He lost his title on February 1, 1900, to one of America's greatest boxers, the Brooklyn featherweight Terry McGovern in a fifth-round technical knockout at Tattersall's in Chicago before an impressive crowd of 15,000.

In his early career from 1895 to 1896, he knocked out Young Casey in 3 rounds, Jimmy "Spider" Kelly in 1, Kid Reynolds in 2, the well known Eddie Curry in 4, Jim Gilchrist in 6, and Jack Smith in 1.

In his first sixteen fights between March 22, 1895, and June 1, 1897, he lost only once to the well known fellow Chicago featherweight Tommy White by knockout at the Midway Theater in Lamont, Illinois in August 1896.

On October 10, 1899, Santry overtook the world title defeating Ben Jordan at the Lenox Club in New York in a sixteenth of twenty-round knockout.

[11] Once McGovern defeated Santry, he reunited the Featherweight Title, and gained recognition in both the British empire, and the United States as a World Champion.

Santry had an advantage in height and though he tired in round twelve, he had more energy by the twentieth, when the bout ended with a referee decision in his favor.

The July battle which drew a crowd of 5000 in Kansas City took place shortly after all the delegates had left from the Democratic National Convention which had been held there that week.

[16] Around November 8, 1900, Santry's knee was badly injured while sparring with Californian and Middleweight Champion Tommy Ryan who had several bouts in Chicago that month.

While attempting a side step to avoid a left from Ryan, his ankle turned and the full weight of his body was thrown on his knee joint in a twisting fashion.

[1] On November 29, 1901, he fought future champion Battling Nelson at the Pyramid Athletic Club in Chicago, winning in a six-round points decision.

[20] He fought Tommy Sullivan three times in April and May 1902, with a win by disqualification, and a no contest in Chicago, followed by a loss in a third knockout in St. Louis, Missouri.

Herrera, who was a promising young boxer, had hurt his hands prior to the bout but had fought slightly fewer gifted opponents and taken subsequently less punishment.

[24] He fought Jack Cordell in San Francisco California on November 29, 1904, and lost in a ten-round points decision, which was unpopular with much of the crowd.

[1] He worked during this period and later refereeing fights in several locations, including Gary, Hammond, and Fort Wayne Indiana, as well as Davenport, Iowa.

[31][32][33] He retired from competitive prize fighting around 1911, but stayed active in the sport as a referee, and may have continued to act as a trainer or cornerman for boxers at times.

He served for several years in the State Legislature and helped to sponsor a bill to administer legalized boxing in Illinois which he had submitted by 1915 as a member of the assembly.

[36] Much to his disappointment, the Carroll Bill he supported to administer legal boxing failed to pass the Illinois House of Representatives on May 27, 1915, five votes short of a majority.

[37] As late as July 26, 1918, he was scheduled to act as a cornerman with his friend ex-champion middleweight Tommy Ryan for boxer Eddie McGoorty's bout with Harry Greb in Chicago.

[38] He lost a run for Illinois State Representative in late 1918, causing him a great deal of disappointment, and according to a few sources, a "nervous breakdown".