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Even Brown’s staff had Mr. Bailey’s interests at heart. An exchange between Brown’s former chief of staff, Amy Bellanca, and Intralot’s general counsel, Jay M. Lapine, suggests Ms. Bellanca reviewed the Intralot contract with Mr. Bailey as it was being finalized.

“This is it!” Ms. Bellanca wrote to Mr. Lapine in a March 3, 2010, email copied to Mr. Bailey. “Amy: Many thanks for the review,” came the reply from Mr. Lapine, also copied to Mr. Bailey.

Ms. Bellanca did not respond to requests for comment.

“[Houston] we have a problem!” Mr. Bailey wrote to Brown’s private email that same month, as negotiations hit a bump in the road.

Byron Boothe, Intralot’s vice president for government relations, said his company has been cooperating with investigators in the lottery probe, and that neither he nor Mr. Lapine could comment on the case. But he said Mr. Bailey is doing a good job with the lottery.