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In addition to the donations by RapidTrans and Chartered Family Health Center, Mr. Thompson and his accounting firm each donated $4,000 on the same day. Several associates and employees of Mr. Thompson’s businesses also made donations.

Lee Calhoun, a principal at Thompson, Cobb, Bazilio & Associates, donated $1,000. He and Michelle Calhoun, who resides at the same Silver Spring address, were among those who each donated $4,000 to Mr. O’Malley’s campaign on Sept. 22, 2010, and contributed maximum donations to a number of campaigns in the District on the same days as other associates of Mr. Thompson.

Others who donated on the same day to Mr. Brown’s campaign are David W. Wilmot, a D.C. lobbyist who has represented Mr. Thompson’s companies; Francis Smith, a senior vice president at D.C. Chartered Health Plan; Mr. Lawson; and Michelle Haywood, a spokeswoman for Insuraty.

According to Maryland taxation records, Insuraty had its business license forfeited in October 2009, yet campaign contributions were made on the company’s behalf in 2010 and 2011. The company was among those that donated to Mr. O’Malley on Sept. 22, 2010, giving $2,500.

Mr. Smith in an email response to questions declined to comment about his two $500 donations. Neither Mr. Lawson, Ms. Haywood, nor any of the other contributors named returned messages seeking comment.

Peter V.R. Franchot

Four of the same people who donated to Mr. Brown and Mr. O’Malley on the same days also gave money to Mr. Franchot on a single day in 2008 — the same day of a $3,000 contribution from D.C. Healthcare Systems.

Mr. Thompson, and Lee and Michelle Calhoun all gave $3,000 to Mr. Franchot’s campaign on October 22, 2008. Mr. Lawson donated $200 on that day.

Three others, also with ties to Thompson, Cobb, Bazilio & Associates, gave an additional $8,000 to Mr. Franchot on that day.

Lawrence Wilson, a principal at the accounting firm, and Gloria Wilson, who resides at the same Bowie address as Mr. Wilson, both gave $3,000. Joseph Wilson, who lists Mr. Thompson’s accounting firm as his employer in national campaign-finance records, gave $2,000 on that day. The same three individuals are responsible for at least $55,950 in political donations to candidates running for office in the District since 2002, according to D.C. campaign finance records.

Mr. Franchot, a Democrat also considered to be preparing for a 2014 gubernatorial run, appears to have collected at least $20,200 on that day alone from Mr. Thompson’s associates and affiliates. The donations came after his 2006 election to the statewide office of comptroller and as he was ramping up for re-election efforts in 2010.

Mr. Franchot’s office referred questions to campaign officials, who did not return requests for comment.

County executives

While donations to some politicians are clustered on specific days, a broader look at the donations that those in the Thompson network gave shows a wide range of Maryland recipients who benefited.

Among others, Mr. Thompson gave $4,000 contributions — the maximum amount allowed per candidate per election cycle — are Mr. Ehrlich, former Lt. Gov. Kathleen Kennedy Townsend, former Montgomery County Executive Douglas M. Duncan, former Baltimore City Council member Kenneth Harris Sr., and former state Delegate Herman Taylor.

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