One of former UFC superstar Nate Diaz’s best combat sports highlights came against Kurt Pellegrino in Broomfield, CO.
Nate Diaz was known as Nick Diaz‘s younger brother during the infancy of his UFC career. But at a UFC Fight Night event in 2008, Diaz carved his own path in what’s considered the ‘baddest’ moment of his promotional tenure.
Diaz and Kurt Pellegrino squared off at a UFC Fight Night headlined by Kenny Florian vs. Joe Lauzon in Broomfield, CO. After winning The Ultimate Fighter 5, Diaz was in the big spotlight as he went on an impressive win streak to begin his UFC career.
During his time in the UFC, Diaz has earned memorable wins over Conor McGregor, Anthony Pettis, and Donald Cerrone. But his win over Pellegrino solidified him as a star for the UFC to help continue to grow its brand off of.

Nate Diaz flipped off Kurt Pellegrino as he tapped him with a nasty choke
Diaz and Pellegrino had some beef entering their lightweight bout in April 2008. After a slow start for Diaz against Pellegrino in the opening minutes, he quickly found his momentum in Round 2 from bottom position.
As Diaz trapped Pellegrino in a triangle choke, and as Pellegrino appeared close to tapping, Diaz flexed and flipped off Pellegrino mid-submission just before the fight was called off. Diaz walked away with a ‘Submission of the Night’ post-fight performance bonus for his victory.
You can watch the full sequence below.
Nate Diaz vs Kurt Pellegrino https://t.co/rY2QjccbYK
— MMA Gone Wild🥋 (@mmagonewild) August 26, 2019
Nate Diaz teased a UFC return after getting revenge over former BMF rival
Diaz went on to eventually fight for the UFC lightweight title against Benson Henderson four years after the Pellegrino win, losing by unanimous decision. After an up-and-down run in the UFC, a short-notice upset win over McGregor skyrocketed Diaz’s stock to new heights.
Diaz parted ways with the UFC following a win over Tony Ferguson in the UFC 279 main event in 2022. But after a boxing loss to Jake Paul and a win over former BMF rival Jorge Masvidal, Diaz could potentially be on the way back to the Octagon in 2025.
Diaz entertained a potential return to the UFC in a recent interview, but cited the UFC’s lack of big-name stars as a main reason he’s hesitant to return to MMA. He wants to make a run to a UFC title, despite losses in three of his last five MMA outings.
A trilogy fight with McGregor is one such option that could lure Diaz back to the Octagon. But that option is off the table, at least temporarily, after McGregor teased retirement from MMA at a recent Bare Knuckle FC press conference.
In either case, Diaz remains a top name in combat sports and would likely make big bank in any combat sports venture. Don’t be surprised if the Stockton star returns to the Octagon this summer as he looks to potentially contend for a title.