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Area insurance firm, with acquisition, expands to Florida’s east coast

Clearwater-based Clegg Insurance Group adds more than 1,500 clients with iCan Benefit Group deal.

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  • | 12:22 p.m. October 15, 2020
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Courtesy. Clegg Insurance Group CEO Ryan Clegg.
Courtesy. Clegg Insurance Group CEO Ryan Clegg.
  • Tampa Bay-Lakeland
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CLEARWATER — Clegg Insurance Group has acquired the property and casualty insurance division of Boca Raton-based iCan Benefit Group. 

According to a press release, the deal adds more than 1,500 clients to the Clearwater-based firm’s book of business. It’s the fourth acquisition for Clegg Insurance Group since the company was founded a decade ago. 

Clegg, the release states, will maintain a local office in the Boca Raton and West Palm Beach area. Other terms of the deal were not disclosed. 

“Personally, I’m excited to take on a bigger role in the south Florida insurance space, as I began my career just down the road in Boca Raton with a national brokerage house before starting my own business,” Clegg Insurance Group CEO Ryan Clegg states in the release. “We’re not only excited about adding the new physical office location, but we’re elated to add this very talented existing team to our roster, which will continue to service our customers throughout the area.”

The iCan Benefit Group deal, the release states, increases Clegg Insurance Group’s annual premiums to approximately $15 million per year, moving the agency into a larger insurance brokerage category. The firm’s portfolio of acquisitions also includes Safety Harbor-based Florida Insurance Partners, in 2013; Tampa-based Hopf & Hopf, in 2014; and Anna Maria Island-based Advanced Insurance Brokerage, in 2018.


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