Cosmo Macero on Steve Bailey

Boston Globe business columnist Steve Bailey’s final column ran on March 28; he’s off to work for Bloomberg News in London. Two days ago, a farewell party was thrown for him at Anthony’s Pier 4. We asked Cosmo Macero—a party attendee, and a former Herald business columnist who competed against Bailey—to pen his thoughts on the departing newspaperman.

Steve Bailey signed off for good from the Boston Globe on March 28 after a remarkable 30-year career bird-dogging the people who make this town tick.

With a measure of influence unlike—and possibly unmatched by—any other Boston newsman, Bailey mastered the art of finding the scoop where lesser journalists weren’t looking. His Downtown column was appointment reading. And he knew that just a sliver of detail found at the intersection of business and government—once properly subjected to his relentless inquiries—could set Boston atwitter and abuzz like no bank merger ever could.

Of course, he generally nailed the merger scoops, too.

“I go through a room, I’m going through people’s pockets looking for stuff,” Bailey told me recently, reflecting a bit on the process he used for some 1,500 columns in the Globe‘s business section. “Everybody knew I was always working.”

Bailey could wax eloquently on derivatives, yet had a laudable tabloid knack for giving nicknames (King Kilts, Governor Slots, Mayor For Life). Sources and subjects became accustomed to having him up in their face, or on the other end of the phone, using that certain South Carolinian drawl filtered through a persistent cough. But he always knew the boundaries.

“Ultimately the sources have the power,” Bailey said. “If you screw them once, you can’t screw them twice. I always like to tell people, ‘I always stabbed you in the chest, never in the back.'”

He had a long and accomplished career at the Globe long before Downtown debuted in 2000. But it is the eight-year run of that column against which all business reporting in Boston has been—and for some time to come will be—measured.

“They read your columns because they can’t help themselves,” former John Hancock chief David D’Alessandro remarked at Monday’s send-off party for Bailey.

D’Alessandro embodies the generation of business and civic stewards that Bailey has routinely relied upon, preyed upon, impressed and incensed. The send-off at Anthony’s Pier 4 saw a parade of such figures—Boston’s Permanent Government—reveling as much in the skewering and savagery they endured from Bailey as in the more infrequent salutes and plaudits he doled out.

But the city is changing. It’s getting younger, faster and less white. Identifying the next generation of Boston business leaders is probably the single most important thing reporters can do to begin filling the void Bailey leaves behind. Getting up in their faces everyday—like Bailey did so well—would be the next step.

And of course, always aim for the chest.

Cosmo Macero Jr. is a vice president at O’Neill and Associates.