Richard G. Douglass



Richard G. Douglass is a partner at Novack and Macey LLP where he represents individuals and businesses of all sizes in complex commercial litigation disputes related to finance, insurance, real estate and professional liability. Rich is also co-chair of the firm’s Legal Malpractice Defense group, successfully representing attorneys and law firms against breach of fiduciary duty and other claims. Throughout his career, Rich has earned high praise for his legal ability and professionalism. 

First and foremost, Rich fights hard for his clients, and works diligently to provide the best possible representation to his clients.  As a result, he has earned his clients’ trust and respect.  Clients have praised Rich for, among other things:

“adeptness at developing creative legal arguments and suggesting innovative solutions;”

“impressive ability to digest very complicated facts and issues, and then communicate them with efficiency and ease;” 

presenting “creative and thoughtful options that improved our argument and positioning of the case at every stage of the process;”

displaying “excellent judgment and great strategic instincts;”

providing “insightful counsel grounded in a thorough understanding of a complicated business”

“quick thinking and ability to anticipate issues and challenges before they presented themselves;”

“tireless efforts and genuine enthusiasm;” and

“the utmost in professionalism and integrity, [which] reflects well on his firm and the legal community.”

Likewise, Rich has earned praise from his colleagues, co-counsel and, notably, his adversaries.  In fact, one former opposing counsel had this to say:  “[During our case] Mr. Douglass performed at a high-level and garnered my respect as a fellow lawyer.  Mr. Douglass is the type of lawyer you enjoy litigating against because he always comes prepared and ready to fight for his clients but does so while being professional.”

Rich’s work has garnered public recognition as well.  He has been ranked AV® Preeminent by the Martindale-Hubbell Lawyer Ratings Service.  He has been named as an Illinois Super Lawyer every year since 2015 by Super Lawyers magazine. This accolade is reserved for no more than 5% of all attorneys in Illinois.  And, he was selected as one of the “40 under Forty” most talented young attorneys in Illinois in 2013 by the Chicago Law Bulletin.   

When not working, Rich spends his time with his wife and daughter in Elmhurst, Illinois. Rich is an avid car enthusiast (both shows and racing), a mediocre golfer, and a periodic gamer.  Rich grew up in Wheaton, Illinois, went to college at the University of Pittsburgh, and obtained his law degree from the University of Georgia, in Athens. Before joining Novack and Macey, Rich was at Fortson, Bentley and Griffin, PA, in Athens and worked in their litigation and commercial transactions departments.  


  • University of Pittsburgh (B.A. 1998), Magna Cum Laude
  • University of Georgia School of Law (J.D. 2002), Magna Cum Laude, Order of the Coif; University of Georgia Law Review, articles editor

Representative Cases


  • Representing multi-billion dollar U.S. regional banking corporation in contract and tort claims arising out of loans to a life insurance premium finance business and related entities, including private equity backers.
  •  Representing individual directors of national construction company in dispute with shareholders over $100 million plus proposed transaction. 
  • Representing national enterprise information management services company in dispute with former customer over service agreements originally made with business acquired by the current client.
  • Representing an insurance broker in a dispute with a national insurance company regarding the issuer’s refusal to perform under the terms of a agreement to market and sell hundreds of millions of dollars worth of insurance.
  • Represented regional bank in multiple disputes involving third party disputes over the ownership of accounts, including competing claims raised in probate court.
  • Represented multiple law firms in disputes brought by third parties over the services provided by those firms to their clients.
  • Represented international Bitcoin exchange and related entities in a class action alleging fraud arising out of the failure of the exchange and other contractual disputes related to financial services.
  • Represented regional financial services/telecommunications firm in dispute with national cellular service provider over threatened disruption of long-term service agreements.
  • Represented a provider of employee assistance programs in connection in a suit against a former, high-level employee in claims arising under restrictive covenants when he went to work with a competitor.
  • Represented a packaging manufacturing company in asserting claims arising from the unlawful termination of the company’s distribution agreement with its primary distributor.
  • Represented a global diamond and jewelry company in connection with the theft of a diamond ring and the resulting dispute with the company where the stolen ring was pawned, which claimed a superior security interest in the ring. 
  • Represented an engineered materials company in connection with a breach of trade dress lawsuit against a competitor.  
  • Represented a provider of employee assistance programs in a dispute concerning a breach of contract by one of the provider’s international customers. 
  • Represented one of the largest privately-owned manufacturing companies in defending multi-million dollar claims brought by one of its global customers. 
  • Represented a Chicago law firm in a suit against a federal agency for unpaid legal fees, costs and expenses. 
  • Represented a global equipment rental company in pursuing claims against a customer that had failed to pay millions in rental and related fees and expenses. 
  • Represented officers and directors of a computer technology company in defending claims brought under the Securities Laws related to a private offering of stock.
  • Represented consumer electrical product company in connection with a dispute over an engagement agreement with its terminated patent counsel. 
  • Represented former guarantor in defending claims brought by a lender seeking to collect on the guaranty.
  • Frequently retained as local counsel in various matters, including in putative class actions against medical device manufactures, pet food manufactures and sellers, insurers and financial service providers.


