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,
  • issuance of credit enhancements in bond transactions,
  • 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
  • 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 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.
  • Manufacturing business with a stock acquisition by an international purchaser, negotiating the stock purchase agreement, ancillary transaction documents, and advising the client regarding export control regulations related to “ITAR” and “CFIUS”.
  • 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 in numerous transactions
  • 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
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