The Massaro

Legal Group, LLC

Boutique Litigation Law Firm Focusing on Business, Contract, Commercial, and Real Estate

The Massaro Legal Group, based in the metro Indianapolis, Indiana area, brings almost 30 years of hands-on litigation experience. We have helped clients navigate disputes in complex business, commercial, contract, and real estate litigations. Whether it’s negotiating agreements or handling litigation, we’re here to offer customized solutions to your particular business and real estate litigation needs.

Meet Jason M. Massaro

Jason Massaro’s nearly 30 years of litigation experience and entrepreneurial spirit have shaped his dynamic approach to legal consulting. From his early career in complex litigation to founding and growing a successful boutique law firm, Jason has developed a reputation for strategic thinking, client commitment, and delivering exceptional results. In addition to The Massaro Legal Group, Jason has taken his deep understanding of Indiana’s legal landscape and passion for mentoring others, and now leads The Office Down the Hall (“ODH Legal Consulting”) where Jason offers Indiana lawyers and law firms unparalleled guidance in litigation strategy and business consulting.

Explore each tab to discover Jason’s experience, background, and accomplishments.

Jason M. Massaro is the owner of The Massaro Legal Group in Indianapolis, Indiana, where he focuses his practice primarily on complex business, commercial, contract, and real estate litigation. His experience ranges from counseling individuals as well as businesses of all sizes ranging from small to Fortune 500 companies in a variety of matters including litigation, contract issues, real estate matters, closely-held and minority shareholder disputes, Limited Liability Company (LLC) and partnership disputes, negotiations, corporate and partnership structuring, and corporate compliance. These litigations vary but often involve claims pertaining to fiduciary duty matters, member and shareholder claims, member, director, and officer liability, day-to-day business disputes, fraud, restrictive covenants (such as non-compete, non-solicitation, confidentiality, and nondisclosure agreements), trade secret violations, Indiana Securities Act violations, and real estate disputes, as well as general business counseling.

Jason is also the owner of The Office Down the Hall (“ODH”). ODH offers litigation strategy, business consulting, motion practice and discovery solutions, and culture and client retention guidance. ODH’s mission is to be a trusted partner to empower Indiana attorneys and law firms compete at the highest level by providing comprehensive litigation strategy and business consulting services designed to enhance operational efficiency, drive business growth and profitability, and ensure legal compliance, so they can deliver exceptional legal services to their clients.

Jason has been in practice for almost 30 years and is consistently recognized for both his legal ability and ethics. He has earned an AV® Distinguished™ Peer Review Rating from Martindale-Hubbell®, is listed as a Super Lawyer® Top Rated Business Litigation Lawyer, is a Fellow in the Litigation Counsel of America, and is also listed as one of Indiana’s Top-Rated Lawyers.

Jason is also active in various Indiana bar associations where he has served as an Executive Committee Member, Litigation Section, Indiana State Bar Association (ISBA); Executive Committee Member, Business Law Section, ISBA; Executive Committee Member, GP, Solo, and Small Firm Section, ISBA; Chair, ISBA Litigation Section; Chair, ISBA GP, Solo, and Small Firm Section; Executive Committee Member, Defense Counsel of Indiana (DTCI); Chair, Trial Tactics Section, DTCI; and Chair, Business Litigation Section, DTCI. Jason is also a Distinguished Fellow in the Indianapolis Bar Foundation, a Master in the Indianapolis American Inn of Court, and a Member of the Fishers Rotary Club. He was the recipient of the Civility Award, Outstanding Civility and Professionalism in the Courtroom, from the ISBA and often serves as a speaker and panel member for various Indiana continuing legal education seminars.

Valparaiso University School of Law, J.D., Magna Cum Laude, 1996.

Purdue University, B.S, with distinction, Economics, Krannert School of Management, 1993.

