These Challenge Competitors Are Still Waiting For A Win

If at first you don’t succeed, try, try again. Or if you’re like a few legendary contestants from The Challenge, try about 12 or 13 more times.

While MTV’s tentpole competition series has produced a collection of decorated victors across 37 seasons (think CT, Darrell and Ashley “Millionaire” Mitchell), it has, all the while, kept more than a few staples of the series from earning championship cash. Call it bad luck or a matter of circumstance, but Aneesa, Tori, Leroy, Jenna and other Challenge linchpins have somehow gone years without standing atop the hallowed podium.

Still, we appreciate their resolve and continue to cheer them on. In fact, we’ve compiled a list of Challenge greats who have come close to victory but have yet to officially taste it:

  • Tori

    The Dirty XXX Rookie of the Year has evolved into one of the most feared competitors in the game, and her staying power on War of the Worlds 2 amounted to one of the most impressive Challenge showings of all time (who could forget when Tori plowed Jenny over in one of the franchise’s most exciting “Hall Brawls”?). Still, Tori proved on Double Agents that she sometimes gets in her own way, especially when she’s not receptive to rookies.

  • Aneesa

    It’s been 19 years since the Real World: Chicago alum appeared on Battle of the Sexes, tried to oust one of the game’s strongest players and instantly became a Challenge legend. And though she’s come close to the title of Challenge champion a few of times, the game always seems to slip through Aneesa’s fingers at the very last second.

  • Kam

    When even CT is scared to square off against you in a “Pole Wrestle,” you know you’re doing something right. Still, Kam, who boasts one of the best elimination-round records of all time, hasn’t managed to make it across the finish line first. Will Double Agents be different?

  • Kyle

    Kyle’s performance on his rookie season served as a blueprint for several seasons since: If you underestimate him, as many are inclined to do, you’re likely to be surprised. Kyle nearly took the crown on Vendettas and Total Madness, but still, his trophy shelf is collecting dust.

  • Cory

    Cory’s Challenge career has been a bit of a checkerboard — sometimes, he’s been blown out before the game really gets underway, and other times, he’s been a real contender, only losing finals by a hair. Will Cory garner a victory on Double Agents — or come close, but no cigar?

  • Jenna

    Jenna, who — in a parallel universe — could have very easily won Exes II or Battle of the Bloodlines, isn’t called Barbie Beast for nothing. She’s got strength to spare on the battlefield and in elimination rounds. In spite of her capacity to perform, though, she has sometimes choked when the pressure’s applied.

  • Leroy

    Leroy put up an impressive rookie season way back on Rivals, making it all the way to the final. He has yet to transcend the distinction of runner-up, though, and he came close to wins on Exes II and War of the Worlds 2. But history has a chance to not repeat itself during the Double Agents final.

  • Nelson

    For someone who nearly beat the heavy-hitting CT on Invasion, Nelson seems like someone who should have likely taken home a win by now. Sadly, he’s often his own worst enemy, and his hot-headed politicking has often kept him from a win. Other times, as was the case with Double Agents, he’s just had bad luck.

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