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About me

Short Profile:

Benjamin Hillard, Esq., is an attorney with a JD/MBA, a former investment banker, licensed real estate broker, licensed title agent and former appraiser.  Ben has worked with Mortgage Data Management Corp., Goldman Sachs, Lehman Brothers, Morgan Stanley, Ocwen Financial, Countrywide, Wachovia and Washington Mutual.  While employed at Ocwen Financial, Ben purchased assets from the FDIC, RTC and SBA.


Extended Profile:

Benjamin Hillard Esquire is an attorney at Hillard & Rogers, P.A. ("Hillard | Rogers").  Ben conducts business litigation, real estate and corporate law litigation, mergers and acquisitions (M&A), business purchases and sales, banking, wills, trusts and probate.


Ben is also the president of Hillard Consulting Group, Inc., a firm that conducts commercial and residential loan purchase due diligence, acquisitions advisory, and loan sale advisory services, mergers and acquisitions ("M&A") due diligence, business plan review and development, commercial loan and real estate acquisitions, commercial loan underwriting, site inspections, and document review.  Ben has conducted consulting work, either directly or through Mortgage Data Management Corporation, for Goldman Sachs, Lehman Brothers, Morgan Stanley, Ocwen Financial, Countrywide, Wachovia, and Washington Mutual. 


During the late 1990s, Ben worked as an analyst, senior analyst and manager at Ocwen Financial Corporation.  While at Ocwen, Ben had primary responsibility for, or participated in acquisitions transactions ranging from $2 million to $195 million.  Ben also conducted all aspects of commercial asset acquisitions including: deal selection, underwriting, leveraged asset pricing, credit committee presentations, litigation review, negotiating purchase and sale agreements for sub-investment grade commercial asset acquisitions including loans, commercial real estate and bankruptcy claims.  Several notable include asset purchases from Wells Fargo, Federal Deposit Insurance Corp. (“FDIC”), Resolution Trust Corp. (“RTC”) and the Small Business Administration (“SBA”).  Ben’s first wholly managed transaction [$19 million] resulted in a net gain of more than $2.1 million at greater than 90% ROE.  Ben has conducted individual asset underwriting and overall project cash flow analysis for CMBS and CLO transactions.  Ben completed Ocwen's management development program that included formal training in banking, negotiating and supervisory skills.


Prior to joining Ocwen's acquisitions group, Ben was responsible for a portfolio of up to 700 mortgage foreclosures in 15 states by managing more than 60 outside counsel attorneys; making legal counsel hiring and firing decisions, and litigation management.


Benjamin Hillard is licensed to practice in Florida and in the Middle District Federal Courts.   Ben also maintains are Florida Real Estate Broker's License and Title License.  Ben is a former licensed Florida Appraiser. 


Benjamin Hillard earned an MBA from the Stetson University School of Business and a Juris Doctor degree from the Stetson University School of Law that focused on mergers and acquisitions, corporate bankruptcy, and corporate restructuring.  Ben also has an undergraduate business degree from Palm Beach Atlantic University. 


What sets Ben apart is the diversity of his background.  As a former banker, Ben knows how to negotiate and litigate against the banks.  He has developed a value-event-driven investment strategy that has achieved average annual gains in excess of 64% the 6.5 year period beginning in 1999.   Benjamin Hillard's article, "Judgment Liens on Real Property: Recent Decision Causes Uncertainty for Title Companies, Bankers, and Lawyers", was published in the Florida Bar Journal in February 2008.    Ben is a former semi-professional beach volleyball player including a  "men's open" wins at the Maryland Invitational and a second place finish at the University of Florida.


Photos and videos

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Practice areas


  1. Foreclosure: 80%
    9 years, 225 cases
  2. Real Estate: 10%
    11 years, 15 cases
  3. Business: 10%
    11 years, 15 cases



Hourly ($275/hour), contingent (30-40%), Fixed (sometimes)

Payment types:

Cash, Check, Credit card

Attorney endorsements

2 total 

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  • Christian K. Lassen II

    Top-notch attorney. Highly respected in the legal community.


    Christian Lassen Personal Injury Attorney
    Relationship: Fellow lawyer in community

  • Amanda Hope Meadows

    Ben is a very knowledgeable attorney with a skill set above and beyond most practitioners in his area. He uses his extensive background in banking and finance to the strong advantage of his clients. I have referred several clients to Ben, knowing that they will be in very good hands.


    Amanda Meadows Social Security Attorney
    Relationship: Fellow lawyer in community

Contact info

Hillard Law Group P.A.

13143 66Th Street North
Largo, FL, 33773



FLMember in Good Standing200409/08/2015
We have not found any instances of professional misconduct for this lawyer.
Avvo contributions
Legal answers
Work experience
TitleCompany nameDuration
El PresidenteCastle Law Group PA2008 - Present
PresidentHillard Law Group P.A.2007 - Present
ConsultantMortgage Data Management Corporation2004 - 2006
PresidentHillard Consulting Group, Inc.2001 - 2012
Analyst/Sr.Analyst/ManagerOcwen Financial Corporation1997 - 2001
Legal CoordinatorOcwen Financial Corporation1996 - 1997
Association namePosition nameDuration
Mid-Pinellas Chamber of CommerceN/A2010 - Present
The BoardN/A2009 - Present
Florida BarN/A2004 - Present
School nameMajorDegreeGraduated
Stetson University College of LawLaw & MBAJD/MBA - Juris Doctorate and MBA2004
Palm Beach Atlantic UniversityBusiness ManagementBS - Bachelor of Science1996
Speaking engagements
Conference nameTitleDate
Continuing EducationHow the Financial & Banking Crisis Impacts Florida Real Estate2011