The Chicago Bulls faced the Charlotte Bobcats with Michael Jordan sitting beside Scottie Pippen. On one play as he delivered a marvelous no look pass to Carlos Boozer, Rose tossed a look at the two greatest Bulls as though to say, "I have nothing but respect for you guys; you are the history of the Bulls, but I am the future." Judging by the impressed expressions they returned on several plays they agreed.

It brought to mind a question I'd been asked once, how effectively could Michael Jordan guard Derrick Rose? My initial response was, "Come on! We're talking about MJ here!" However, after I gave it some thought and a little research, the question is more difficult to answer that than I initially thought.

The most difficult thing to gauge statistically on a basketball court is speed. Basketball speed is not the same as football seed. You're not going to be able to determine how well someone could guard someone by just looking at a generic "speed" factor. You have to see how that translates to speed on the court. When you're comparing players from different eras, that's just impossible.

However, what you can do is see how the players compared against "like" players in their own eras. I thought I'd take a look at both sides of the match up and see how players compared to players from their own era that are similar to the other.

First, I took the D-Rose side. I considered which players from the Jordan era had the same capabilities offensively that Rose has, incredible speed, killer crossover, and ability to drive to the basket and score even if there's contact. He also needed to have the same ability that Rose has carved out for himself to shoot from the three. The closest I could think of was Allen Iverson.
He shot .313 from the three and averaged 26.7 points for his career. Over the two years that overlapped with Jordan, he averaged 23.5 and 22 points to go with 7.5 and 6.2 assists. Iverson was, like Rose, as quick to the basket as anyone in his era. In style of play and overall production he's about as close as you can get to Rose among players who went up against Jordan.

I will grant that the problem here is Iverson was a point guard while he and Jordan were both in the league. However, Jordan was often assigned the job of defending the other teams toughest players, and at the very least he would have been offering some help defense on Iverson.

I also acknowledge that the timing was in Iverson's favor. He was in his first two seasons and Jordan was in his last two with the Bulls. His speed wasn't what it was when he was younger. He was however still first team on the NBA All-Defense team. In sum, I recognize that while it's not a pure comparison, it's just as close as I can come.

As far as any guard against the Bulls in the Jordan era though, it is possible that no one was as successful as Iverson. "The Answer" averaged 27 points and five assists in his seven games against Jordan. As far as what I can find, no guard had more success against the Bulls than Iverson.

His 44 is tied with Reggie Miller's for most by a guard in the Jordan era. In fact, of the top 50 performances against the Bulls by guards in the Jordan era, Iverson owns four of them. The only other player who can make that claim is Miller, who had five times as many total games against Jordan. In other words, not only can it be argued that Jordan struggled (at least in help defense) guarding Iverson, but that he was the only player that Jordan struggled against consistently.
On the other side, I considered which player most resembles the style of defensive play that Jordan has. This was a little easier to come up with, as the player that resembles him in physical stature and who modeled his style after Jordan, Kobe Bryant, is pretty obviously the best player to consider.

This year Derrick Rose has elevated his game to a higher level. That's a tough statement to argue with. In his two games against the Lakers, D-Rose has averaged 29.5 points, 8.5 assists and five rebounds. Particularly in the last game the Lakers perennial All-Star took to guarding Rose at the end of the game and Rose consistently scored on him.

In the end I have to say that even Michael Jordan, one of the greatest defenders of all time, would struggle to guard Derrick Rose one on one. There isn't one player in the NBA right now who can shut Rose down one one one and it's hard to think of anyone historically who could either.