Though one of the strongest arguments supporting Floyd Mayweather’s frequent inclusion on boxing’s all-time great lists is the staggering roster of elite names he faced, there remain a handful of notable omissions. One absence that continues to puzzle fans is Timothy “Tim” Bradley.

A former two-division champion, Tim Bradley has become a household name for his incisive analysis and sharp commentary. His fighting legacy, however, has long been closely tied to his trilogy with Manny Pacquiao. After losing their rubber match in 2016, he quietly walked away from the sport. Yet it is hard not to wonder how his career might be viewed had it included a bout with Floyd Mayweather. According to Bradley, that opportunity nearly materialized. A potential fight with Mayweather was discussed and even dangled before him, complete with an $8 million payday, only for it to ultimately fall through.

Inside Tim Bradley’s near-miss with Floyd Mayweather

Bradley shared the story on a recent episode of All the Smoke Fight. The revelation surfaced toward the end of the show as he discussed his successful transition into boxing broadcasting. At one point, Andre Ward asked him directly, “Why you never fought Floyd Mayweather?” The question gave Bradley pause.

He then explained that there had been what he described as a “verbal agreement,” or more accurately, a “verbal option,” to fight Mayweather. He did not specify the exact timing. It seems to have occurred in the lead-up to one of his fights with Pacquiao, though he declined to say whether it was the first, second, or third bout.

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“I got that phone call. Tim, you want to fight Floyd? $8 million. Don’t sign to fight Manny Pacquiao. 8 mill, fight Floyd,” Bradley recalled. But the offer immediately raised red flags. Bradley countered by asking for half the money upfront, with the remaining $4 million to be paid when he entered the ring. Over time, he explained, he learned how people easily mislead fighters.

In boxing, false promises are rampant. “Hey, I’m not a fool. So, as soon as they didn’t give me the money or wire me the money, I knew it wasn’t real,” he told Ward.

How close Bradley and Mayweather really came

Privately, however, Bradley admitted he had always hoped for the matchup. Instead, the opportunity ultimately went to Ward’s close friend, Andre Berto. The closest Bradley and Mayweather ever came to sharing the ring occurred under unusual circumstances.

In July of 2015, WBO stripped Mayweather of their title when he failed to pay the sanctioning fee. At the time, Bradley held the interim championship. He was subsequently elevated to full welterweight champion before heading towards the title defense against Brandon Rios.

It remains a fascinating hypothetical. Bradley’s only two career losses came at the hands of Manny Pacquiao. Renowned for his durability and granite chin, he has never been stopped. In all likelihood, a fight with Mayweather would have gone the distance, with the defensive master gradually dismantling Bradley through precision, timing, and technical brilliance. What never happened, however, still lingers as one of boxing’s more intriguing what-ifs.