Bellator 253: Caldwell vs McKee Betting Preview, Odds and Picks

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Darrion-Caldwell-A.J.-McKee

On Thursday, November 19th, Bellator returns to action live from the Mohegan Sun Arena in Uncasville, CT, for Bellator 253: Caldwell vs McKee. This will be the last Bellator show until December 10th as the promotion will go on a two week hiatus partly due to the Thanksgiving holiday on November 26th.

The main event is a featherweight grand prix semifinal match between Darrion Caldwell and the unbeaten A.J. McKee. The co-featured bout is a welterweight clash between Jason Jackson and Benson Henderson. Rounding out the main card is Joey Davis vs Bobby Lee.

The preliminary card will consist of six fights. However, there have been some last minute adjustments to this lineup as two fights have been cancelled due to an injury and a positive test. Originally, this was an 11 bout card, but it’s now only a nine bout lineup.

Bellator betting sites have released odds for the entire Bellator 253 card. Let’s step inside the betting octagon to examine these odds, identify and potential value, and triangle choke these predictions.

Bellator 253 Preliminary Card

The preliminary card for Bellator 253 features six fights, which begins at 4:15PM ET via Bellator online.

Sullivan Cauley vs Jason Markland

  • Sullivan Cauley (-250)
  • Jason Markland (+190)

This fight was originally scheduled for Mark Glover to take on Sullivan Cauley. However, Glover was removed and replaced with Jason Markland. As of this writing, there’s no official word on the change.

Neither man has any significant professional experience inside the cage. They’ve combined for one pro fight. Hardly much to go on considering there’s not a lot of footage for their amateur MMA careers.

Cauley is a training partner and friend of Ryan Bader. He has the makings of a successful MMA fighter, but his ceiling is unclear as of now.

With that said, there’s no reason to go against the oddsmakers here. Take Cauley to win this week and keep an eye on how the promotion books him moving forward.

Sullivan Cauley vs Jason Markland –Cauley (-250)

Kevin Ferguson Jr. vs Kaheem Murray

  • Kevin Ferguson Jr. (-295)
  • Kaheem Murray (+235)

Murray makes his Bellator debut this week after going 1-2 in his last three pro fights. Two of his career losses have come via submission. He last competed in June 2019 where he lost via 3rd round submission. All three of his wins have come via TKO/KO.

Kevin Ferguson Jr., also known as “Baby Slice,” is the son of the late Kimbo Slice and is a heavy favorite for this fight. All of his pro contests have come under the Bellator banner. He last fought 13 months ago and that bout was a NC. All three of his wins have come via stoppage with two by way of submission.

There’s no reason to think that Baby Slice won’t win this fight. He seems to be the better overall fighter and has fought tougher opponents than Murray. I expect Ferguson to get the stoppage win in this contest.

Kevin Ferguson Jr. vs Kaheem Murray –Ferguson Jr. (-295)

Jay-Jay Wilson vs Sergio De Bari

  • Jay-Jay Wilson (-375)
  • Sergio De Bari (+285)

Sergio De Bari makes his Bellator debut this week and enters on a four fight winning streak. He last competed in May 2019 and won via unanimous decision. Three of his five pro wins have come via stoppage with two by way of submission. He’s 2-1 when going the distance.

The undefeated Jay-Jay Wilson is 5-0 with Bellator and also has five stoppage wins including four in the first round. His last fight came in July where he defeated Tywan Claxton via split decision. Wilson is just 23 years old and is evolving into one of the promotion’s brightest prospects.

This matchup favors Wilson because he doesn’t have to worry about facing a pure striker like Claxton. Instead, he can take on someone who also prefers to grapple or find submission holds.

With that said, I am taking Wilson to win this fight via stoppage. I believe he will close the distance, smash De Bari up against the cage and finally get him to the mat where he will lock in a submission hold. Four of Wilson’s five pro wins have come via submission.

Jay-Jay Wilson vs Sergio De Bari –Wilson (-375)

Jaleel Willis vs Mark Lemminger

  • Jaleel Willis (-205)
  • Mark Lemminger (+165)

The first three prelim bouts featured fighters with few bouts on their resume. This one has two MMA vets who each have stepped inside the cage at least 13 times apiece.

Lemminger last competed in August where he lost via TKO due to a doctor’s stoppage. That loss snapped a four fight win streak. He’s 1-1 in Bellator.

Eight of his 11 pro wins have come via stoppage with five by way of TKO/KO. He’s 3-0 when going the distance. Both of his losses have come via TKO/KO.

Jaleel Willis returns to Bellator for the first time in four years. Since then, he spent the majority of his career in LFA. Willis enters on a four fight win streak and last competed in August where he won via unanimous decision. Five of his 13 pro wins have come via TKO/KO. He’s 8-1 when going the distance.

