Throughout his twelve years as mayor, Michael Bloomberg, the grandson of Russian immigrants, had a number of “interesting” moments with the Irish community. At the close of his time in office, let’s take a look back at some of his most notable encounters of late:

The one that received the most widespread media attention wasn’t exactly positive. IrishCentral broke the story in February 2011 about the bizarre and insulting remarks Bloomberg made during the launch of a book about the St. Patrick’s Day Parade at the American Irish Historical Society.

Explaining that he lived nearby, the mayor said he was used to seeing "people that are totally inebriated hanging out windows" at the society, which occupies a handsome townhouse on Fifth Avenue.

Bloomberg’s attempts to be culturally sensitive/relevant have often been fodder (see the popular “Miguel Bloombito” Twitter account), but a number of outlets ran with the story, from a thoughtful piece in the New York Times, to the Daily News’ declaration of Bloomberg as “Knucklehead of the Week.”

He eventually issued a public apology, explaining that he was referring to the party held by the Society on St Patrick’s Day every year. “It’s traditional to hang out the window and yell and scream, and it’s all in good fun,” he said. “I apologize. I certainly did not mean to offend anybody.”

Nothing could have been further from the truth for those who know the genteel nature of that particular event of course.

It was a doubly hard St. Patrick’s day for Bloomberg, as 2011 - the parade’s 250th anniversary -  was the first year the city insisted that it follow a shortened route.

Bloomberg was once again in the dog house for St. Patrick’s day 2012, when the Irish community of Rockaway booed and heckled his appearance in their annual parade. The parade was a special moment in Rockaway, bringing camaraderie and good cheer to the community, which had been so devastated by Hurricane Sandy months earlier.

As one local resident declared, “I booed loudly. We had no food, no shelter. People died here, and Bloomberg was on TV talking about a marathon. It’s appalling.” She was referring to Bloomberg’s insistence after the storm that the New York City Marathon go ahead (it didn’t), making it a top priority despite dreadful conditions in the Rockaways and elsewhere.

But despite the sometimes tempestuous relations, New York’s Irish showed their support for Bloomberg in the 2009 election.

Analysis by the New York Times showed that  Irish and Italians in the boroughs of Queens, Brooklyn and Staten Island provided the margin of victory for Bloomberg in a much tighter contest than was anticipated.

In an exclusive interview before the 2009 election, he told IrishCentral’s founder Niall O’Dowd of his great esteem for the Irish - in particular for their work ethic.

He has also been a loud and forceful voice for immigrant rights and immigration reform.

Along the rocky road towards economic recovery, Bloomberg has offered support, guidance and practical help to the economies and governments of Northern Ireland and the Republic - introducing valuable connections, and bringing jobs and connectivity via his Bloomberg News business. In 2012, they hosted the first Bloomberg Ireland Economic Summit, bringing both Irish and internationally recognized economic authorities together in Dublin to discuss Ireland’s way forward.

In September, when Bloomberg announced his decision not to endorse any of the candidates vying to replace him as New York City’s mayor, he gave one of the New York Irish-American community’s figureheads a big shock. It had been widely assumed (despite a long delay and reports that he had been courting Hillary Clinton for the post) that Bloomberg would endorse Speaker Christine Quinn, his long-time ally in city politics.

Perhaps, given the heat Quinn took for supporting his move to extend the mayoral term limits, Bloomberg's endorsement would in fact have been her campaign's final death kiss, but his choice not to endorse her was undoubtedly a big blow to Quinn.

He did however stick with his Police Commissioner Ray Kelly, his most important appointment, and together they brought crime down to historically low levels.

It’s been an interesting 12 years, and the future of New York has been forever changed. NPR’s Margot Adler summed up what, for better or for worse, we’ll miss about Bloomberg as mayor:

“Mayor-elect de Blasio talks of a tale of two cities, and there's truth in that. But as a reporter covering a man who spoke his mind no matter what, it was often a pleasure.”