  • Minor, U.S. History, focus on 20th century military conflicts
  • Minor, Psychology
  • Minor, Spanish

BAR ADMISSIONS

Indiana Supreme Court
U.S. District Court, Northern District of Indiana
U.S. District Court, Southern District of Indiana

  • AV® Distinguished™ Peer Review Rating from Martindale-Hubbell®
  • Super Lawyer® Top Rated Business Litigation Lawyer
  • Fellow in the Litigation Counsel of America
  • Listed as one of Indiana’s Top-Rated Lawyers
  • Executive Committee Member, Litigation Section, Indiana State Bar Association (ISBA)
  • Executive Committee Member, Business Law Section, ISBA
  • Executive Committee Member, GP, Solo, and Small Firm Section, ISBA
  • Chair, ISBA Litigation Section
  • Chair, ISBA GP, Solo, and Small Firm Section
  • Civility Award, Outstanding Civility and Professionalism in the Courtroom, ISBA
  • Executive Committee Member, Defense Counsel of Indiana (DTCI)
  • Chair, Trial Tactics Section, DTCI
  • Chair, Business Litigation Section, DTCI
  • Distinguished Fellow, Indianapolis Bar Foundation
  • Master, Indianapolis American Inn of Court
  • Member, Fishers Rotary Club
  • Speaker and Panel Member, Various Indiana Continuing Legal Education Seminars
  • Executive Committee Member, Hamilton County Habitat for Humanity

In his spare time, Jason is a “foodie” who enjoys cooking and grilling for his family and friends. Jason loves to be outdoors, swim, and watch good movies and documentaries.  Jason’s competitive nature drew him to train as a wrestler.  He also studied for over fifteen years earning black belts in practical survival fighting and combat techniques.  Jason is an avid follower of US military history and the advocacy and protection of our veterans and all military personnel who made the ultimate sacrifice. Jason is an ardent patriot who is passionate about the protection of all personal liberties and freedoms. He is an accomplished tactical shooter and has trained with several top tier shooters including attending the Sig Sauer Academy in Epping, New Hampshire.

Download Jason’s vCard

Jason M. Massaro is the owner of The Massaro Legal Group in Indianapolis, Indiana, where he focuses his practice primarily on complex business, commercial, contract, and real estate litigation. His experience ranges from counseling individuals as well as businesses of all sizes ranging from small to Fortune 500 companies in a variety of matters including litigation, contract issues, real estate matters, closely-held and minority shareholder disputes, Limited Liability Company (LLC) and partnership disputes, negotiations, corporate and partnership structuring, and corporate compliance. These litigations vary but often involve claims pertaining to trade secret violations, fraud, securities act violations, fiduciary duty, and real estate disputes.

Jason is also the owner of The Office Down the Hall (“ODH”). ODH offers litigation strategy, business consulting, motion practice and discovery solutions, and culture and client retention guidance. ODH’s mission is to be a trusted partner to empower Indiana attorneys and law firms compete at the highest level by providing comprehensive litigation strategy and business consulting services designed to enhance operational efficiency, drive business growth and profitability, and ensure legal compliance, so they can deliver exceptional legal services to their clients.

Jason has been in practice for almost 30 years and is consistently recognized for both his legal ability and ethics. He has earned an AV® Distinguished™ Peer Review Rating from Martindale-Hubbell®, is listed as a Super Lawyer® Top Rated Business Litigation Lawyer, is a Fellow in the Litigation Counsel of America, and is also listed as one of Indiana’s Top-Rated Lawyers.

Jason is also active in various Indiana bar associations where he has served as an Executive Committee Member, Litigation Section, Indiana State Bar Association (ISBA); Executive Committee Member, Business Law Section, ISBA; Executive Committee Member, GP, Solo, and Small Firm Section, ISBA; Chair, ISBA Litigation Section; Chair, ISBA GP, Solo, and Small Firm Section; Executive Committee Member, Defense Counsel of Indiana (DTCI); Chair, Trial Tactics Section, DTCI; and Chair, Business Litigation Section, DTCI. Jason is also a Distinguished Fellow in the Indianapolis Bar Foundation, a Master in the Indianapolis American Inn of Court, and a Member of the Fishers Rotary Club. He was the recipient of the Civility Award, Outstanding Civility and Professionalism in the Courtroom, from the ISBA and often serves as a speaker and panel member for various Indiana continuing legal education seminars.

