Brian Kelleher (+235) vs. Ricky Simón (-290)
Weight Class: Featherweight (145 lbs)
I love lowkey fights with some backstory and hype behind them. With Ricky Simón and Brian Kelleher finally set to throw down at UFC 258 following multiple cancellations, that’s exactly what we’ll have. The two have had fights with each other cancelled twice due to COVID-19; once due to a positive test for one of Simón’s corner men, as well as a more recent cancellation after Kelleher himself came down with the virus.
After Kelleher tested positive for the virus, Simón secured an impressive second round arm triangle against UFC newcomer Gaetano Pirrello. He then proceeded to call out Kelleher in his post-fight interview. “I’m on a quest to send Boom Boom Baggins back to The Shire,” he said. “Simon says you lucked out,” Kelleher then replied via Twitter, having earlier called for the fight himself.
So, when this one finally gets underway, it should be quite interesting. The fight has also been moved to the main card after a bout between Jim Miller and Bobby Green was scrapped.
As far as recency goes, both Kelleher and Simón have had plenty of success. Brian Kelleher had a career year in 2020, going 3-1 with all three wins coming via stoppage. This includes a first round guillotine submission of Ode Osbourne at UFC 246, a come from behind flush knockout of Hunter Azure and most recently, a first round guillotine submission against Ray Rodriguez. Rodriguez made his UFC debut on short notice, as did Simón’s last opponent, who he also submitted.
Kelleher’s lone loss was against Cody Stamann at UFC 250, which is very relevant for this fight. Ricky Simón employs heavy wrestling and is a take down machine. Kelleher does have a fantastic guillotine, but Simón keeps his head very high, which will negate that threat.
If Simón is able to implement a similar game plan to that of the one he employed against Ray Borg, this is his fight to lose. Kelleher has a chin and may have the edge in the technical striking department, but he doesn’t have flush knockout power. The Azure KO was excellent, but Azure was also repeatedly making the same exact entry while leaving himself vulnerable. Kelleher seemed to get a read on his attacks and eventually counter, securing a solid knockout.
I just don’t see a path for anything similar here. Simón should be able to secure multiple take downs and win this fight with heavy wrestling, or clinch work. Ricky Simón has a solid submission game himself, but I do think that Kelleher is crafty enough to avoid getting subbed. Ultimately, I see Simón racking up at least half of each round in top control.
Betting wise, I do have 1u on Ricky Simón by points at (-125). This works great as a parlay piece, as does the moneyline.
Prediction and play: Ricky Simón by decision (-125)
More UFC 258 Breakdowns:
Rodolfo Vieira vs. Anthony Hernandez