Processing Your Payment

Please do not leave this page until complete. This can take a few moments.

Updated: August 22, 2022 / 40 Under Forty, Class of 2022

40 Under Forty 2022: Darryl Caffee Jr.

Photo | Erika Sidor Darryl Caffee Jr.
Photo | Erika Sidor 40 Under Forty, Class of 2022 winners, from left, Ryan Brown, Darryl Caffee Jr., Alise Breton, and David Willens pose at Old Sturbridge Village (special thanks to Christine Freitas and James Donahue)
Darryl Caffee Jr., 36
  • Title Senior vice president, director of retail lending and community reinvestment officer
  • Company Webster Five Cents Savings Bank, in Auburn
  • Residence Shrewsbury
  • Birthplace Landstuhl, Germany
  • Colleges Lock Haven University, Massachusetts School of Law
Click here to read about the other 40 Under Forty, Class of 2022
More Information

Caffee holds many roles at Webster Five, but, in all his work, community investment is a priority and success is a constant.

As the CRA officer, he created a strategic plan for the $1.1-billion bank’s community development efforts, focusing on meeting credit needs for Worcester County’s low- to moderate-income neighborhoods. In addition to this role, Caffee serves as director of retail lending, overseeing the mortgage and consumer lending teams.

Through his tenure, the department has seen continuous growth, reaching record highs in the past two years. In Caffee’s four years with Webster Five, he has helped generate a 600% increase in fee income compared with the previous four years. He uses his expertise in lending to assist homeowners and hopeful homebuyers around the community by serving on the board of directors for the Massachusetts Bankers Association and focusing on affordable housing initiatives. He serves on the Mortgage Review Board for the Massachusetts Division of Banks to ensure Worcester County residents are not discriminated against during the loan application process. 

What four people would you take a 10-year, deep-space mission? My wife, my dog, Bobby Flay, and Elon Musk.

What will Central Mass. be like in 10 years? I see Central Mass. as a hub for life sciences and business (small and large) with a great housing market driven by continued population growth.

Who is most responsible for the person you are today? My parents aside, I grew up in suburban Philadelphia. During my childhood, I idolized Kobe Bryant and Allen Iverson. They set my baseline for work ethic and determination.

Sign up for Enews

WBJ Web Partners


Order a PDF