Jason received his B.S, with distinction, in Economics from the Krannert School of Management at Purdue University and his J.D., magna cum laude, from Valparaiso University School of Law.

Valparaiso University School of Law, J.D., Magna Cum Laude, 1996.

Purdue University, B.S, with distinction, Economics, Krannert School of Management, 1993.

  • Minor, U.S. History, focus on 20th century military conflicts
  • Minor, Psychology
  • Minor, Spanish

BAR ADMISSIONS

Indiana Supreme Court
U.S. District Court, Northern District of Indiana
U.S. District Court, Southern District of Indiana

  • AV® Distinguished™ Peer Review Rating from Martindale-Hubbell®
  • Super Lawyer® Top Rated Business Litigation Lawyer
  • Fellow in the Litigation Counsel of America
  • Listed as one of Indiana’s Top-Rated Lawyers
  • Executive Committee Member, Litigation Section, Indiana State Bar Association (ISBA)
  • Executive Committee Member, Business Law Section, ISBA
  • Executive Committee Member, GP, Solo, and Small Firm Section, ISBA
  • Chair, ISBA Litigation Section
  • Chair, ISBA GP, Solo, and Small Firm Section
  • Civility Award, Outstanding Civility and Professionalism in the Courtroom, ISBA
  • Executive Committee Member, Defense Counsel of Indiana (DTCI)
  • Chair, Trial Tactics Section, DTCI
  • Chair, Business Litigation Section, DTCI
  • Distinguished Fellow, Indianapolis Bar Foundation
  • Master, Indianapolis American Inn of Court
  • Member, Fishers Rotary Club
  • Speaker and Panel Member, Various Indiana Continuing Legal Education Seminars
  • Executive Committee Member, Hamilton County Habitat for Humanity

In his spare time, Jason is a “foodie” who enjoys cooking and grilling for his family and friends. Jason loves to be outdoors, swim, and watch good movies and documentaries.  Jason’s competitive nature drew him to train as a wrestler.  He also studied for over fifteen years earning black belts in practical survival fighting and combat techniques.  Jason is an avid follower of US military history and the advocacy and protection of our veterans and all military personnel who made the ultimate sacrifice. Jason is an ardent patriot who is passionate about the protection of all personal liberties and freedoms. He is an accomplished tactical shooter and has trained with several top tier shooters including attending the Sig Sauer Academy in Epping, New Hampshire.

Litigation Strategy and Business Consulting

At The Massaro Legal Group, in greater Indianapolis, attorney Jason Massaro has extensive experience in issues involving business litigation and consulting. Jason is also experienced in real estate litigation and other legal disputes involving real property whether it is residential, commercial, or industrial.

Business Litigation

At The Massaro Legal Group, we understand how serious the consequences can be when there is a legal dispute between businesses, or between businesses and individuals, that arise from commercial or contractual matters. Often, litigation is the only recourse.

Real Estate Litigation

At The Massaro Legal Group, attorney Jason Massaro litigates legal disputes related to real property ownership, contractual transactions, and rights, by resolving conflicts that could affect property values, ownership, and the overall functioning of the real estate market.

Legal and Business Consulting

At The Office Down the Hall (“ODH Legal Consulting”), attorney Jason Massaro provides a collaborative partnership with Indiana lawyers personalized to your particular, complex litigation needs as well as the refinement of your business practices designed to achieve optimal results.

