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Overview

Simon Crawford is shortlisted by every major Canadian and international legal guide, including Chambers Global, Canadian Legal Lexpert Directory, Euromoney Expert Guide and Best Lawyers in Canada, as one of Canada's leading real estate lawyers, and is listed in the 2018 Lexpert ALM 500 comprehensive guide to Canada’s top legal talent, as one of the 500 most frequently recommended lawyers across Canada, in any ranked discipline, as determined by annual peer survey. Simon was recently accepted as a Fellow for ACMA (American College of Mortgage Attorneys). 

He is among a small handful of lawyers in Canada who are called upon regularly to lead and structure the country’s largest and most complex real estate bids and transactions, and has been a key advisor and strategist in developing, trading, financing, and tailoring the ownership and joint venture structures for many of the country's landmark office, commercial, retail, sports and entertainment, infrastructure and residential projects and portfolios.

In 2017, Simon was the lead advisor on transactions valued in excess of $4 Billion, including the acquisition of approximately $1.2 Billion in commercial mortgages from Home Capital/Home Trust. In 2016 he was the lead advisor in connection with the acquisition of one of Toronto’s landmark skyscrapers, Scotia Plaza. In 2015, he was the lead real estate advisor to a significant landlord group in connection with the insolvency proceedings related to Target Canada, the largest Canadian retail insolvency in recent history. Simon was featured in the September 2014 issue of Lexpert magazine as lead counsel to a consortium in respect of 2013's largest commercial real estate transaction, the acquisition of all Primaris Real Estate Investment Trust properties. In 2012 he acted as counsel to the purchaser of a $2 Billion industrial real estate portfolio comprised of more than 400 properties.

Simon advises many of Canada's most sophisticated real estate investors on private equity matters, fund formation, joint ventures, income trusts, the purchase and sale of real estate assets and real estate companies, property development, banking and mortgage lending, structured finance and asset securitization, corporate finance, mezzanine and participating debt structures, infrastructure, public/private partnerships, mortgage and loan servicing and enforcement, and on real estate issues in bankruptcy and insolvency.

In recent years, Simon has acted as senior advisor on some of Toronto’s more notable new developments and financings, including Cumberland Terrace, the Bay-Adelaide Centre, the Trump Tower, and the 75-storey Aura condominium project, which is currently the tallest residential building in Canada. Across the country, Simon has also acted on large portfolio transactions, including the acquisition and financing of ING's industrial portfolio and the privatization of both Atlas Cold Storage and Versacold.

Complementing Simon's real estate practice is extensive deal experience in public/private partnerships, the creation of pension-fund eligible investments, and the financing and trade of regulated facilities such as gaming, infrastructure healthcare and long-term care projects. In addition, Simon has acted for government or quasi-government interests, including most notably, as advisor to Waterfront Toronto in connection with the development of Toronto's waterfront lands.

Simon has represented clients in the financing or sale of a significant number of Canada's landmark office, commercial, entertainment and retail properties, including Toronto's 2 Bloor and Cumberland Terrace, Bay Adelaide Center, Trump Tower, Primaris Shopping Centre portfolio, Scotia Plaza, Brookfield Place, TD Centre and First Canadian Place, Montreal's Eaton Centre, Ottawa's Rideau Centre, Saskatchewan's Midtown Plaza and Calgary's Scotia Plaza and Palliser Square. Simon has also represented lenders or purchasers in connection with various sports and recreation facilities including in connection with the 2010 Olympic games, Toronto's Ricoh Centre and Niagara Falls Casino.

Simon is called upon regularly to moderate panels for the commercial real estate community, is a prolific writer and speaker on developments in real estate law, is a frequent lecturer for the Law Society of Upper Canada for the continuing education of the real estate bar.

Client Work

Freed Developments Ltd. in its approximately $330-million acquisition of a portfolio of real property assets of including Horseshoe Valley Resort, Deerhurst Resort and some additional lands from Skyline Investments, together with the purchase of the portion of Muskoka Bay Resort it did not already own.
KingSett in the purchase from the Huntley group of a portfolio of industrial properties located in the GTA. 
KingSett in the sale of its 100% interest in the first three floors of the Aura Tower, located at 388 Yonge Street in downtown Toronto, to the Ikea group of companies.
Lead Real Estate Counsel to a significant landlord group, in the Target Canada insolvency.
December 02, 2015 - Lead Counsel to Canderel and KingSett Real Estate Growth LP No. 5, in the acquisition of 1243 Islington Avenue, Toronto,, a 107,824 square foot office building located at Islington Avenue and Bloor Street West, Toronto. http://www.marketwired.com/press-release/canderel-kingsett-capital-venture-into-west-end-office-market-2078726.htm
November 18, 2015 – Lead Counsel to KingSett Canadian Real Estate Income Fund LP and its partner, in its acquisition of 2 Bloor Street West, a 455,371 square foot, 34-storey Class A office tower located at Yonge & Bloor, Toronto.

Recognitions & Awards

Chambers Canada

Ranked, Real Estate
Ranked, Real Estate – Ontario

Chambers Global The World's Leading Lawyers for Business

Ranked, Canada, Real Estate


The Legal 500 Canada

Leading Lawyer, Real Estate

Canadian Legal Lexpert Directory

Most Frequently Recommended, Property Development
Consistently Recommended, Property Leasing
Repeatedly Recommended, Environmental, Social & Governance ESG
 

 

 

Lexpert/American Lawyer Guide to the Leading 500 Lawyers in Canada

Ranked, Property Development

Lexpert Special Edition

Recognized as a leading Infrastructure lawyer in Canada

Education & Bar Admissions

Education

  • University of Toronto, BA, 1994, with honours
  • Osgoode Hall Law School, LLB, 1997

Bar Admissions

  • Ontario, 1999

News, Events & Speaking Engagements

PlaceholderSpeaking Engagement

Buyer (Counsel) Beware of an Apportionment of Damages

April 9, 2025
Simon P. Crawford
Simon P. Crawford
PlaceholderSpeaking Engagement

The Eight-Minute Real Estate Lawyer 2024

November 19, 2024
Simon P. CrawfordCraig R. R. Garbe
Simon P. Crawford & Craig R. R. Garbe
PlaceholderSpeaking Engagement

Simon Crawford at LSO's 18th Annual Real Estate Law Summit

April 19, 2021
Simon P. Crawford
Simon P. Crawford