Sherdog’s Weekend Boxing Preview

What: Masayuki Ito vs. Jamel Herring, Junior Lightweights

When: May 25
How to Watch: ESPN 10 p.m. ET
Why You Should Care: To see if the motivation of being a two-tours-in-Iraq Marine veteran fighting on Memorial Day weekend, and a grieving father fighting on what should be his daughter’s 10th birthday, is enough for Herring to overcome his underdog status.

In sports, we love the story of an underdog who is too motivated to lose. In boxing, the most famous example of this is of course Buster Douglas’ win over Mike Tyson. While pundits will talk about Tyson’s lack of motivation, increased headhunting, decreased head movement, and the odd nature of fighting in a quiet Tokyo arena, the mainstream sports media had only one story they wanted to tell. Douglas’ mother died just days before he was to fight Tyson. He promised her he would become a champion. He was too motivated to lose.

What does this have to do with Jamel Herring? Well, Herring is an underdog in his fight with WBO junior lightweight champion Masayuki Ito. Ito has beaten guys like Christopher “Pitufo” Diaz and Evgeny Chuprakov and hasn’t lost since 2015, while Herring has fallen short the two times he tried to step up in competition: a 2017 decision loss to Ladarius Miller and a 2016 stoppage loss to Denis Shafikov. He’s certainly not a Douglas-level underdog, but make no mistake, he is expected to lose.

Except, Herring has one of those great motivational stories going into the fight. Herring was a Marine who served two tours in Iraq and openly talks about how any soldiers he knew that died overseas. He will be fighting on Memorial Day weekend, which also would have been the date of his daughter’s 10th birthday had she not died of SIDS. While he obviously loves those who died in the line of duty, he is dedicating this fight to her.

With the winner likely to face Miguel Berchelt, we have a good matchup that Ito should win, but Herring has that special kind of motivation that can propel people to greatness they were never supposed to attain. We’ll see if he can be one of them.

What: Jose Pedraza vs. Antonio Lozada, Lightweights

When: May 25
How to Watch: ESPN 10 p.m. ET
Why You Should Care: To see if Jose Pedraza can bounce back from his loss to Vasiliy Lomachenko, or Antonio Lozada can end another hyped Puerto Rican’s title dream.

Last March, Antonio Lozada stepped into the ring with Felix Verdejo, the Puerto Rican fighter that was considered the next big thing from the island nation that produced Felix Trinidad, Miguel Cotto and Wilfred Benitez. It was expected to be an easy win for Verdejo, so much so that the fight took place in Madison Square Garden and was timed to coincide with the Puerto Rican day parade. Instead, Verdejo tired in a fight he was thinly winning, before getting dropped in the 10th and final round. When he got up, the doctor looked at him and stopped the fight.

Lozada is no bum; he’s 40-2 with 32 knockouts. But the stoppage was questionable, and a pressure fighter like Lozado was a horrible matchup for Verdejo to take coming off an over one-year layoff. Most people came away with the idea that Verdejo was overhyped, not that Lozada was anything special. And while Verdejo’s people are still trying to promote him -- and laughably trying to set up a fight with Lomachenko, whom he fought and lost badly to in the Olympics -- it looks like the loss to Lozada essentially killed his world title dreams.

Lozada has the chance to do the same thing to another Puerto Rican star, but he won’t be denied credit for a win this time. Pedraza has already held the WBO lightweight title, and has only lost to Lomachenko and Gervonta Davis. If Lozada can end his title dreams, he will get full credit for beating a good opponent, and a very big-name opponent sooner rather than later.

Jose Pedraza is either going to bounce back from his loss to Lomachenko and put himself in the title hunt at either 135 or 140, or Lozada is going to end the dreams of another one of Puerto Rico’s boxing superstars. On Saturday, we’ll see which.

What: Austin Trout vs. Terrell Gausha, Junior Middleweights

When: May 25
How to Watch: Fox Sports 1 8 p.m. ET
Why You Should Care: To see if a Floyd Mayweather Sr. infused “fresh start” can get Austin Trout to turn marquee losses into marquee wins.