The Office Down the Hall Litigation Strategy and Business Consulting

The Office Down the Hall Litigation Strategy and Business Consulting

Indiana’s Trusted Partner For Litigation Strategy and Business Consulting

In addition to our legal services at The Massaro Legal Group, Jason Massaro has opened The Office Down the Hall (“ODH Legal Consulting”). ODH Legal Consulting provides innovative solutions designed to empower Indiana lawyers and law firms with the tools, strategies, and insights they need to succeed in and out of the courtroom. With nearly 30 years of experience, attorney Jason Massaro offers support in:

  • Comprehensive pre-trial planning to develop effective legal approaches.
  • Case assessment to identify strengths and weaknesses in your case for optimal positioning.
  • Pleading development.
  • Discovery formation.
  • Motion practice, argument development and presentation.
  • Case theme development.
  • Witness identification and preparation.
  • Evidence assessment, marshalling, and presentation.
  • Alternative dispute resolution.
  • Expert retention.
  • Voir dire/jury selection.
  • Opening and closing arguments.
  • Direct and cross-examination.
  • In-trial consulting.
  • Post-trial strategy and briefing.

  • Developing precise discovery plans to gather essential evidence.
  • Case and issue assessment to decide most valuable evidence and information.
  • Gathering evidence to support claims, affirmative defenses, weaknesses in the opposing case, foster settlement, and prepare for trial.
  • Document management.
  • Effective discovery use to identifying key witnesses including fact and expert witnesses, witness preparation, and adverse witness examinations.
  • Discovery disputes including motions to compel and motions for protective orders.
  • Understanding and leveraging technology including E-discovery.
  • Maximizing discovery effectiveness, efficiency, and proportionality.

  • Streamlining operations to improve efficiency and profitability.
  • Implementing best practices for case management and client relations, billing, marketing, and overall internal management.
  • Detailed file management, organization, and structure.
  • Means to consistently display preparedness and organization.
  • Training attorneys and staff on workflow optimization and service delivery.
  • Development of trusted advisors.

  • Building a strong, client-focused firm culture.
  • Enhancing communication strategies for better client engagement.
  • Improving client interaction, client satisfaction and long-term retention rates.
  • Developing a positive work environment as well as the general atmosphere of the firm.
  • Delineation and incorporation of your firm’s overall values, ethics, and principles emphasizing integrity, respect, and professionalism.
  • Developing work-life balance, your own, and your employees’ emotional and mental well-being.
  • Fostering mentoring programs, continuing education, and opportunities for advancement.

Through our combined legal and consulting expertise, we help Indiana lawyers and law firms tackle challenges with clarity and confidence.

Visit the Site to Learn More Today!

In addition to our legal services at The Massaro Legal Group, Jason Massaro has opened The Office Down the Hall (“ODH Legal Consulting”). ODH Legal Consulting provides innovative solutions designed to empower Indiana lawyers and law firms with the tools, strategies, and insights they need to succeed in and out of the courtroom. With nearly 30 years of experience, attorney Jason Massaro offers support in:

  • Comprehensive pre-trial planning to develop effective legal approaches.
  • Case assessment to identify strengths and weaknesses in your case for optimal positioning.
  • Pleading development.
  • Discovery formation.
  • Motion practice, argument development and presentation.
  • Case theme development.
  • Witness identification and preparation.
  • Evidence assessment, marshalling, and presentation.
  • Alternative dispute resolution.
  • Expert retention.
  • Voir dire/jury selection.
  • Opening and closing arguments.
  • Direct and cross-examination.
  • In-trial consulting.
  • Post-trial strategy and briefing.

  • Developing precise discovery plans to gather essential evidence.
  • Case and issue assessment to decide most valuable evidence and information.
  • Gathering evidence to support claims, affirmative defenses, weaknesses in the opposing case, foster settlement, and prepare for trial.
  • Document management.
  • Effective discovery use to identifying key witnesses including fact and expert witnesses, witness preparation, and adverse witness examinations.
  • Discovery disputes including motions to compel and motions for protective orders.
  • Understanding and leveraging technology including E-discovery.
  • Maximizing discovery effectiveness, efficiency, and proportionality.

