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Timothy C Monahan.


Timothy C. Monahan



Tim Monahan focuses his practice in the arena of business and finance. With over ten years of experience, Tim has gained the knowledge and skill set to confidently assist clients in a varying range of issues. Tim represents lenders and borrowers in all types of financing transactions, including:

  • asset-based financing,
  • real estate financing,
  • general commercial financing,
  • construction financing,
  • participations, and
  • intercreditor transactions.

“I also advise clients in the merging, acquisition and sale of businesses, the formation of various entities, the structuring and negotiation of joint ventures,” and other general business contracts, such as loan documents. Additionally, Tim counsels businesses regarding regulatory compliance, contract interpretation, and securities filings.

Before Bowditch

Prior to joining Bowditch, Tim worked as an Associate at another law firm in Worcester.

Besides work

In addition to spending time with his family, Tim is an occasional runner (having completed the Boston and Marine Corps Marathons), golfer, and slow-pitch softball player. He also enjoys reading history in his spare time.


  • Member, Massachusetts Bar Association
  • Member, Boston Bar Association
  • Real Estate Finance Association (REFA), a division of the Greater Boston Real Estate Board (GBREB)


  • Former Member of Board of Directors, New England Hemophilia Association

Articles + Talks



Bar Admissions

  • Massachusetts
  • U.S. District of Massachusetts


  • J.D., Boston College Law School
  • B.A., cum laude, Boston College

Banking & Finance

  • Sale of stock for a supplier of machined and metalized ceramic substrates, which can be made to fit into sophisticated weapons systems used by the U.S. military and its allies; due to the military component and the fact that the purchaser is a foreign-owned company, we had to insure compliance with both International Traffic in Arms Regulations (“ITAR”) and obtain approval of the Committee on Foreign Investment in the United States (“CFIUS”), which reviews the national security implications of foreign investment. After about six months, working with the State Department, the Commerce Department, the client’s consultant and buyer’s counsel, we were able to obtain CFIUS approval, and a few weeks later, we closed the transaction for our client.
  • Sale of an insurance company for approximately $11 million dollars to a large national insurance provider, counseling the client on complex issues related to the asset sale, disclosures, employment issues, earnout and strategy.
  • Insurance benefits company in successful, multi-million dollar sale of its assets to a national insurance company; counseling the client on complex issues related to the asset sale, disclosures, employment issues and strategy.
  • Medical services company in the successful sale of one of its divisions; advised the client on complex issues related to liens and debt on certain assets, negotiation of all transaction documents and lease of certain property.
  • Commercial lender in the issuance of $1.5 million mortgage loan, helping the Lender to navigate a complex defeasance process related to the release of the primary security and deal with a federal agency that was long-term tenant in certain real estate.
  • Represented lenders and borrowers in commercial financing transactions involving asset-based real estate and construction financing
  • Counseled businesses regarding (and negotiated terms of) stock purchase and asset purchase agreements
  • Advised existing and start-up businesses related to entity formation, governance and the myriad of issues that arise in the day-to-day process of running a business
  • Represented a national bank in its provision and subsequent amendment of various lines of credit, including a $20 million dollar line of credit to be used exclusively in leveraged buyouts, to an international company in the business of providing premier obstacle course and endurance based sporting events.
  • Represented the lender in simultaneous transactions with related parties wherein the Lender loaned, via numerous lines of credit and multiple term loans, an amount totaling approximately $7 million dollars; approximately $5 million of the loan amount was in relation to a construction loan with a unique deal and collateral structure involving a guaranty from an unrelated tenant; the remaining $2 million dollars involved a straightforward formula based line of credit secured by an all asset lien; the transactions closed simultaneously as required.
  • Represented numerous lenders and borrowers in various financings involving interest rate swap agreements and loan amounts ranging from approximately $1 million to $9 million.


  • Represented a lender in a workout situation, negotiated forbearance agreement and additional security for the client.
  • Drafted ancillary documents for workout arrangements (notes, mortgages, other security instruments) on behalf of lender clients.




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