While Islam Makhachev is the most accomplished champion in UFC lightweight history, many believe his bid to claim two-division glory would be anything but easy.As the Dagestani gears up to challenge Jack Della Maddalena for the welterweight title at UFC 322, Robert Whittaker seems to be among those doubting the former pound-for-pound king's ability to get the job done.During a recent segment of the MMArcade podcast, the former middleweight champion claimed that there was no significant skill disparity between the fighters. 'The Reaper' also seems convinced that Maddalena has credible enough jiu-jitsu skills to curb Makhachev's takedown threat.The Australian gets Whittaker's nod in the striking department as well. 'The Reaper' believes the welterweight kingpin's superior boxing skills would help him tip the fight in his favor if it ends up having prolonged stretches of stand-up like in Makhachev's first fight with Alexander Volkanovski:"From the things that I remember seeing in the Volk[anovski] fight, their first pairing. I just see. I see the fight potentially going that way, but I think Jack is in a better position to take advantage of the things that Volk couldn't. I think he has got better hands, especially over five rounds, with longer arms and reach. Especially considering [that] Islam is going to be trying to close that distance and get closer. Jack's tight fighting is so high level."The New Zealander also highlighted that Makhachev carried all the risk in the fight, considering he has more to lose as one of the UFC's top stars:"External effects are a side as well. Jack has nothing to lose. I think Islam has everything to lose. He is the hottest prospect right now."Check out Robert Whittaker's comments on Jack Della Maddalena vs. Islam Makhachev below:Top welterweight grappler picks Jack Della Maddalena over Islam MakhachevOne of the top grapplers at 170 pounds, Sean Brady, believes Islam Makhachev would have a hard time imposing his wrestling game on Jack Della Maddalena when they meet in the octagon.During a recent episode of UFC Unfiltered, the No.2-ranked welterweight contender picked Maddalena to retain the belt, claiming that it was a daunting task to hold and control the Australian on the ground:"I think it’s a lot tougher of a fight for Islam than people are giving Jack credit for. Jack’s very hard to hold down. He’s a big boy, hits like a freight train, has knockout power, and he showed, getting someone down doesn’t mean d**k. Can you hold them down? Jack’s really good at creating scrambles, getting back to his feet, separating hands, and we’ve seen that with Belal [Muhammad]... If I had to pick, and I know Jack would be the underdog, I would pick Jack."