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Two summers ago, when Jay Hooley dumped a bucket of ice water over his head in downtown Boston for the viral ALS fund-raiser, the first person he challenged to follow him was his younger brother Stephen.

They are a rare pair of sibling CEOs — Jay at State Street Corp. in Boston, Steve at DST Systems Inc., a smaller provider of data-processing services in Kansas City, Mo.

Their careers have often overlapped, since growing up in Natick, where Steve was backup quarterback to Doug Flutie at Natick High School, and Jay, the eldest of five kids, was into motorcycles.

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Steve went on to pursue engineering at Worcester Polytechnic Institute; Jay studied marketing at Boston College.

Their professional paths would converge at State Street, the giant asset custodian and fund manager where their father worked before them, as a banker. In the early 2000s, the Hooley brothers worked on a major acquisition together, and over the course of two decades each spent years at the helm of joint ventures between State Street and DST Systems.

Today, the brothers oversee companies with a combined market capitalization of $28 billion, and, though 1,500 miles apart, they still do business together.

And oddly enough, one of Steve’s jobs in recent years has been selling millions of dollars’ worth of State Street shares.

Jay is a Wall Street fixture and public presence in Boston business circles, while Steve shuns the spotlight and rarely makes public comments.

Jay is a frequent global traveler who faces routine shareholder scrutiny and flies commercial; his younger brother gets personal use of DST company aircraft.

At the heart of their collaboration is Boston Financial Data Services, a transfer agent that handles transactions and shareholder services for mutual funds that are major State Street clients. It has hundreds of millions of dollars in annual revenue and roughly 2,300 employees, but it barely registers a blip in State Street’s public filings.

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While the joint venture is a 50/50 split, DST is the only one to disclose any of the BFDS financials.

Deep in DST’s annual proxy statement for shareholders, in the “related transactions” section, is more of the story:

Holdings of State Street shares have long been DST’s largest investment. BFDS generated $112.5 million in revenue for DST last year. The venture has made large loans to DST and has paid the Kansas City company dividends, such as a $125 million payment in 2013.

When State Street vice chairman Joseph Antonellis retired last year, he was named to the DST board of directors. He was nominated to the $250,000-a-year, part-time post at Stephen Hooley’s recommendation, according to the filing.

Before him, Edward Allinson, a former State Street executive vice president, sat on the board.

The filing also notes that Hooley’s brother is the chief executive of State Street. For the Boston financial giant, administering trillions of dollars in assets, such a disclosure is “not material,” corporate governance specialists said.

Neither Jay nor Steve Hooley would comment for this story.

Jay Hooley, 59, spent a decade of his career running Boston Financial Data, based in Quincy, and building a similar international operation. He was chief executive of BFDS from 1990 to 2000. It was a job integral enough to State Street’s business that his time at BFDS was credited to his State Street pension, according to a public filing.

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Steve, now 53, was chief executive of Boston Financial from 2004 to 2009, following in Jay’s footsteps. Then he was tapped to go to Kansas City, as president of DST.

In 2011, he got a front-row seat on activist investors pressing the company to sell off some $400 million in State Street stock.

Since the financial crisis, as the Hooley brothers climbed to the top of their respective firms, Jay has been battling a host of issues, from stagnant revenue and regulatory scrutiny to plans for cost cuts.

Steve has been under pressure from investors to sell off noncore assets. Among those: the State Street shares.

DST has sold off the shares in large chunks. At the end of last year, the company still owned 2.2 million State Street shares, valued at nearly $145 million. At the end of the first quarter, their value had declined to $128 million.

“We like that they’re slowly monetizing these assets that really aren’t core to their business, and returning that capital to us,’’ said Jonathan Moody, a portfolio manager at the London Co. of Virginia, an investment manager in Richmond that owns shares of DST.

Building a business of software and high-tech processing for financial and health care clients, the younger Hooley has had the kind of stock performance that a sibling would envy.

DST shares have jumped 33 percent over the past two years, to $119.16. State Street shares have slumped 6 percent in that period, to $59.23.

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About the brothers

Joseph L. “Jay” Hooley

Age: 59

CEO of State Street Corp.

Market capitalization: $24 billion

Employees: 31,000

Stephen C. “Steve” Hooley

Age: 53

CEO of DST Systems Inc.

Market capitalization: $4 billion

Employees: 13,420


Beth Healy can be reached at beth.healy@globe.com. Follow her on Twitter @HealyBeth.