Billy Bulger said, "If you could keep my brother out of trouble, that would be a great help," according to Martorano.
Martorano testified that he, Whitey Bulger and the others agreed that Whitey would meet with Connolly and "be a good listener." It wasn't long before Whitey Bulger was giving Connolly money and buying gifts including unset diamonds for Connolly to give to his fiancee as an engagement present, Martorano said.
Prosecutors and law enforcement officials say it was the corrupt relationship between Whitey Bulger and Connolly that allowed Bulger's criminal enterprise to grow and even facilitated some murders.
The trial, which enters its fifth day Tuesday, is expected to take up to three months and has the potential to reveal sensational details about the mob and FBI corruption, especially if Bulger chooses to testify.
Bulger was in hiding for 16 years before he was captured in Santa Monica, California, two years ago, living under a false name with his girlfriend in an apartment.
At his July 2011 arraignment, he pleaded not guilty to the 19 murder charges and 13 other counts.