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Jonathan M. Silverstein
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Attorney Jonathan Silverstein has 29 years of experience counseling clients on licensing, land use,
real estate, zoning, contracts and permitting.
Jonathan has represented clients in a broad range of cases, including land use, real estate, civil rights,
tort, contract and environmental, before all levels of the Massachusetts and Rhode Island trial courts,
the United States District Court (Districts of Massachusetts and Rhode Island), the Massachusetts
Appeals Court and Supreme Judicial Court, the Rhode Island Supreme Court, and the United States Court of Appeals for the First Circuit.

Jonathan also advises clients with respect to large-scale development and redevelopment projects,
including commercial projects as well as residential and mixed-use projects (under conventional
zoning as well as comprehensive permit projects under Chapter 40B and smart-growth projects
under Chapter 40R). He assists in the adoption of urban redevelopment plans, all aspects of land use permitting, negotiation of development and land disposition agreements, and related litigation.
Together with his partner Mark Bobrowski, Jonathan also assists municipalities with zoning
recodifications, as well as targeted zoning amendments including Chapter 40R smart-growth
districts, planned development districts and compliance with Chapter 40A, §3A (the so-called
MBTA Communities legislation). Jonathan has developed particular expertise in issues related to permitting, licensing and developing gaming establishments. He has represented clients across Massachusetts and New York in negotiating host community and development agreements as well as ancillary matters, such as establishment of redevelopment authorities, negotiation of urban redevelopment agreements, and large-scale rezoning efforts. Jonathan also regularly represents both municipal and private clients in matters relating to medical and adult-use marijuana businesses, including zoning, licensing and other permitting procedures, negotiation of host community agreements, and litigation. 
Representative Litigation Matters

Civil Rights/Tort
  • Freeman v. Town of Hudson, 714 F.3d 29 (1 st Cir. 2013). Federal Court of Appeals upheld
    dismissal of federal civil rights claims brought by developer against members of Town’s
    Police Department and Conservation Commission, claiming that his development activities
    were wrongfully scrutinized/regulated and that he was falsely arrested and criminally
    charged as a result of plaintiff’s dispute with his neighbor, who is also a member of the
    Town’s police department.

  • Grossi Development LLC v. Town of Rehoboth, U.S.D.C. 1:10-cv-10728-RWZ (Aug. 25,
    2011) (Zobel, J.), affirmed 1 st Cir. No. 2011-2365 (July 9, 2012). Federal District Court
    dismissed equal protection and due process claims by Chapter 40B developer, who claimed
    that Town’s Zoning Board of Appeals and Conservation Commission had interfered with
    ability to permit and construct residential housing development. The District Court’s
    judgment was affirmed by a panel of the United States Court of Appeals.


  • Rocheleau v. Town of Millbury, 115 F.Supp. 173 (D.Mass. 2000). Federal District Court
    awarded summary judgment to the Town and Town officials on various civil rights and tort
    claims against the Town and police officers, arising out of a pretrial detainee's alleged
    injuries while in a Town lock-up facility.

Comprehensive Permits/Enforcement
  • Town of Boxborough v. Boxborough Meadows, LLC. In the settlement of the first-ever
    action by a municipality to enforce the profit limitation imposed upon recipients of
    comprehensive permits for affordable housing projects under G.L. c.40B, the developer
    agreed to pay $1.2 million to the Town, to be used for affordable housing purposes.

Comprehensive Permits/Appeals
  • Marengi v. Salisbury Zoning Board of Appeals, 491 Mass. 19 (2022). In this case of first
    impression, the Supreme Judicial Court ruled that the bond provision of G.L. c.40A, §17 (3 rd
    par.) applies to appeals of comprehensive permits and secures expert witness fees and other
    litigation costs.

  •  DHL Associates v. Town of Tyngsborough, 64 Mass. App. Ct. 254 (2005). In a case of first
    impression, the Appeals Court held that Article 16 of the Massachusetts Declaration of
    Rights does not afford broader protections to adult entertainment than the First Amendment.

  • Jackson v. Town of Belchertown, 84 Mass. App. Ct. 1107 (2013). Appeals Court upheld
    dismissal of wrongful termination claim by former police lieutenant, who claimed his
    position was eliminated in retaliation for his participation in the investigation of a town
    official’s son.


  • City of New Bedford v. MCAD, 440 Mass. 450 (2003). SJC reversed MCAD's decision to
    affirm arbitration award in favor of police officer, who claimed that decision to remove him
    from City's SWAT teams was based upon unlawful handicap discrimination. In case of first impression, SJC adopted federal courts' definition of "handicap" in ADA cases for purposes of claims under G.L. c.151B.


