Prior to his election as governor, Guild served in the Massachusetts Volunteer Militia, seeing active duty in Cuba during the Spanish–American War.

[3] He rose through the ranks of the business, making rounds of local woolen manufacturers weekly for news, and developing the Bulletin into an authoritative journal of the trade.

Following the sinking of the USS Maine in 1898, Guild immediately volunteered for service in the Spanish–American War that followed and was commissioned as a lieutenant colonel and inspector general in May.

It was established to counter a similar organization founded by Democrats, and to promote the career of Henry Cabot Lodge.

[6] The club was instrumental in gaining the 1891 party nomination for Charles H. Allen as Governor of Massachusetts; he ended up losing to incumbent William Russell.

In the state convention, he was somewhat unexpectedly upset in this bid by John L. Bates, who won the nomination without significant party leadership support.

Guild stood in favor of reciprocity, but much of the more conservative party leadership did not, and the lieutenant governor nomination went to Eben Sumner Draper, a wealthy businessman and strong protectionist.

The state required medical inspections of school children, and passed a corrupt practices bill banning corporate contributions to political campaigns.

Night work for women and children was banned, a state-run employment service was started, and regulations governing inspection of factories for health and labor violations were strengthened.

Upon seeing a group of men entering the State House, the patient fired, killing Edward Cohen, a trade union leader, mistakenly believing him to be the governor.

In another act highlighting the divisions within the party, Draper vetoed one of Guild's choices for commissioner of the state's board of labor statistics, for his pro-labor stance.

[22] In 1910 President William Howard Taft appointed Guild as a special ambassador to the Mexican independence centennial.

Americans had become increasingly vocal about Russian treatment of its minorities, in particular Jews, who had been subjected pogroms and had fled to the US in significant numbers.

A bill was passed by Congress in 1911 abrogating an 1832 commerce treaty between the countries, which went into effect in January 1913, resulting in higher tariffs and reduced Russian imports.

[23] This took place after Guild's predecessor, William Woodville Rockhill, had recently promoted closer economic ties between the countries, including the possibility of major US investment in the improvement of Russia's backward infrastructure.

The defunct Camp Curtis Guild Composite Squadron of the Massachusetts Wing of the Civil Air Patrol bore his name.