Unfortunately for him, some fights slipped through his fingers.

Manny Pacquiao, without question, is one fighter The Ring's 2025 Fighter of the Year Crawford, desperately wanted to share the ring with, but the legendary eight-division world champion opted to pursue other fights.

Outside of Pacquiao, there are other fighters Crawford wishes he mixed it up with. One of them he shared the ring with as a teenager.

“Danny Garcia,” Crawford said to a group of reporters and fans. “That’s my boy. I think me and Danny would’ve made for a great fight being that we knew each other real well. We grew up in the Junior Olympics and Silver Gloves together. If anyone there was anyone that I came up in the amateurs with that would’ve made for a great fight, it would’ve been him.”

Garcia (38-4, 22 KOs) and Crawford (42-0, 31 KOs) fought as amateurs. Garcia took home a one-point victory over Crawford in the 2006 USA Championship semi-final. A few months later, in the Blue & Gold National Championship final, Crawford eked out a close decision.

That amateur rivalry never crossed over to the pro level, despite their success. Garcia was widely considered the best 140-pounder in the world thanks to wins over Amir Khan, Lucas Matthysse and Zab Judah. But while he was busy defending his Ring, WBA, and WBC junior welterweight titles, Crawford was making a name for himself one division lower.

By the time Crawford moved up in weight, Garcia was long gone. They did compete in the same division, but that was only for a short amount of time. Garcia became WBC welterweight champion in January 2016, but eventually lost his strap to Keith Thurman in March 2017. Crawford, after fully unifying the junior welterweight division, didn’t grab a welterweight trinket until 2018 thanks to his 10th-round stoppage win over Jeff Horn.

From there, they continued to go in opposite directions. Garcia remained in the welterweight division until late 2020. After an inactive period, he returned at 154 pounds. He also made a brief trip to the middleweight division, losing to Erislandy Lara as he attempted to become a three-division champion. The Philly star officially called it a career following his fourth-round stoppage win against Daniel Gonzalez last October.

Crawford’s success went on for years after Garcia’s final championship run. He eventually became undisputed champion at 147 pounds by beating Errol Spence Jr. in 2023. He then ended his career after beating Canelo Alvarez last September to become boxing’s first three-division undisputed champion in the four-belt era.