  • Representing ex-CEO of regional artisan coffee company who successfully revamped the business ahead of its acquisition by a national coffee chain in a dispute between the CEO and the company regarding the non-payment of compensation and bonuses, including, among other things, those due upon the successful sale.  
  • Representing executive who was retained by an online merchant to reinvigorate the company and position it for sale in a dispute between the executive and the company regarding his purported termination and the company’s refusal to pay compensation and bonuses.  
  • Representing and represented several high-level financial advisors and traders in disputes with former employers regarding unpaid salary, commission and bonuses and/or related to equity and profits rights. 
  • Represented employers, employees, partners and shareholders in multiple disputes concerning the alleged violation of restrictive covenants in connection with employment and sale of business agreements.  
  • Represented an energy company in multiple actions concerning disputes over participant rights under an SEC-registered long term incentive program.


  • Represented real estate investor in several related disputes in multiple jurisdictions concerning a luxury residential development located in Hawaii.  
  • Represented multiple clients, including individuals and real estate investment partnerships, in tort and contract-based claims arising out of real estate purchase and lease agreements.
  • Represented a North Suburban Chicago real-estate developer in a series of lawsuits arising out of several developments on the North Shore of Chicago.  
  • Represented a large Chicago-based mixed-use developer in defending claims for breach of warranty, fraud and breach of fiduciary duty brought by the board of directors of the residential condominium association.
  • Represented a real-estate developer in connection with a claim for breach of contract by a potential project lender.
  • Represented a real-estate developer in connection with a dispute with its supplier and the supplier’s bonding company in a claim regarding delayed deliveries of supplies.
  • Represented potential purchaser of real estate in defending a suit by the seller seeking specific performance of contract for purchase and sale.
  • Represented owner of retail parcel in mixed-use building in code compliance action brought by City of Chicago involving extensive disputes among owners of the various mixed-use parcels.
  • Represented the residential condominium association in a mixed-used building in several related lawsuits asserting their claims against the owner/manager of the commercial portion of the building.
  • Represented owner and manager of a retail shopping mall in defending against a foreclosure action instituted by its lender.
  • Represented a real estate development company in defending against related foreclosure actions against various properties located throughout the Midwest.
  • Represented residential owner of townhome in dispute with homeowners’ association regarding covenant violations and breach of fiduciary duty claims. 
  • Represented foreclosing lenders in multiple foreclosure actions, including taking properties through foreclosure to sale and negotiating and closing short sales.


  • Represented PJM Interconnection in connection with federal court claims, including RICO claims, against a group of participants based on alleged market manipulation.
  • Represented a national energy company in connection with a dispute regarding its acquisition of a demand response aggregation business concerning alleged breaches of representations in a stock purchase agreement.
  • Represented national energy derivatives trading company in connection with alleged breach of a long-term power purchase agreement in connection with disputes arising as a result of the implementation of locational marginal pricing in ISO New England.
  • Represented Illinois alternative retail electricity supplier in disputes with commercial and industrial customers over power purchase agreements.
  • Represented a national retail natural gas supplier in disputes with commercial and industrial customers over long term gas purchase agreements.
  • Represented a limited partner in an oil and gas exploration and production partnership in connection with breach of fiduciary duty claims against the general partner.