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For more than a decade Mr. Winters has been providing strategic and legal advice to airlines and aviation related companies around the world.Mr. Winters has been elected by shareholders to serve on the Board of Directors of multiple airlines and airline holding companies.His breadth of knowledge, strategic theories and practical experience have led him to senior executive roles at several international airlines.In addition to serving as a United States commercial and legal advisor for one of the largest airlines in South America, Mr. Winters has held senior executive roles at several airlines in the United States with both passenger and cargo carriers.Mr. Winters’ reputation for creative strategies to lower operating costs, develop organic growth opportunities and attract new lines of revenue, have made him a highly sought after aviation consultant.

Throughout his career he has orchestrated and documented countless Wet and Dry Lease Programs throughout the World and enjoys an excellent reputation with Lessors, Lenders and Lessees, alike.Mr. Winters has led exploratory teams conducting due diligence on target acquisitions and has been responsible for several corporate acquisitions including the purchase of a Canadian Cargo Airline and a highly complex debt restructuring andfleet acquisition involving a syndicate of the world’s top lenders.

Mr. Winters has authored several Restructuring Plans for various airlines around the world and currently serves as a commercial advisor for a sophisticated start-up airline in the United States.

Although Mr. Winters is an attorney and economist by education, his practical experience and reputation for integrity throughout the aviation community has enabled him to hold various positions at a host of aviation related companies, including President and Chief Executive Officer.

Work experience

Memberships and Admissions
  • Member of the Bar for the State of Florida and the U.S. Virgin Islands
  • Membership pending to the Federal Bar for the Commonwealth of Puerto Rico
  • Admitted to practice before the State Courts of Florida, the Territorial Courts of the U.S. Virgin Islands, the U.S. 11th Circuit Court for the Southern District of Florida and the U.S. 3rd Circuit Court for the U.S. Virgin Islands
  • Member of the Caribbean Bar Association and Florida Bar Business Law Section
Nov 2007Present

Founder - Partner

Winters & Waite, LLC
  • Established multi-jurisdictional law firm specializing in international aviation matters and commercial transactions
  • Advisor to International and Domestic Start-up Airline operations
Mar 2006Oct 2007

Vice President - General Counsel

Ryan International Airlines, Inc. - Rubloff Aviation
  • Recruited by shareholders to assist non-industry CEO with operations and management of over fifteen (15) privately held aviation/travel related holdings, including: Ryan International Airlines, Inc., a U.S. Certificated Part 121 International Passenger Airline, Rubloff Jet Express, Inc., a U.S. Certificated Indirect Air Carrier, RD Air, LLC., a U.S. Certificated Part 135 Charter Operation, Sundowner Airlines, a Charterer providing repatriation airlift to the U.S. Marshals Service and Immigration Naturalization Service, Branson Ticket and Travel, a travel/tour company, Jet-X Aerospace, Inc., an international aircraft parts supply company, and multiple special purpose entities designated for the ownership of aircraft
  • Served as Senior Executive for Ryan International Airlines operating 30+ Aircraft serving 22 countries around the World with 650 employees, two Labor Unions and annual revenues in excess of $225M
  • Responsible for negotiating and documenting all agreements on behalf of the Companies; including aircraft and aviation asset sales and leasing, maintenance agreements, service agreements, Supplemental Type Certificate engineering agreements, marketing agreements, charter agreements, wet/dry lease agreements and government service agreements
  • Developed key relationships to reduce third party costs and further business development objectives with Customers
  • Negotiated and documented arrangements for Aircraft Management Programs, for both domestic and foreign Aircraft
  • Significant experience acquiring/selling/managing aviation assets, including operational and maintenance obligations
  • Managed outside Representatives and Vendors around the globe on behalf of all aviation related holdings to ensure efficient and timely results at or below projected costs
  • Negotiate and document settlements of various claims including insurance settlements up to total aircraft losses
  • Responsible for operational and legal oversight of various programs; including, domestic and foreign Charter/Wet Lease Operations, Charter Procurements for the U.S. Department of Defense, U.S. Marshals Service, Civil Reserve Aircraft Fleet (CRAF), Department of Homeland Security and integration of foreign registered seasonal Aircraft and crews
  • Led the relocation of Ryan International Airlines’ Corporate Headquarters and displacement of 250 employees
  • Developed staffing strategies for increased use and efficiency of Independent Contractors
  • Served as the final authority and lead strategist for all disputes involving the Company, both internal and external
  • Represented the Companies before the EEOC, Union Grievance Committee and other governing bodies
  • Established Legal Department and positioned Ryan International Airlines for a private equity offering within 18 months
Jan 2002Jun 2005

Vice President - General Counsel

TradeWinds Airlines
  • Established and led the Legal Department for an International Cargo Airline with revenues in excess of $100 million
  • Spearheaded series of acquisitions and organic growth objectives that tripled earnings during tenure
  • Consummated acquisitions of a Canadian Cargo Airline and TradeWinds’ fleet of eight (8) A300 Aircraft
  • Helped raise and document over $30M dollars in syndicated financing to facilitate acquisition of Aircraft fleet
  • Managed internal employee relations with ultimate accountability for the Global Human Resources Department
  • Corporate Spokesman and Representative handling public relations and speaking engagements
  • Negotiated with foreign authorities to become the first privately held U.S. cargo airline to operate flights intra-Asia
  • Managed exploratory teams to assess risks and open markets in Asia, Latin America and the Caribbean
  • Negotiated and drafted all agreements with the Company, including, but not limited to asset sales/leasing, service agreements, customer agreements, employment agreements, confidentiality agreements and real property agreements
  • Monitored and controlled all outside representation and corporate agencies on behalf of the Company
  • Developed a proactive approach to protect and defend the Company from legal threats
  • Elected by shareholders to serve as Director and Corporate Secretary on the Board of Directors
  • Managed Shareholder Relations for Coreolis Holdings, Inc., the penultimate owner of TradeWinds Airlines, Inc.
  • Procured and administered Insurance Policies, including Hull and Asset Liability, Workers Comp. and D/O
Feb 1998Jan 2002


Jarvis & Associates, P.A.
  • Boutique aviation law firm specializing in full-service representation for aviation related clients
  • Responsible for documenting multiple aviation related transactions representing buyers, sellers and lenders
  • Served as outside Chief Collections Counsel for prominent Miami based International Cargo Airline
  • Civil claims experience in both Florida State and Federal Courts
  • Workload allocation: 80%|10%|10%; transactional, litigation and regulatory; respectively
  • Employed fulltime while pursing Juris Doctorate degree in Executive Degree Program

Senior Aviation Attorney


Summer Study Program (2 Semesters)

University of the West Indies

Specialized international exchange program emphasizing cross-boarder transactions, offshore investing, immigration, international commercial dispute resolution, foreign business structures and derivatives of Common Law.

Aug 1997May 2000

Juris Doctorate Degree

University of Miami - School of Law

International and Comparative Law Review

Executive Degree Program (Evening/Summer Classes)

Aug 1993Apr 1997

Bachelors of Science Degree

University of Florida Men’s Crew Team