Leo Ryan was a quiet, unassuming man, liked by

nearly all who met him, not a mean bone in his body,

yet beneath his appealing nature was a deep love for

boxing, and the sweet science was never a sport for

the faint hearted or those without the willingness to

hit or be hit by another human being.

Ryan was almost scholarly by appearance, with the

demeanor of a college professor and, ironically as it

turned out, he had a direct impact on perhaps the

greatest boxing coach and team in collegiate history.

“Leo was very quiet,’’ said hall of fame trainer Bill Kaehn.

“He wore glasses. You wouldn’t think he would even be

involved in the fight game. He didn’t look the part.’’

Be that as it may, Ryan was renowned for the work

he did in the gymnasiums and corners of some of the

best professional fighters of the time, Del and Glen

Flanagan and Jackie Graves.

“He was like a second father to me,’’ said Kaehn. “He was

an excellent trainer. Everybody liked him.’’

Ryan studied under some of the best fighters of his era,

passed on that knowledge to fighters he worked with

and was a direct link to arguably the greatest collegiate

boxing team of all time.

He worked the corners of the Flanagans, Jackie Graves

and others who were ranked fighters during an era

when such recognition was a mark of high distinction

in the sport and hard to come by with only eight

weight divisions and one or sometimes two recognizing

bodies extant at the time.

Ryan was 3-1 as a professional fighter, those fights

spread over a period from 1906 to 1913. During that

time a story, likely apocryphal, circulated about his

fighting career.

“There was a story going around about Leo, ’’ Kaehn

recalled. “In one of his fights it was said that his twin

brother was positioned below his corner and between

rounds they would switch places. That story went

around for a long time, about Leo and his twin.’’

Fact or fiction, therein lies another clue to Ryan’s nature.

Without evidence that Ryan ever attempted to quash

the story, it can be assumed that he had a bit of the Irish

imp in him, a proclivity for the tall tale, or perhaps the

story was in fact true, an indication in that case that

he enjoyed a bit of tomfoolery.

Kaehn derived his boxing technique from his father,

Earl, who is being inducted alongside Ryan and seven

others into this year’s hall of fame. “Leo’s style was a

little different than ours,’’ Kaehn recalled. “But he was

very good at what he did.’’

Ryan’s techniques have been traced to his studies

under the Gibbons brothers, Tom and Mike, and he

later passed them on to John Walsh, who coached the

College of St. Thomas boxing team and later established

the best collegiate boxing program in the nation at the

University of Wisconsin. Walsh, who also practiced law,

is regarded as the greatest boxing coach in collegiate

history, however brief that era. College boxing’s

championship trophy was, in fact, named for Walsh,

a native of Minneapolis.

In his thoroughly entertaining and insightful book

“Lords of the Ring. The Triumph and Tragedy of College

Boxing’s Greatest Team,” author Doug Moe details much

of the information surrounding Ryan’s influence on

Walsh and the University of Wisconsin team he brought

to prominence, as well as the influences on Ryan. What

we are left with is insight not only into Ryan’s abilities

within his craft but also a glimpse at the talent and

knowledge that was prevalent throughout the Twin

Cities, St. Paul in particular, during a golden era of

boxing in the United States.

Walsh drew large crowds not only to watch the Badgers

box but for the NCAA Boxing Tournament held in

Madison. Assemblages of 10,000, 11,000 or 12,000

were not uncommon. The NCAA team trophy was

named for Walsh, whose topflight coaching technique

had been passed on to him from the Gibbons brothers

through Leo Ryan.

“He (Leo) usually worked with (trainer) Gene Connolly,’’

Kaehn recalled. “They’d work the corner together for

Del and Glen’s fights among others. Leo was sort of a

jack of all trades around the gym. If a fighter came in

without someone to train him, Leo would step in. He

was very good with especially young fighters.’’

The “gym” was typically Potts Gym on Seventh and

Hennepin, where the Flanagans sparred and did their

training.

“There were probably eight to ten of the leading

contenders up there at times,’’ said Jerry Flanagan,

the youngest of the brothers. “It was quite the place.

Leo worked with the O’Sheas too, Brian and Rory’’

Flanagan recalled the boxing gatherings at their home,

and Ryan was frequently among those who were

present. “He used to come to our house after the fights,’’

he said, adding an opinion that was widely shared and

hard to come by in boxing circles, then as well as now.

“Leo had credibility,’’ Flanagan said. “He was honorable

and had a lot of integrity. His word was his bond.’’

Ryan’s boxing career itself was ever so brief, with only

four fights, all of them at various sites in Minneapolis,

yet they spanned a period of seven years. He outpointed

Julius Keller on January 13, 1906 in both fighters’

debuts, and won on points against Jimmy Woods (in his

first fight) the following November. Then, in December,

Ryan won on points against Kid Bartos, who was also

fighting professionally for the first time. Inexplicably,

Ryan didn’t fight again for nearly seven years, losing on

points to Johnny Tillman, who was 13-0-2 at the time.

Ryan worked largely in the shadows of the fight game,

well known to the fighters and their associates but not

generally to the boxing public. Yet, his knowledge and

teaching skills were unmatched in many respects.

He could work a fighter between rounds, restoring

confidence lost to the barrage of punches he had

just taken. And he could take a youngster, new to

the gymnasium, and teach him the basics, or an

experienced fighter and refine his skills. He was

indeed a jack of all trades in a golden era and fully

deserving of a place in the Minnesota Boxing

Hall of Fame.