  • Streamlining operations to improve efficiency and profitability.
  • Implementing best practices for case management and client relations, billing, marketing, and overall internal management.
  • Detailed file management, organization, and structure.
  • Means to consistently display preparedness and organization.
  • Training attorneys and staff on workflow optimization and service delivery.
  • Development of trusted advisors.

  • Building a strong, client-focused firm culture.
  • Enhancing communication strategies for better client engagement.
  • Improving client interaction, client satisfaction and long-term retention rates.
  • Developing a positive work environment as well as the general atmosphere of the firm.
  • Delineation and incorporation of your firm’s overall values, ethics, and principles emphasizing integrity, respect, and professionalism.
  • Developing work-life balance, your own, and your employees’ emotional and mental well-being.
  • Fostering mentoring programs, continuing education, and opportunities for advancement.

Testimonials

When you are involved in a legal dispute, poor service and/or communication from your attorney can make the experience almost unbearable. That is why we go to great lengths to ensure that our reputation for service is of exceptional quality. Read testimonials below from both clients and other lawyers with whom we have worked who have firsthand experience with our outstanding services!

As a client, Jason made it seem that my best interests were all that mattered. Jason was initially retained to formulate a new business entity for myself so that I could further develop and grow in my professional field. That meant the development of business plans, agreements, and other contracts. As time passed, other personal needs of mine arose, which included more complex litigation matters involving banking, financing, and real estate issues. All of those needs were met with the utmost of professionalism and persistence to achieve the desired goal. Jason is someone I trust implicitly with all my business and personal matters. However, something that struck me the most was Jason’s ability to use the law to achieve a just result as opposed to ever lowering himself to tactics which would compromise his integrity and ethical standards. His stance on these issues made me trust him even more.

Often you add people to a board of any non-profit in hopes that they will contribute something more…it is not often that you get to see someone really enhance a board of directors once they join. Jason Massaro is an asset to the mission work of Habitat for Humanity. His interaction is not egocentric, but heart driven. His obvious talent of the English word and good humor make it a joy to work with him.

I have known Jason now for nearly 13 years. In that time, I have grown to respect his intellect, his work ethic, and his abilities. Jason was one of the outstanding graduates from law school. He had great ability to understand and analyze complex legal issues. In addition, he has always had the personal conviction to hold his ground. I would highly recommend Jason. In particular, I believe him to be uniquely suited for any complex legal matter involving litigation.

Jason is an excellent attorney and mentor. He was always willing to provide assistance and guidance. Jason led by example and he was always able to demonstrate the most effective ways to research, write and argue various legal issues. Jason is very dedicated to the practice of law and to his clients. I consider myself lucky that I was able to work with him and have him as a role model.

I had occasion to work with Jason on a complex real estate litigation matter. The matter was set for a two (2) week jury trial. Given the circumstances, my firm and I were brought in at the latter part of the litigation to assist. Upon review of the file, it became very clear that Jason had developed a thorough litigation strategy, lucid evidentiary presentation, and had prepared the file efficiently and effectively. Moreover, Jason had a highly organized and detailed approach to file management despite the tremendously voluminous amount of data and documents. In addition, Jason was always aggressively timely in his responsiveness to any question and/or request my office had. Jason is thorough, diligent, and detail oriented and I respect his litigation skills.

I have worked with Jason for over ten (10) years both as co-defense counsel and as an adversary. Jason is prepared, amenable, thorough and ethical. I think Jason works hard and carefully to balance the traditional challenges of litigation: results, cost and demeanor. Jason is a capable litigator, and I recommend him.

Jason and I went to law school together and I have had the pleasure of working with him since. Both in school and as a practicing lawyer, I can state that Jason works hard for his clients. If a good deal is to be made for his client, he will find it. If, on the other hand, litigation is needed Jason will take care of business on that end as well. His work ethic and his ethics are of the highest order.