This is an underrated matchup on the preliminary card as both men are capable strikers. However, unless one of them makes a mistake then this fight should go the distance.

Nine of Willis’ 15 pro bouts have gone the distance including four in a row, which he won all four of them. I’m taking Willis to win via unanimous decision over a game Lemminger.

Jaleel Willis vs Mark Lemminger –Willis (-205)

Jeremy Kennedy vs Matt Bessette

  • Jeremy Kennedy (-425)
  • Matt Bessette (+320)

This contest has the largest disparity in betting odds for the entire Bellator 253 lineup.

Bessette is on a two fight win streak after being bounced from the UFC in the summer of 2018 when he dropped two in a row. He’s actually on this third stint with Bellator after first debuting in 2012. Bessette has a 7-2 career record with Bellator and last competed for them in April 2016.

16 of his 24 pro wins have come via stoppage with eight wins apiece for TKO/KO and submission. He’s 8-6 when going the full distance.

Kennedy last competed 13 months ago when he lost in the semifinals of the featherweight tournament for PFL. However, that loss was overturned to a NC after his opponent failed a test. Prior to the NC, he had two wins in a row.

Kennedy also competed in the UFC where he went 3-1. It was a surprise that he left the promotion following his loss to Alexander Volkanovski considering he started off 3-0 inside the octagon.

Eight of his 15 pro wins have come via stoppage with six via TKO/KO. He’s a perfect 7-0 when going the distance.

I’m a bit surprised at how big the disparity is with these betting odds. Bassette deserves a little more credit than being the largest underdog on the card. He does have a solid record with Bellator.

With that said, I am giving the edge to Kennedy in this contest. I like what I saw from him in PFL despite his most recent loss. I think he will have the striking advantage in this bout and that should be enough to get a decision win over Bassette.

Jeremy Kennedy vs Matt Bessette –Kennedy (-425)

Keith Lee vs Raufeon Stots

  • Keith Lee (+255)
  • Raufeon Stots (-310)

This bout is expected to be the featured fight for the preliminary card.

Lee enters this week’s bout having won four straight fights including both of his Bellator contests. He last competed two months ago and won via unanimous decision over Vinicius Zani. Four of his seven pro wins have come via stoppage with three by way of TKO/KO. He’s 3-0 when going the distance.

Stots makes his third trip inside the Bellator cage where he’s 2-0 so far. He last competed in July and won via 3rd round submission over Cass Bell. He’s currently on a six fight win streak. Seven of his 14 pro wins have come via stoppage with four by submission. He’s 7-0 when going the distance.

Stots’ lone loss came against Merab Dvalishvili back in June 2017. He would love to get a rematch against Dvalishivili, but Merab is with the UFC and rising up the ranks in the bantamweight division.

I see this fight going the distance (-215) as Lee has never been stopped in a pro bout. Furthermore, 10 of their 25 total bouts have gone the distance.

As for the winner, I am taking Stots to pick up the unanimous decision win which offers the best value for this bout (-115). He’s the better overall fighter and on the rise in Bellator.

Keith Lee vs Raufeon Stots –Stots (-310)

Fight goes to a decision (-215)

Stots wins via decision (-115)

Bellator 253 Main Card

The main card for Bellator 253 features three fights with a start time of 7PM ET on CBS Sports Network and DAZN.

Joey Davis vs Bobby Lee

  • Joey Davis (-400)
  • Bobby Lee (+325)

The opening bout of the main card features two prospects that are both solid fighters. Despite Lee’s four pro losses, he has a lot of potential.

Lee has won two straight fights and is the current Cage Fury welterweight champ. He also spent a few years in LFA where he had some success as well. His last bout came in two months ago where he beat Michael Hill via unanimous decision.

Eight of his 12 pro wins have come via stoppage with six by way of submission. He’s 4-2 when going the distance.

Joey Davis has spent his entire pro career with Bellator and has gone undefeated since debuting in August 2016. He’s won three straight fights via TKO/KO. In fact, five of his seven pro wins have come via TKO/KO and all five were in the first round. He’s 2-0 when going the distance.

I think this bout is going to end inside the distance (-210). Combined, 15 of their 23 pro fights have ended inside the distance. Davis has gone the distance in just two fights.

As mentioned, five of Davis’ pro wins have come in the 1st round of a fight. Two of Lee’s four losses have come via stoppage. I see Davis picking up the stoppage win in this contest (-115) most likely via TKO/KO. His striking skills are notably better than Lee’s.

Joey Davis vs Bobby Lee –Davis (-400)

Fight ends inside the distance (-210)

Davis wins inside the distance (-115)

Ben Henderson vs Jason Jackson

  • Ben Henderson (+150)
  • Jason Jackson (-170)

The veteran Benson Henderson enters as a sizable underdog in the co-main event of the night. Henderson last fought in August and lost via 1st round KO to Michael Chandler. The loss snapped a four fight win streak and was the second defeat to Chandler.

