Bermuda-based Endurance Specialty Holdings Ltd. announced on Tuesday that its board of directors elected John R. Charman as Endurance’s chief executive officer, replacing David Cash, who is stepping down from the CEO spot.

Charman will also become chairman of the board of the directors, with William H. Bolinder, Endurance’s current chairman, becoming the lead director.

Cash will also relinquish his role as a member of the board.

The moves are effective immediately, Endurance said in a statement.

Charman was the founder of AXIS Capital, another Bermuda-based insurer and reinsurer, where he served for more than a decade as the CEO and president.

Cash has been a director at Endurance since May 2010, and CEO since March of the same year. Prior to that, Cash had served in the roles of chief underwriting officer (from December 2005 until March 2010), president of Endurance Bermuda (from December 2004 to December 2005) and as the company’s chief actuary and chief risk officer from December 2001 to June 2005.

Both Endurance and AXIS Capital are members of the Bermuda “Class of 2001,” formed in the wake of the 9/11 attacks.

Charman, 60, has four decades of global experience in the insurance industry—first as an underwriter and then as a chief executive. He held his first CEO role at Tarquin plc, the parent company of the Charman Underwriting Agencies at Lloyd’s, which was sold to ACE Limited in 1998.

In today’s statement, Endurance’s director, Bolinder, highlights Charman’s “outstanding leadership qualities, global insurance experience and the demonstrated ability to attain strong and consistent operating performance.” Prior statements from AXIS have similarly cited Charman’s track record for improving underwriting ratios, managing risk and building AXIS from the ground up to a company with more than $5 billion in shareholders’ equity by the time his resignation as AXIS CEO was announced in late 2011.

Still, Charman’s career as an executive has taken several unexpected turns since his Lloyd’s tenure.

In March 2001, for example, ACE announced that Charman would leave the company, “as a result of differences…over personnel matters,” soon after being named group president and chief executive officer of the ACE International Group.

Then in 2006, AXIS announced that Charman would retire as CEO, explaining that he would leave when his employment contract expired in 2008, and that the decision was precipitated by an expensive divorce proceeding he was involved with in the United Kingdom.

By the time 2008 rolled around, however, AXIS announced that it had extended Charman’s employment contract for another five years—until 2013—with then-Chairman Michael Butt praising Charman’s record with the company. “AXIS Capital continues to perform exceptionally well under John’s focused guidance and, indeed, the results speak for themselves. Since John founded the Company in 2001, AXIS Capital has completed six consecutive years of continuous progress in becoming one of the leading specialty insurance and reinsurance companies in the world and our shareholders have received excellent returns on their investment in AXIS Capital.”

In December 2011, AXIS again said Charman would retire as CEO, this time in May 2012, but that Charman would remain with AXIS in the position of chairman of the board of Directors, succeeding Butt, who would be stepping down as chair. (AXIS’ CFO Albert Benchimol replaced Charman as CEO.)

In June 2012, the picture changed again, with Butt now replacing Charman as chairman of the board.

At the time, AXIS explained that the change in board leadership came after the board endeavored to resolve differences with Charman “over his understanding of the role and responsibilities of the chairman position. After the Board and Mr. Charman were unable to reach a resolution, the Board concluded that the company would be best served by someone else serving as chairman and terminated Mr. Charman without cause from the position of chairman under the terms of his employment agreement.”

Meanwhile, Cash’s tenure as Endurance has been less fitful, but not entirely uneventful.

Days after taking the reins as CEO from Kenneth LeStrange in the first-quarter of 2010, Endurance’s largest shareholder demanded that the company consider capitalizing on a consolidation trend he believed would take hold in Bermuda market, expressing concern that Cash was not the man to lead that charge. (Endurance has since bought out the shareholder, Richard Perry of New York-based Perry Corp., according to a January 25, 2011 report in Bermuda’s Royal Gazette.)

Cash had a long career in the industry prior to joining Endurance. A Rhodes Scholar and a native of Bermuda, he joined Endurance from Centre Solutions Ltd. in 2001, where he had been a vice president focused on structured finance and insurance programs since 1996. Between 1993 and 1996, Cash was vice president and underwriter at Zurich Re Centre, and prior to that he served as a consulting actuary at Tillinghast-Towers Perrin in New York.

Today’s statement from Endurance notes that Charman, prior to his joining Endurance, has become one of its largest shareholders (together with his family) with the purchase of $30 million of the company’s ordinary shares.

Charman said: “In support of my strong belief and commitment to Endurance’s future and to fully align myself with the company’s shareholders, I am investing a significant amount of my own capital in Endurance as well as foregoing any conventional compensation over the next five years in exchange for a single grant of restricted shares and options.”

The Endurance statement explains that as an inducement to his employment with Endurance, Charman will receive a stock option to purchase 800,000 ordinary shares at an exercise price equal to the opening price of Endurance’s ordinary shares on May 28, 2013, and a grant of 708,890 restricted shares. The awards will vest over the next four years, subject to Charman’s continued employment, or in the event of certain terminations of employment and other events.

Charman will receive a minimal base salary and no incentive compensation over the next five years, the statement says.

Charman’s appointment is subject to the approval of the Bermuda Department of Immigration.

Commenting on the change in command, A.M. Best said that financial strength, credit and debt rating are unaffected, adding that “A.M. Best expects that Mr. Charman will be an agent of change at Endurance,” and that the rating agency will continue to monitor future developments.