  • Doe v. Superintendent of Schools of Stoughton, 437 Mass. 1 (2002). In the first case to
    interpret student-discipline provisions of G.L. c.71, §37H½ part of the Education Reform
    Act, the SJC upheld the decision of the Town's Superintendent of Schools to suspend a
    student charged with a felony that took place off school premises and during the summer
    break. This decision reaffirms the broad discretion of school officials with respect to student
    discipline and safety.

  • Town of Sturbridge v. Mobil Oil Company, U.S. District Court, C.A. No. 01-40019NMG.
    $1.6 million settlement in groundwater contamination action, pursuant to G.L. c.21E.

  •  Antonio v. City of Peabody, 51 Mass. App. Ct. 655 (2001), MLW June 4, 2001 (opinion
    digest). Appeals Court reversed denial of City's motion for summary judgment on grounds of inadequate presentment and ordered that judgment enter for the city.

Municipal Finance
  • Iacobucci v. Town of Amesbury, 77 Mass. App. Ct. 1109 (1:28 Decision), further appellate
    review denied, 458 Mass. 1104 (2010). Appeals Court held that debt authorization for
    capital expenditure (library renovation project) was not subject to referendum process under
    municipal charter. Court also held that plaintiffs’ Open Meeting Law claim and mandamus
    claim (seeking enforcement of various charter provisions) were properly dismissed.

Open Meeting Law
  •  Paicopolis v. Dartmouth School Committee, 72 Mass. App. Ct. 1117, further appellate
    review denied, 452 Mass. 1109 (2008). Appeals Court rejected a claim that the School
    Committee held improper executive sessions and also rejected a claim that the School
    Committee breached obligation of good faith and fair dealing with the public by considering
    various employment and contract matters in executive session.

Real Estate (Registered Land)
  • Town of Sandwich v. Panciocco, 48 Mass. App. Ct. 556, further appellate review denied, 431
    Mass. 1105 (2000). Appeals Court affirmed summary judgment for plaintiff Town in right-
    of-way case involving inconsistencies between confirmation plan of defendant's property and registration plan of plaintiff's property.

Real Estate (Right of Reverter)
  • Faneuil Investors Group v. Board of Selectmen of Dennis, 458 Mass. 1 (2010). Supreme
    Judicial Court held that Town could enforce right of reverter to void sale of municipal land to
    housing authority, based upon housing authority’s failure to obtain permission of selectmen
    prior to granting mortgage on property. Mortgagee/Bank claimed that mortgage was not
    “conveyance” sufficient to trigger reverter clause.

Sewer Connection
  • Lemansky v. Charlton Water & Sewer Commission, WOCV2004-01107 (2005). Summary
    Judgment rejecting the claim of property owners that they were improperly denied
    connections to municipal sewer for a large-scale development based upon a narrow strip of
    land connecting the development site to a public way in which municipal sewer line was
    located. Court also upheld sewer connection moratorium as valid exercise of Commission’s

Subdivision Control
  •  Wine v. Planning Board of Newburyport, 74 Mass. App. Ct. 521 (2009). Appeals Court
    upheld denial of definitive subdivision approval and rejected property owners’ claims that:
    (1) compliance with current subdivision rules and regulations was not required due to prior
    approval of subdivision plan for the same property; and (2) that the Planning Board’s denial
    of a waiver requirement for centerline offset was motivated by an improper attempt to
    prevent further subdivision of the property in question.

Subdivision Control/Damages
  • Arello v. Town of Auburn, WOCV2008-02542 (2009). Superior Court dismissed claims for
    damages and to remove cloud on title, arising from filing of conditions of subdivision
    approval approximately fifteen years after the original decision of Planning Board and seven
    years after the plaintiff purchased subject property.

  •  Arena v. Nantucket Planning Board, Appeals Court, 96 Mass. App. Ct. 1116, cert. denied
    484 Mass. 1103 (2020). Jonathan successfully defended the Nantucket Planning Board’s
    issuance of special permits for a 64-unit workforce housing development on Town-owned
    land, obtaining a summary judgment from the Land Court, which was affirmed by the
    Appeals Court.

  • Barkan v. Town of Truro, 95 Mass. App. Ct. 378 (2019) and Zehnder v. Town of Truro,
    Land Court No. 12 Misc. 459506 (2017). In this highly publicized zoning enforcement
    matter, Jonathan secured a settlement for the Town resulting in payments totaling $3 Million
    and successfully defended the settlement in subsequent litigation initiated by a group of

  • Kennard v. Zoning Board of Appeals of Eastham, 52 Mass. App. Ct. 1005 (2001), MLW July
    23, 2001 (opinion digest). Affirming judgment after trial upholding a decision of the Zoning
    Board of Appeals to deny plaintiff a special permit for the enlargement of a preexisting
    nonconforming structure and rejecting plaintiff's argument that denial of a special permit for “de minimis” enlargement was abuse of discretion.