Austin Trout has five losses on his resume, but they are all to elite, household name fighters. Yes, after beating Miguel Cotto in 2012, Trout has lost to Canelo Alvarez (in a fight many in the boxing media believed he won), Erislandy Lara, Jermell Charlo, Jermall Charlo and Jarrett Hurd. That means in terms of easily recognizable competition, he has one marquee win, and five marquee losses. Worse, since the 2012 victory over Cotto, Trout is 5-5 as a professional. No matter who you’re facing, that’s not good.

Hoping for a “fresh start,” Trout has begun working with Floyd Mayweather Sr. What he can add to Trout’s repertoire fourteen years into his professional career will be interesting to see, though it should be noted he did well with an older Oscar de la Hoya.

Terrell Gausha is a 31-year-old former Olympian, who also lost to Erislandy Lara, the only loss of his career. His level of competition has not been as high as Trout’s, but his amateur record was far better, including having won the USA National Championship in 2012 by defeating Caleb Plant.

Austin Trout is in a strange position; he constantly gives the best fighters in the world great fights but can’t seem to beat them. Now, he will look to Floyd Mayweather Sr. for a “fresh start” in hopes of learning how to beat great fighters, not just challenge them.

What: Chordale Booker vs. Wale Omotoso, Junior Middleweights

When: May 25
How to Watch: Fox Sports 1 8 p.m. ET
Why You Should Care: To see which fighter that turned his life around at a young age, can take advantage of their second chance.

Wale Omotoso has three losses as a professional, but they were all to undefeated fighters. Originally from Nigeria but now fighting out of Oxnard, California, Omotoso is 27-3 with 21 knockouts. He hasn’t fought since 2017, but knocked down Jessie Vargas, in a fight he would ultimately lose, and has faced guys like Jamal “Shango” James.

But what’s more fascinating about Omotoso is his life story. Wale Omotoso calls himself “Lucky Boy” because he’s lucky to be alive. He began boxing when, after being orphaned, he joined a street gang and saw people get killed on a near-daily basis. After a vicious machete fight, his gang splintered and ran in fear of retribution from the other gang, so he packed up and fled to another city. That city had a boxing gym. But what if it didn’t?

Chordale Booker calls himself “The Gift,” but he was an incredibly lucky boy himself. As a 15-year old, a judge sentenced him to three years’ parole instead of the mandatory 13 years in prison for various drug offenses. He turned his life around, and is now a 14-0 professional boxer, runway model, and head of the “Go the Distance Foundation” which seeks to break down the barriers between the police and at-risk youth. His life was saved by a judge showing mercy on him, but what if he didn’t?

Booker is another undefeated foe for Omotoso, but he doesn’t have the experience that Wale Omotoso has as a professional. It’s often said that sometimes, it’s better to be lucky than good. Well, both these guys have already been lucky. When we put them in the ring together on Saturday, we’ll see which one is too good.

What: Devin Haney vs. Antonio Moran, Lightweights

When: May 25
How to Watch: Dazn 7 p.m. ET
Why You Should Care: Because we’ll either find out why Devin Haney is so cocky, or Antonio Moran will beat the confidence out of him.

Devin “The Dream” Haney is not a young man void of confidence. The undefeated (21-0 with 13 knockouts), 20-year old former boyfriend of Blac Chyna who already runs his own promotion company, gave an interview this week in which he said at various points, “When I’m the face of boxing”, as well as “To be a World ruler at 20 would be history, the youngest in the game. My ring IQ at my age is crazy, I'm able to adapt and adjust, I've been in there with so many great fighters like Floyd Mayweather Jr., Shawn Porter, Amir Khan, and I'm able to adjust.”

That’s a lot of bluster for a fighter that hasn’t even challenged for a world title, and is only in the main event spot of this card because Oleksandr Usyk got injured training for his heavyweight debut.

Antonio Moran is 24-3 with 17 knockouts and fought Jose Pedraza last June. He believes (and is probably correct) that he’s the best fighter Haney’s ever fought, and that his experience will carry him to a victory (it probably won’t). Still, he’s lost three times as a professional, including losses to fighters with 13-7 and 29-10 records. That doesn’t bode well for him, or the idea that he can deal with Haney’s boxing abilities.

Will Haney show is why he is so confident, or Will Moran show him that being “in there” with great fighters, isn’t the same as actually having faced world champions in the ring?