He was the first Mayor of Boston not of native birth, and his popularity was attested to by his re-election for four consecutive terms. During the first year of his administration, the charter reforms of 1885 went into effect.

Mayor O'Brien was very much concerned about proper methods of street improvements. It had been remarked by an earlier administration, 'that the government of Boston, from its infancy (as shown in its streets) has still within a few years been without method, depending chiefly upon the individual fancy or convenience of property owners instead of being directed by municipal authority.' Mayor O'Brien said that during the previous years Boston had, 'expended millions of dollars for widening and extending streets that could have been saved if some systematic plan had been adopted.'

He was instrumental, under the new charter, in bringing about improvements in street work of great value. Another question of great concern to Mayor O'Brien was that of the tax rate. He believed that it should be limited by law and the maximum placed at $15; but the General Court took the matter into its own hands, and the rate was fixed in 1885 at $12.80, all above the amount of $9 being for the state tax and city debt. He was actually able to keep within the prescribed tax limit of 1885, and to bring the city debt within the 2 per cent limit.

Mayor O'Brien was dissatisfied with the charter amendments of 1885. His predilection was for giving the Mayor full power, saying, 'If he does not do his duty, turn him out.' He asked, 'Why should Boston be singled out for special legislation? In other words, the citizens of Boston ought to be allowed the largest liberty in governing themselves, because they are more competent to organize departments for the efficient government of the city under such general laws.' Throughout his administration, he stood firmly against interference in city affairs by the General Court [state legislature]."

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