Background

Caplan grew up in Portsmouth, Virginia, and graduated from the Norfolk Academy

Norfolk Academy

Norfolk Academy is an independent co-educational day school in Norfolk, Virginia. Chartered in 1728, it is the oldest secondary school in Virginia and the eighth oldest in the United States...

 in 1975. He subsequently received a BA in history from Brandeis University

Brandeis University

Brandeis University is an American private research university with a liberal arts focus. It is located in the southwestern corner of Waltham, Massachusetts, nine miles west of Boston. The University has an enrollment of approximately 3,200 undergraduate and 2,100 graduate students. In 2011, it...

 – later receiving his JD and an MBA from Emory University

Emory University

Emory University is a private research university in metropolitan Atlanta, located in the Druid Hills section of unincorporated DeKalb County, Georgia, United States. The university was founded as Emory College in 1836 in Oxford, Georgia by a small group of Methodists and was named in honor of...

.

Caplan became involved with Juvenile Diabetes Research Foundation

Juvenile Diabetes Research Foundation

JDRF is the leading global organization focused on type 1 diabetes research. Driven by volunteers connected to children, adolescents, and adults with this disease, JDRF is the largest charitable supporter of T1D research...

, serving on its board, when one of his daughters (Ilana, 21) was diagnosed with diabetes. He has also served as a board member for the American Committee for the American Committee for the Weizmann Institute of Science (ACWIS)

Weizmann Institute of Science

The Weizmann Institute of Science , known as Machon Weizmann, is a university and research institute in Rehovot, Israel. It differs from other Israeli universities in that it offers only graduate and post-graduate studies in the sciences....

 and the Aspen Music Festival and School, as well as on the Corporate Fund Board of the Kennedy Center for the Performing Arts and as chairperson for Teach for America

Teach For America

Teach For America is an American non-profit organization that aims to eliminate educational inequity by enlisting the nation's most promising future leaders to teach for two or more years in low-income communities throughout the United States...

's Washington, DC advisory board.

Career

From 1984 to 1990 Caplan was an associate of the law firm Shearman & Sterling

Shearman & Sterling

Shearman & Sterling LLP is a law firm headquartered in New York City with 20 offices located in major financial centers around the world founded in 1873. It is well known for both its litigation and transactional capabilities, especially in International Arbitration, Capital Markets, Finance, and...

. Caplan served as vice-chairman and president of Telebanc Financial Corporation, a federally chartered savings bank, from January 1994. Caplan became CEO of Telebanc in 1998. E-Trade Financial acquired Telebanc in early 2000. The bank became known as E-Trade Bank.

After the acquisition of Telebanc, Caplan served as chief financial products officer and managing director of E-Trade North America. He also became chairman of the board and CEO of E-Trade Bank. In 2002, Mr. Caplan was named president and COO of E-Trade Financial. In January 2003, after the departure of Christos Cotsakos

Christos Cotsakos

Christos M. Cotsakos is Founder, Chairman of the Board, CEO, and President of EndPlay, Inc.-Early Life & Education:Christos M. Cotsakos is a first-generation Greek-American from Paterson, New Jersey and is fluent in Greek. He is the fourth of five children...

, Caplan became CEO and director of E-Trade Financial.

During his term as CEO, Caplan was instrumental in the strategic acquisitions of Harrisdirect from Bank of Montreal

Bank of Montreal

The Bank of Montreal , , or BMO Financial Group, is the fourth largest bank in Canada by deposits. The Bank of Montreal was founded on June 23, 1817 by John Richardson and eight merchants in a rented house in Montreal, Quebec. On May 19, 1817 the Articles of Association were adopted, making it...

 and BrownCo from JPMorgan Chase.

During the credit crisis of 2007, Caplan was criticized for investing in risky and complex debt instruments. He stepped down as CEO of E-Trade on November 29, 2007. That same day, an agreement with Citadel LLC was announced resulting in a cash infusion of $2.5B.

Since October, 2008, Caplan has advised Aquiline Capital Partners – a private equity firm based in New York and investing in financial services enterprises in industries including property and casualty insurance, banking, securities, asset management, life insurance and financial technology.