Jason is an exceptional legal advisor and we’ve enjoyed our relationship with him and his team. I respect Jason’s honest and straight forward approach and would recommend his services without reservation.

Jason Massaro has a passion, drive, and understanding of the law that makes him a wonderful asset to have in your corner. He has honed his skill and presence in the legal field though many endeavors and participatory venues. Jason gives his clients no less than his best, in striving for the outcome they desire. I’ve had the pleasure of speaking with Mr. Massaro both professionally and personally and I’m always impressed with his deportment. To work with someone who is both professional and pleasant, makes for progressive interaction. It is with confidence that I write this letter of recommendation for Mr. Massaro, and would be happy to recommend him to my associates and clients.

In my 26 years of practice, I have met and worked with many attorneys. Jason Massaro routinely exhibits the highest level of skill, professionalism and integrity in every aspect of his practice. In addition, his trial advocacy skills are superior in every respect.

I’ve known Jason for at least 15 years. Since then, we have worked together on cases, and we frequently consult with each other on questions of our respective areas of expertise. Jason has a considerable amount of experience in business and other litigation and extensive knowledge of business law. He knows as much or more about trial procedure than any other lawyer I can think of. Jason is thoroughly familiar with statutes and case law relevant to small businesses, as well as the rules of trial procedure and appellate procedure. In addition to being familiar with the law, he can apply it to real life situations. Jason’s demeanor and work product meet the high standards of professionalism. I recommend him for litigation and particularly business litigation.

Jason Massaro has proven to be knowledgeable, responsive, and very helpful when consulted about multi-state and international legal matters, and also provided pragmatic and simple business counselling, and swift contract review and resulting recommendations.

Jason is an excellent trial lawyer who I have worked with several times in the past. Most recently, I hired Jason for my business litigation matter. Jason’s preparation and attention to detail are impeccable. Jason is obviously experienced and skilled in the courtroom and his ability to present complex issues in an understandable way was the key to our success. I highly recommend Jason for anything to do with litigation or trial work.

Jason did a fantastic job! My wife and I were very pleased from the very beginning. Mr. Massaro was very knowledgeable and explained things in a manner we could understand. Our issue was resolved within a matter of weeks. If we ever need another attorney, we will certainly use him again.

From the first phone call to the resolution of my issue, I was treated with kindness and professionalism. I had never needed legal services before and hope to not in the near future. But if I do, I will for sure call him. Thanks Jason!

We have used Jason for many years, and multiple instances, and have been very satisfied. We have used several law firms in the past, and have always been disappointed with availability, pricing, and more. I have never felt that way with Massaro. Jason gets things done, and takes time to always give me sound advice, and he is very easy to get a hold of. Not usually the case in that industry. I think they are the best in the area.

Our experience with Jason was outstanding. From the moment we made the consultation appointment for a real estate matter we felt very comfortable, and when we met Jason for our initial consultation, we knew right away we made the right choice! Jason was attentive to our needs, conscientious and compassionate. Very thorough counsel and when we left the office, we knew we had the right team representing us – that’s a great feeling!

Jason is a great communicators and listens to his clients, unlike many other attorneys. I appreciate his professionalism and advice on a multitude of different legal topics.

I’ve known Jason for twenty years, and in my opinion, he is truly one of the best business litigation attorneys in Indianapolis.

Jason is very sharp and knowledgeable. He is an attorney I often reach out to in a tough legal situation to gain his insight on an issue.

Contact Us

While this website provides general information, it does not constitute legal advice. The best way to get guidance on your specific legal issue is to contact a lawyer. To schedule a meeting with an attorney, please email JMassaro@TMLGlaw.com or complete the intake form.

Our Info

  • Our Location:
    154 W. Carmel Dr.
    Suite 230
    Carmel, IN 46032

  • Mailing Address:
    12409 E 256th St.
    Cicero, IN 46034

  • Office Hours:
    Weekdays: 9:00 am to 5:00 pm EST
    Weekends: CLOSED

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