Willie Monroe Jr. hasn’t ever seemed to catch a break. A seemingly lifelong underdog despite having a highly decorated amateur record of 128-14 with 72 of his wins coming by way of knockout. Monroe, the nephew of Willie “The Worm” Monroe, who beat Marvin Hagler, joined the family business in 2008, and now eleven years after his professional debut, Monroe is looking for his crowning moment as his boxing career has been a handbook for overcoming rather than triumph, so far.

Monroe Jr., who rose to fame during ESPN’s Friday Night Fights Boxcino middleweight tournament, as he defeated Vitalii Kopylenko, Brandon Adams and Brian Vera to gain the title.

What did Monroe Jr. win? Well, a Gennady Golovkin fight, probably a bit too soon for when he was ready for it.

Monroe Jr. went from ESPN2 to HBO in no-time flat. Golovkin, who was in his prime in 2015, stopped Monroe Jr. in six rounds. Monroe Jr. rebuilt himself on undercards defeating Boxcino season two tournament winner John Thompson as well as beating world title challenger Gabriel Rosado in the co-main event of the Canelo Alvarez vs. Liam Smith pay-per-view bout.

The impressive outings got him a shot at WBO middleweight world champion Billy Joe Saunders. Once again, Monroe Jr. came up short in his second world title fight, losing a close and competitive decision to Saunders in a bout overshadowed by Saunders son trying to punch Monroe Jr. below the belt at the weigh-in.

Last year, Monroe signed with Al Haymon, the famed boxing advisor who has lead many fighters to millions. Monroe was going to get his third world title shot of his career facing interim WBC middleweight world champion Jermall Charlo, but Monroe Jr. failed a drug test.

Monroe Jr. failed for a testosterone over the counter supplement, and while the details don’t seem accessibly in a public forum, the fact that Monroe is fighting six months after the failure, seems to say that the adverse finding from the December 2018, might not have been the gloom or doom some wanted it to be.

So this Saturday, Monroe faces fellow contender, Hugo Centeno Jr., whose career has taken some detours on the backroads professional boxing circuit. Centeno is known as a puncher, Monroe is known as a boxer – a contrast of styles, that sometimes can lead to interesting match-up.

The winner of this bout seems poised to get a big opportunity, the loser poised to since on the smaller club show circuit on FS1. This is a win or go home for two decorated fighters, who have a lot to lose along with a lot to gain.

Willie Monroe Jr. faces Hugo Centeno Jr. at the Soboba Casino in San Jacinto, California on Saturday, June 1st, broadcast worldwide on FS1.