Taking the NYSAC World Lightweight Title from Beau Jack, May 1943

Montgomery won recognition by New York state as Lightweight Champion of the World after beating Beau Jack by a fifteen-round unanimous decision on May 21, 1943. Jack won the first round by a wide margin with a flurry of uppercuts and his signature free-wheeling, constant punching from many angles. But Montgomery quickly settled down and scored frequently with a strong straight right that at times had Jack close to a knockout and against which he could find no adequate defense. Jack's eyes were virtually closed during much of the bout, but Montgomery's injuries were restricted to a cut above one eye. A right to the chin briefly knocked Jack to his knees in the eleventh round and he struggled in the remaining rounds. One ringside reporter gave Montgomery eleven rounds to only four for Jack.^[7]

Montgomery beat Petey Scalzo in a sixth-round TKO in Philadelphia on October 25, 1943, in Convention Hall in Philadelphia. Montgomery knocked down Scalzo three times during the bout.^[1]

Re-taking the NYSAC World Lightweight Title from Beau Jack, November 1944

He retook the title from Beau Jack on March 3, 1944, at Madison Square Garden in a fifteen-round split decision before 19,066 fans.^[1] Jack had led in the early betting. The fighting was fierce and close throughout and Montgomery was given no more than a two-round advantage by the judges or referee, though the Associated Press scored the bout 8 for Montgomery, 4 for Jack, and three even.^[11] After the bout, Montgomery was drafted into the US Army.^[4] He continued to box while serving in the Army and was released by June 1946, when he defeated Allie Stoltz.^[12]

On February 13, 1945, Montgomery had a fierce bout with Cecil Hudson at the Olympic Auditorium in Los Angeles, California, winning in a ten-round decision. Montgomery received a furlough from active Army duty at Luke Field Arizona, and had not appeared in a competitive match for four months.^[1] Through the first six rounds, Montgomery was perplexed by Hudson's dodges and weaves, and unable to land many solid blows. Hudson was knocked to the canvas after the bell in the fourth, and was down very briefly in the eighth and ninth rounds, once Montgomery found his range. Until the two knockdowns, Hudson was leading slightly in points, according to the United Press scoring. In the fury of fighting, one source noted that Montgomery was penalized in a few rounds for hitting after the bell.^[13][14]

Defending the NYSAC World Lightweight Title against Allie Stoltz, and Wesley Mouzon, 1946

He successfully defended his second NYSAC World Lightweight Title against Allie Stoltz before 10,872 fans at Madison Square Garden in a thirteenth-round knockout on June 28, 1946. The telling blow was a right to Stolz, 2:54 into the thirteenth, but in a decisive win, Montgomery put Stoltz on the canvas as many as five times prior to the final knockout. Stoltz was down in second, sixth, and eleventh rounds. He may have lacked conditioning from his four and a half month layoff from the ring. He fought gamely and continued to take punishment, even landing a solid right to the chin of Montgomery in the sixth round.^[15][16][17]

On November 26, 1946, Montgomery defended his NYSAC World Lightweight Title against Wesley Mouzon in an eighth-round knockout at Convention Hall in Philadelphia, Pennsylvania before a substantial crowd, of 12,416. Surprisingly, he had just lost to Mouzon by knockout in a non-title bout only three months previously on August 19, 1946, at Shibe Park in Philadelphia. In their fiercely fought November title match, Mouzon took the first three rounds with speed and jabs, but Montgomery countered with body blows and rights, before ending the bout 2:18 into the eighth with a long left hook.^[18] Mouzon took a serious lacing throughout all but the first round, and had a serious injury to his right eye.^[19]

On February 7, 1947, Montgomery had a difficult loss to Tony Pellone before a crowd of 11,365 at Olympia Stadium in Detroit in a ten-round unanimous decision. The Associated Press wrote that the crowd was satisfied with the decision for Pellone even though he was the underdog in the bout. Pellone took the aggressive with hard punches to the face and head of his opponent. Montgomery slipped to the canvas in the second for a count of two.^[1][20]