lake, Illinois: Represent the owner of a 1,400-acre proposed 3,700 residential unit master planned development regarding land disposition, zoning, litigation, and related matters.
• Advanced Power: Represented Boston-based international developer and manager of independent power generation and related infrastructure projects on a planned combined cycle electricity generating facility in Glenwood, Illinois. Developed and implemented strategy for site selection, acquisition, zoning, and real estate tax minimization.

Consulting/Lobbying

• Dollar Tree/Family Dollar: Represented the companies in their opposition to a City of Chicago alderman’s proposed amendment to the text of the Zoning Ordinance and Municipal Code that would limit the number of new stores the company could open in the City of Chicago. Worked with the client, Illinois Retail Merchants Association, the Chicagoland Chamber, and other stakeholders to lobby alderperson to oppose the proposed amendments. Developed legal strategy to rebut arguments in favor of the zoning text amendment. Served as the client’s spokesperson in an interview on WTTW.
• Life Care Services/The Clare at 55 E. Pearson, Chicago, IL: Represented national developer, owner, and operator of senior living continuum of care retirement communities regarding a City of Chicago Department of Finance audit of real estate taxes related to a complex transaction involving a recapitalization of the company.
• EverDriven formerly known as ALC Schools: EverDriven is the nation’s most trusted provider of innovative, safe student transportation and optimization solutions for school districts nationwide. Drafted a bill to amend the Illinois Vehicle Code and lobbied the Illinois Secretary of State, Illinois State Board of Education and General Assembly, working closing with Sen. Karina Villa. The catalyst for the bill was to create tailored driver’s license training and permitting procedures for First Division and Second Division vehicles used to transport students with unique needs to and from school to free up the Secretary of State’s backlog of applicants seeking school bus driver licenses. The bill passed and became law.
• Acquisitions/Dispositions/Leases: Drafted and negotiated a wide range of real estate contracts, including purchase and sale agreements, leases, license agreements, easements, and development agreements. Conducted due diligence reviews on property titles, zoning, environmental issues, and regulatory compliance for various real estate projects.