  •  Lazarek v. Board of Appeals of Manchester-by-the-Sea, 95 Mass. App. Ct. 1105 (2019)
    (upholding Land Court dismissal of special permit appeal by abutter, based upon lack of

  •  Palitz v. Tisbury Zoning Board of Appeals, 470 Mass. 795 (2015).  In a case of first
    impression, the Supreme Judicial Court held that endorsement of an Approval Not Required
    (ANR) plan under the so-called “existing structures exemption” of the Subdivision Control
    Law does not protect the resultant lots from zoning enforcement, where the division of land
    results in new zoning nonconformities.

  •  Perotti-Cyrus v. Town of Sandwich, BACV2004-0767 (2009). After trial, Superior Court
    upheld a zoning enforcement order against the use of a cottage that was unlawfully sold into
    separate ownership from remaining cottages in a former seasonal cottage colony.

Prior Experience

KP Law, P.C. (previously Kopelman and Paige, P.C.), Boston, MA (1996-2022)
     Shareholder (2001-2022); Management Committee Member (2012-2022)
Rhode Island Supreme Court (1995-1996)
     Law Clerk, Justice Victoria Lederberg

Honors & Awards
  • Named a “Super Lawyer” in Municipal Law in the 2015-2023 editions of Super Lawyers

  •  Named a “Rising Star” in Municipal Law in the 2010 edition of Super Lawyers Magazine

  • Named one of five “Up and Coming Lawyers” by Massachusetts Lawyers Weekly in 2004

Bar & Court Admissions
  •  Massachusetts Bar

  • U.S. District Court (Mass.)

  • U.S. Court of Appeals for the First Circuit

  • Supreme Court of the United States

  • Boston College Law School
    Juris Doctor, 1995
    Editor, Environmental Affairs Law Review

  • Brandeis University
    Bachelor of Arts, cum laude, with High Honors, 1992


Representative Presentations
  • Survey of Significant Land Use Cases, MCLE: 25th Annual Environmental, Land Use & Energy Law Conference, Boston, MA, March 28, 2024

  • Cannabis Update, MCLE: 21st Annual Municipal Law Conference, Boston, MA, March 22,

  • Cannabis Update – Host Community Agreements, Delivery and Social Consumption,
    Massachusetts Municipal Lawyers Association Annual Conference, Taunton, MA, October
    14, 2022

  • Zoning Exemptions and Nonconformities, Southeastern Massachusetts Building Officials
    Association, Taunton, MA, January 2022

  • Adopting and Revising Rules and Regulations, Citizens Planner Training Collaborative,
    Virtual Presentation, December 2020

  • Special Permits and Variances, Citizen Planner Training Collaborative, West Newbury, MA,
    October 2019;
     Chelsea, MA, December 2019

  • Introduction to Subdivision Control, Citizen Planner Training Collaborative, Danvers, MA,
    June 2019; North Reading, MA, October 2018 & Brewster, MA, November 2017

  • Cannabis & Host Communities: What You Need to Know, Cannabis Society and Prince
    Lobel Tye LLP, March 2018

  • The Zoning Act and Municipal Control of Land Use, Middlesex County Town and City Clerks Association Annual Meeting, December 2017

  •  Zoning Exemptions, Citizen Planner Training Collaborative Annual Meeting, March 2017

  • Massachusetts Case Study—Host and Surrounding Community Agreements, National
    Conference of Legislators from Gaming States Annual Meeting, July 2016

  • Zoning Code Administration and Enforcement, Eastern States Building Officials Federation
    Annual Conference, Portsmouth, NH, April 2016

  • Exempt Uses Under the Massachusetts Zoning Act, Massachusetts Building Commissioners and Inspectors Association, July 2015

  • Hot Topics in Zoning Law, Boston Bar Association, May 2015

  • Casino Gaming, State Policy and Local Planning, Massachusetts Association of Planning
    Directors (MAPD), Westminster, MA, January 2014

  • Surrounding Communities Under the Massachusetts Gaming Act, Massachusetts Continuing
    Legal Education (MCLE), Boston, MA, December 2013

  • Massachusetts Gaming Law Update 2012, Massachusetts Continuing Legal Education
    (MCLE), Boston, MA, December 2012

  • Casino Coming to Town, Planning at a Crossroads, presented at the annual conference of the
    Southern New England Amer
    ican Planning Association (SNEAPA), Hartford, CT,
    September 2012

  • “Procurement Opportunities in the Gaming Sector: A Good Bet for those Who Play By the
    Rules,” Boston Bar Journal, Summer 2015

  • Comment: “Taking Wetlands to the Bank: The Role of Wetland Mitigation Banking in a
    Comprehensive Approach to Wetland Protection,” Boston College Environmental Affairs
    Law Review
    , Volume 22, Number 1

  • Author,” Lucas One Year Later: Merely a Footnote to the Regulatory Takings Doctrine,”
    National Environmental Enforcement Journal

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