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A Cloud of Dots in O’Garrogate.

What a small and chummy town Hartford is. The scandal involving a state assistance, an insurance agency, City Treasurer Adam Cloud, lobbyist Christopher Cloud, the elusive Earl O’Garro and a missing $670,000 in city funds took a dramatic turn Friday with the news that the tangled mess has become the subject of a federal grand jury investigation.

These probes often make themselves felt in the most unexpected places. How O’Garro’s insurance agency, represented by lobbyist Cloud, snagged $126,320 in a state grant and loan when O’Garro was in arrears in taxes may become one line of inquiry. O’Garro appears to have a connection to Connecticut’s aggrieved first lady, Cathy Malloy. He serves as a member of the board of directors of the Greater Hartford Arts Council. Christopher Cloud is the president of the board. That organization hired Mrs. Malloy as executive director two years ago.

The commissioner of the Department of Economic and Community Development, Catherine Smith, lead the agency that provided the grant and defaulted loan to O’Garro’s insurance agency to move from Windsor to 30 Lewis Street, Hartford. That building is owned by the Clouds. Sanford Cloud, father of Adam and Christopher, is the managing member of the entity that owns 30 Lewis Street. Sanford Cloud and Catherine Smith were colleagues when they both worked at Aetna, Daily Ructions has learned.

The eventful week draws to a close with questions far outstripping answers.