Sr. Management Bios

James Callahan

Jim Callahan is the principal of Pentalpha Global Advisors. Founded in the early 1990's, Pentalpha is considered an industry-leading workout firm dedicated to repairing damaged financial institutions and the debt instruments they issue. The firm is staffed with former investment banking and finance company traders, bankers, quantitative analysts and operations specialists with loan origination and loan collections expertise. The firm specializes in European and US interests.

In the 1998 Russian debt crisis as well as the 2008 mortgage “meltdown”, Pentalpha was hired to play a leading advisory, daily management role or damage analytics role in some of the largest failures and restructurings in the history of the financial services industry. Assignments effecting hundreds of billions of dollars of assets, millions of borrowers and thousands of employees are not uncommon. Collections optimization of debt instruments collateralized by real estate and consumer interests are a specialty. In many instances, Pentalpha’s divisional managers oversee financial institutions as they work out "high stakes" loans on a loan-by-loan basis while Mr. Callahan provides more of the strategic advisory services.

Long-term independence is Mr. Callahan’s and the firm’s most valuable attribute. To avoid conflicts, the firm does not take principal positions or originate/service loans that may be in competition with the client’s interests. As validation of Mr. Callahan’s and the firm’s commitment to independence, Bank trust departments have hired Pentalpha to act as co-trustee and distressed situation experts when the trustee has had conflicts themselves. Further, the firm has been hired to take leadership advisory roles in representing either Federal agencies, corporate office and boards, creditors or equity holders. While restructurings as well as mergers and acquisition resolutions are a strong preference in optimizing a stressed firm, Pentalpha has taken the senior role in liquidating financial services companies through the Federal bankruptcy process.

When the markets are more stable, Mr. Callahan is well known for devising new financing products. Some of his innovations are considered “break through” and included in the multi trillion dollar mortgage and corporate markets. Mr. Callahan has been an active advisor to Federal regulators on many matters including finance industry reform and optimizing the government’s holdings that it acquires when a regulated institution is placed into receivership or conservatorship.

Prior to founding Pentalpha, Mr. Callahan was a senior trader and banker on Wall Street with trading desk management responsibility for various domestic and international corporate, consumer and mortgage debt products. He was also part of the divisional risk management committee. Prior to being a trader, Mr. Callahan worked in the asset and liability management department of a top five bank where he helped manage the firm’s regulatory capital requirements and price international corporate loans to optimize the bank’s earnings. Mr. Callahan has served on the Board of various corporate trusts.

Mr. Callahan is an active leader in various not-for-profit organizations. As the senior officer or as a board member, Mr. Callahan has taken leadership roles in cultural, educational and amateur sporting organizations. Away from Pentalpha and not-for-profit interests, Mr. Callahan is an active collector of art-deco-style American pickup trucks, an avid fly fisherman and he is national champion in a class of racing sailboats. Mr. Callahan has three adult daughters.


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