Bellator 253 Featherweight Grand Prix Betting Odds and Picks

The boys over at the big B are really doing their darndest to catch up with the UFC. This event will pull them within one event of the UFC’s 254. The Ultimate Fighting Championship has, of course, put on way more events in total.

They only count their pay per view shows. Before UFC 255 this weekend, Bellator 253 goes down and I believe we have some betting solid spots for you guys.

Everything didn’t go as planned last week. I thought Pedro Carvalho had somewhat of a chance against Patricio Pitbull Freire but I was wrong. We did have an underdog play on Logan Storley to upset fellow unbeaten Yaroslav Amosav and we got a split decision.

As a near 2 to 1 underdog, a split decision doesn’t break my heart but it doesn’t fill my wallet either so I wanted to dig a little deeper this week.

The main event features one of MMA’s most talented 25 year olds, the second generation pro fighter, AJ McKee. His father Antonio was a pretty good fighter as well and even competed in the same Bellator event as his son last year.

He will be facing the toughest test of his 16-0 career, though, when he fights wrestling ace, Darrion Caldwell. Darrion is a former Bellator world champion. He isn’t your typical wrestler, though, with a short and stocky frame. He is very lengthy and prefers the leverage approach to strength.

I don’t think this will be a walk in the park for AJ at all but I do feel he is the more well-rounded fighter. If he blows through Caldwell then, wow, we know the man is now a problem.

Former WEC and UFC World Champion Benson Henderson is in the main event and an underdog to the ever-improving Jason Jackson. At first glance, I thought this might be a good dog play but Jackson is peaking and has the athleticism to match and possibly better Smooth Henderson.

When you get two great athletes in there, though, a lot can happen. We just saw Khaos Williams upset Razak Al Hassan and sizeable underdog Joaquin Buckley’s jump spinning back kick to the face of Impa Kasanganay was pretty gnarly as well.

There are a lot of mismatches on this card so we may go the way of the parlay.

Betting odds brought to you by the good folks over at BetOnline.AG.


One fighter I like to get it done at Bellator 253 is Jeremy Kennedy. The 15-2 Canadian fighting out of my home away from home, Chiang Mai, Thailand at Team Quest is going to be a problem for journeyman Matt Bessette.

Matt is out of Hartford so you know he is angry. I have had nothing but bad experiences in Hartford and almost all good in Chiang Mai.

Kennedy has a recent win of Steven Siler who is on another level than Bessette.

This one should be clean.

Joey Davis is going to be the second leg of our parlay. He is a dominant wrestler out of Notre Dame, the Ohio version that is. The 7-0 Compton, California native has a great frame at 5’11” tall with nearly a 76 inch reach.

Like our main event fighter AJ Mckee, Joey Davis has had all of his professional fights inside of the Bellator cage. The company has done a good job with these prospects and that is even more reason to bet them because they are being set up to win.

Davis has finished his opponents in a variety of ways including hammer fists, flying knee, overhand right, and even a spinning back kick to the body. This is coming from a 26 year old wrestler who has only been pro for a little over 4 years.

His opponent, Bobby Lee, was 6-4 under the LFA banner and a good fighter who will work for your money but in the end, I think that would be money wasted.

Throw AJ McKee on there for nearly even money at (-115).

This means you are essentially getting AJ, a (-335) fighter, at (-115). Go for it.

Pick: McKee + Davis + Kennedy

Jason Jackson (-175) vs Benson Henderson (+145)

I will spare you the unedited nickname of Jason Jackson but it rhymes with grass kicking machine. Creative these guys are, I tell ya.

Jackson is a great athlete whose speed and length are probably unmatched in the Bellator Welterweight Division. Standing at 6’1″ tall, his reach spans 78 inches. The Kingston, Jamaica-born Jackson now resides and fights out South Florida at Sanford MMA with the likes of Kamaru Usman and Gilbert Burns.

I first remember Jackson from seeing some sparring wars he would have with Michael Johnson back when they were called the Blackzilians. I thought, who is this guy? He is really getting after this UFC guy but it was back and forth much like the career of MJ.

Don’t ever bet on Michael Johnson…I repeat… The man takes inconsistency to another level.

Jason has won 5 of his last 6 fights with his only loss to wrestling standout and uber athlete Ed Ruth and that was by split decision. The 30 year old Jackson may never be a world champion like Benson. He has a chance, I guess, but the point is that JJ is peaking and Benson is not.

He is actually coming off of a short break after a potential concussion against Michael Chandler just over 3 months ago. I would like to see all fighters coming off of a knockout have to wait at least 6 months before their next fight but at the same time, I get it.

It’s hard to tell people how to make a living.

Keep in Mind:
Henderson was the champ at 155 pounds and this fight will be contested at Welterweight. He will be much smaller and at a speed disadvantage. The only route to victory I see for Henderson here is takedowns and top control.

Ed Ruth barely edged Jackson so that tells me, Bendo will likely come up short.

Pick: Jackson

AJ Mckee Wins Inside the Distance: +185

Caldwell is a tough out, for sure, but he has been tapped in the past and I think there will be some opportunities for AJ from the bottom, top, and back. Once these two start engaging on the mat, it will get hairy.

Caldwell loves a good scramble and I think he might hang himself by doing so.

Whether we see a sub or not, getting nearly 2 to 1 on a finish to happen within 25 minutes is not a bad play, especially considering the level of athleticism each fighter possesses.

Pick: Mckee wins inside the distance

Place Your Bets Now!

In Conclusion

I feel much better about this week’s picks than the previous weekend. We took a shot on 3 underdogs and got shut out. Losing 60/40 or even 70/30 some weeks really stinks but getting shut out really hurts.

Speaking of shutouts, I foresee Jeremy “Don’t call me Jamie” Kennedy as well as Joey Davis handling business in there. Do I think the main event will be a shutout?

No. Caldwell is a tough matchup for anyone because of his wrestling ability. This is a test for AJ but I believe that he is on another level and in a 5-round fight, I really don’t mind chasing the sub or tko win.

As for the co-main event, Jackson’s betting odds haven’t taken off like some expected and for that, he remains affordable at just (-175). I don’t like to bet favorites too much higher than that but I feel like he should be up around (-250), especially in a 3 round fight.

Henderson will have less time to use his experience and smarts and Jackson will have less time he needs to keep his range and defend takedowns.

Get your bets in now!

Mike Pruitt / Author

Mike has been covering sports professionally since 2017 but on the amateur scene for 25 years since when he was 12. Before the internet changed the world, he would keep detailed statistical box scores of NFL and NBA contests, write recaps, and voluntarily commentate games and fights alone in his room. Mike's military experience, Bachelors Degree, and employment thereafter were always rooted in engineering, science, and teaching. Now he enjoys being able to express himself through writing about football, golf, and car racing among other sports but most of all fighting as his life has been rooted in mixed martial arts including competing and teaching for the past 15 years.