For the first time in eight fights, Henderson is going back up to welterweight after competing as a lightweight. However, the former champ is actually excited about being able to fight at 170 pounds:

“So, yeah, definitely I’m ready. Being at 170 makes it just that much better for me so that I can concentrate on the fight. I can concentrate on my opponent. I don’t have to worry and obsess over how many calories I’m eating. When I’m eating my calories, the amount of protein I’m eating … the hard part for me is getting down the weight. So taking that out of the equation, I can just worry about Jason Jackson.”

14 of his 28 pro wins have come via stoppage with nine by way of submission. He’s 14-5 when going the distance.

Jackson rides in on a two fight win streak after dropping his Bellator debut to Ed Ruth 13 months ago. He’s won five of his last six contests and is improve inside the cage. However, the biggest knock against Jackson is the fact that he’s never really fought anyone the caliber of Henderson.

Ed Ruth was probably the most accomplished fighter that Jackson has faced, if you don’t count a young Colby Covington in June 2012. And, Ruth ended up defeating Jackson via split decision.

Seven of his 12 pro wins have come via stoppage with four by way of TKO/KO. He’s 5-2 when going the distance.

Henderson might not have the power or speed that he used to possess, but he’s still very capable of defeating Jackson. In fact, I believe he will outclass Jackson this week largely due to his experience and savviness.

I see this fight going the full 15 minutes (-265) as these two men have combined to go the distance in 26 of 53 total fights. Henderson has gone the distance in seven of his last 10 bouts, while Jackson has gone to the judges in four straight fights including all three of his Bellator bouts.

Take Henderson in an upset! His moneyline offers the best value for this contest.

Ben Henderson vs Jason Jackson –Henderson (+150)

Fight goes the distance (-265)

Henderson wins via decision (+235)

Darrion Caldwell vs A.J. McKee

  • Darrion Caldwell (+205)
  • J. McKee (-245)

The main event of the night is a semifinals bout in the featherweight grand prix. McKee enters as a sizable favorite and won in his first tournament fight via 3rd round submission over Derek Campos. Caldwell defeated Adam Borics via 1st round submission.

These two might have a similar number of pro bouts, but Caldwell is seven years older and has been with Bellator since early-2014. He’s 12-3 in Bellator and last fought in January when he beat Borics. Caldwell has won two straight contests.

Eight of his 15 pro wins have come via stoppage with six by way of submission. He’s 7-1 when going the distance. Caldwell is 6-0 as a featherweight in Bellator and 8-0 at this weight class in his career.

McKee is one of Bellator’s best young fighters. He’s spent his entire pro career with Bellator since debuting in the spring of 2015. This will be his first fight of 2020 as he hasn’t fought since December 2019 when he defeated Derek Campos.

McKee will put his 16 fight win streak on the line, which is not only the longest active streak in Bellator, but it’s also the longest in the promotion’s history. It’s also tied for the longest winning streak with one promotion. Anderson Silva also accomplished this feat with the UFC.

11 of his 16 pro wins have come via stoppage with six by way of TKO/KO. He’s 5-0 when going the distance. Those 11 stoppage victories are the 3rd most in Bellator history. His five submission wins are the most in the history of Bellator’s featherweight division.

With all of that in mind, I am picking A.J. McKee to win this fight via decision (+155). I think Caldwell’s grappling and striking will keep him in this bout for the full distance (-155). However, I do believe McKee will edge out Caldwell in what will be an exciting matchup.

I think McKee has been forged in tough battles against other veteran Bellator fighters prior to this tournament. His athleticism and wrestling background will be too much for Caldwell to overcome. This is going to be a solid win for McKee in a strong main event tournament bout.

Darrion Caldwell vs A.J. McKee –McKee (-245)

Fight goes the distance (-155)

McKee wins via decision (+155)

Full Bellator 253 Card

  • Darrion Caldwell (15-3) vs A.J. McKee (16-0)
  • Ben Henderson (28-9) vs Jason Jackson (12-4)
  • Joey Davis (7-0) vs Bobby Lee (12-4)

Preliminary Card

  • Keith Lee (7-3) vs Raufeon Stots (14-1)
  • Jeremy Kennedy (15-2) vs Matt Bessette (24-9)
  • Jaleel Willis (13-2) vs Mark Lemminger (11-2)
  • Jay-Jay Wilson (6-0) vs Sergio De Bari (5-1)
  • Kevin Ferguson Jr. (3-2) vs Kaheem Murray (3-3)
  • Sullivan Cauley (0-0) vs Jason Markland (0-1)
Rick Rockwell

As a longtime freelance writer, avid sports fan, former athlete, and experienced sports bettor, Rick Rockwell has risen up the ranks at GamblingSites.org to become the self-professed "King of the Blog" in his first year with the site. ...

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