Benjamin E. Hillard, Esq., MBA

Former Banker Turned Foreclosure Defense Attorney

Ben is a former banker turned trial lawyer that conducts business and real estate litigation including defending commercial and residential foreclosure suits.

Ben’s Unique Banking Background

Before becoming a foreclosure defense attorney, Ben spent the bulk of his professional career as mortgage banker and professional loan buyer, purchasing mortgage loans from other banks. Ben’s prior banking career also included managing hundreds of foreclosure cases on behalf of Ocwen Financial. Ben’s unique banking background makes him an undeniable authority, well-prepared to render advice and to litigate mortgage loan issues.

During his former career as a banker, Ben conducted loan purchase due diligence on tens of billions of dollars of loan purchase transactions. He has worked for Ocwen, Lehman Brothers, Goldman Sachs, Countrywide, Wells Fargo and many other institutional lenders. More specifically, Ben conducted loan purchase due diligence, negotiated loan purchase and sale contracts, and developed loan purchase pricing and bidding strategies. In Ben’s loan acquisitions consulting practice, he was often hired by the buyer bank to review loan files to determine if the seller bank actually followed their own lending standards. Finally, Ben has been through Countrywide’s forensic loan fraud training.

Additionally, Ben maintains a Florida real estate broker’s license and is a former Florida licensed real estate appraiser and former title agent. He has a multi-perspective understanding of mortgage loan issue resolution; including short sale, deed in lieu, foreclosure, and strategic default – and how to work all angles when preparing a strategic foreclosure defense.

Because of his unique banking background, Ben has a keen understanding of how banks make decisions on upside-down loans, the financial and banking crisis, lending standards and deviations from sound lending standards, and how these factors impact foreclosure defense in Florida.

Ben is also available to be booked for speaking engagements where he speaks on the financial and banking crisis and how lenders view upside-down loans. He has been the featured speaker at the Pinellas Realtor Organization (“PRO”), the Greater Tampa Association of Realtors (“GTAR”), the Mid-Pinellas Chamber of Commerce, The Board Tampa Bay and at a number of other organizations.

Outside of the office, Ben’s interests are as well-rounded as his background. He’s an avid fisherman, a disciplined weight trainer, a ballroom dancer, chess aficionado, and a former semi-professional beach volleyball player.

Relevant Professional Experience


Castle Law Group, P.A.
Managing Shareholder | May 2008 – Current
  • Foreclosure Defense Attorney; typically with the litigation goal of avoiding a deficiency judgment
Hillard Law Group, P.A. f/k/a Hillard& Rogers, P.A.
Managing Shareholder | August 2007 – Current
  • Business litigation including: real estate, title, banking, foreclosure, corporate law, Mergers & Acquisitions (M&A), and shareholder derivative suits.

Hillard, Cuykendall & Allred, P.A.
Managing Shareholder | August 2014 – Current

  • Business litigation including: real estate, title, banking, foreclosure, corporate law, Mergers & Acquisitions (M&A), and shareholder derivative suits.

Hillard Consulting Group, Inc.
President | Feb. 2001 – current

  • Commercial and Residential loan purchase due diligence, acquisitions advisory, and loan sale advisory services
  • Commercial loan and real estate acquisitions, commercial loan underwriting, site inspections and document review
  • Conducted due diligence and consulting work for Goldman, Lehman, Morgan, Countrywide, Wachovia, & others
  • Example: due diligence & consulting regarding asset pricing strategies for a $1.2 billion SBA loan purchase transaction

Hillard Law Firm LLP
Partner | April 2006 – July 2007

  • Business and real estate litigation, Corporate and real estate law


Mortgage Data Management Corporation (MDMC)
Consultant | December 2004 – April 2006

  • Loan purchase and Mortgage-backed securities (“MBS”) purchase due diligence and analysis including: credit and collateral underwriting and review, state & federal legal compliance review of loan documents 

U.S. Bankruptcy Court, Tampa Division
Federal Judicial Internship, Intern/Law Clerk | Fall 2003 

  • Legal research and drafting memoranda in both substantive and procedural bankruptcy law


Ocwen Financial Corporation, (NYSE: OCN)
Analyst, Sr. Analyst & Manager; Commercial Acquisitions Group | September 1997 – Jan 2001

  • Review and analysis of billions of dollars of mortgage loans for purchase from other banks, the FDIC, the RTC and the SBA. Conducted purchase & sale agreement negotiations for commercial loan and commercial asset acquisitions

Ocwen Financial Corporation, (NYSE: OCN)
Legal Coordinator, Legal Department | May 1996-September 1997

  • Management of more than 60 “outside counsel” attorneys over a portfolio of up to 700 mortgage foreclosures in 15 states.

Full Resumé and Recommendations

Licenses & Admissions

  • Florida Bar
  • U.S. District Court, Middle District Federal
  • Florida Real Estate Broker
  • Former Licensed Florida Title Agent
  • Former Florida Appraiser


  • Stetson University School of Business, MBA
  • Stetson University College of Law, Juris Doctor, Emphasis on Mergers & Acquisitions, Corporate Bankruptcy and Corporate Restructuring
  • Palm Beach Atlantic College, B.S. Business Management, Cum Laude



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