Ski, Fish, Bike  … and Give Back

By Rebecca Sullivan Delaney ’98

Not many 76 year olds can say they feel as if they’re still in college, but while Bill Maloney ’59 is planning his 55th Reunion from his office in Jackson Hole, Wyo.—2,300 miles from Worcester—he says he feels like he’s a student on the Hill. 

“I feel like I still go there,” he says. “I’ve been involved in so many ways even though I live out here in Jackson Hole.”

This intense connection to the campus and student life at Holy Cross stems from Maloney’s deep commitment through the decades, of time, knowledge and financial resources.

Maloney has taken this commitment one step further by recently announcing his intention to bequeath half of his estate to the College. The bequest will create the Class of 1959 Football Endowment and will also support the Ciocca Office of Entrepreneurial Studies and the Alison Maloney Estep Scholarship Fund. The scholarship honors his late daughter, a member of the Class of 1988, who was killed in an automobile accident in 1993. Maloney’s brother, Gene Maloney ’66, established the scholarship in 2001 to honor his niece. 

After retiring from the financial industry, where he worked as managing director of mergers and acquisitions at Kidder, Peabody & Co., Maloney and his wife, Carol P88, moved to Jackson Hole, Wyo. Retired in name only, he continues to run his own company, Osprey Holdings Ltd., and also serves in leadership roles on three nonprofit boards. He fits in work between skiing, trout fishing and cycling—sometimes all in one day. This past winter he logged 116 days on the slopes. In the spring, when the chairlifts stop running, he straps the skis to his back and climbs to the top of the trail to get in a run. 

This devotion and extraordinary work ethic is evident in his relationship with the Holy Cross community. Almost 30 years ago, Maloney started a Career Night for the football team. He mines his extensive network of football alumni (his daughter Alison was married to Tom Estep ’88, a Holy Cross football player) and asks them to come and talk to students about their profession and career path. The Career Night continues and now dovetails with a more formalized mentoring program for football players and cheerleaders called 90-Wide that Larry Doyle ’83 started in 2009.

Tom Gilmore, head coach of the Holy Cross football team, says players walk out of Maloney’s Career Nights inspired by the alumni players’ achievements in the professional world. And, he says Maloney’s extensive connections are an asset to his players. “Bill is connecting people all over the globe,” he says. “I find many of our kids contact Bill whether they have a mentor or not.” 

Maloney’s commitment to the football program and his alumni connections are, “a huge recruiting tool,” says Nathan Pine, Holy Cross athletics director. “To have this outstanding network of mentors that can help players provides a tremendous recruiting advantage.”  

Of Maloney’s recent bequest intention, Pine says it’s “a statement of his passion for Holy Cross football and his connectedness to the program.” 

Maloney also worked to help develop the Ciocca Office of Entrepreneurial Studies from the ground up and returns to campus each year to serve on a panel of judges for students’ final presentations during the four-week summer business program. During the unique, intensive program, students from any major learn from alumni business leaders about running and launching a business.

“It’s given me a great exposure to the students,” Maloney says of his involvement with the summer business program. 

Maloney is also a member of Holy Cross’ Gridiron Leadership Council, as well as the 1843 Society, and was the recipient of the In Hoc Signo Award in 1997 and the Mathew P. Cavanaugh ’20 Award in 1999.  He has served as class chair for 45 out of the 55 years since his graduation.

Growing up on Long Island, Maloney attended Chaminade High School in Mineola, N.Y. He was a self-described “basketball freak” and became interested in Holy Cross when he saw the basketball team win the N.I.T Championship. He played basketball at Holy Cross for one year. 

Maloney tries to exercise every day and jokes that his active lifestyle might translate to a smaller bequest to Holy Cross down the road. “There might not be much left,” he says, laughing. And while he’s thrilled he is able to make such a significant contribution, Maloney’s wish is that his bequest spurs other alumni to consider the College when planning their own wills.

“My hope is that this will encourage others to do the same thing,” he says. “Holy Cross has been a wonderful part of our lives, and I tell people, when you go to Holy Cross, you join a family for life.”  ■


Writer Rebecca Sullivan Delaney ’98 is from Hingham, Mass.