Michael Jordan's top 10 toughest opponents in his career:

01.) Isiah Thomas
02.) Dominique Wilkins
03.) Joe Dumars
04.) Dennis Rodman
05.) Reggie Miller
06.) Larry Bird
07.) Karl Malone
08.) Sidney Moncrief
09.) Magic Johnson
10.) Patrick Ewing

Honorable Mention:

HM #1 - Ron Harper
HM #2 - Clyde Drexler
HM #3 - Penny Hardaway

Missed The Cut:

01.) Vernon Maxwell, 02.) Mitch Richmond, 03.) Eddie Jones, 04.) Alvin Robertson, 05.) Kobe Bryant

HM #3 - Penny Hardaway - Penny could score against Jordan better than most players but he didn't really present any challenges to Jordan from a defensive standpoint. This rivalry seemed to be on tap in the mid 1990's but never really materialized.  The 1995 Shaq/Penny-led Magic team did beat the Bulls led by the newly-unretired Jordan.  However, the fully re-tooled Jordan-led Chicago Bulls embarrassed the Shaq-and-Penny-led Orlando Magic in 1996 and injuries to Hardaway, soon after, derailed their rivalry and what had looked to be a certain Hall-of-Fame career for Penny.

HM #2 - Clyde Drexler - In the 1992 NBA Finals, Michael Jordan showed that, in terms of all-around basketball ability and willpower, he was a far more superior basketball player to Drexler than many people had long insisted. Drexler had height and had excellent low-post moves for a shooting guard but he seemed to noticeably shy away from challenging Jordan. Drexler's Portland Trailblazers held their own against Jordan's Bulls in many of their battles in the late 1980's and early 1990's. Most forget that in 1991, the year that Jordan's Bulls first won the NBA Finals that it was Portland with the best record in the league and the Blazers had beaten the Bulls twice that year, in convincing fashion, before being surprised by the Lakers in the Western Conference Finals. Talent-wise, Drexler should have been Jordan's toughest match-up but Drexler just didn't seem to raise his game to the next level when playing Jordan. I would have liked to have seen the Bulls and Blazers meet in the NBA Finals in 1991. I think such a meeting may have changed the legacies of Jordan and Drexler as well as their rivalry (or lack thereof).

HM #1 Ron Harper - Before Ron Harper had a career changing injury, he was one of the best shooting guards in the NBA. When his Cleveland Cavaliers were considered title contenders, he regularly faced Jordan on many occasions. Even though he had trouble defending Jordan (like most players), Harper was one of the few players that seemed to be able to score on Jordan with a high degree of success. Jordan had his hands full with Harper who was an extremely talented, all-around guard, who stood as stall as Jordan. In the 1989 season that featured "the shot" by Jordan over Craig Ehlo and the Cavs, the Bulls had lost all of their regular season meetings against the Cavs - in no small part due to Jordan's difficulties in guarding Harper. If Harper had not gotten hurt, a Jordan/Harper rivalry could have been one for the ages.

10.) Patrick Ewing - Although Ewing and the New York Knicks usually came up empty against the Jordan-led Chicago Bulls when it counted most, Ewing did win his fair share of games against Jordan throughout his career - especially in the early seasons. In the late 1980's, the Knicks had established themselves as supposed contenders in the Eastern Conference before Jordan and the Bulls crashed the party with an announcement of their own in the late 1980's. Ewing didn't have much in the way of Hall-of-Fame support to help him as Jordan did. ...but the Ewing-led Knicks were not without their chances against the Jordan-led Bulls. In the 1989 NBA playoffs, the Knicks were the #2 seed in the Eastern Conference before falling to the #6 seeded Bulls and in 1993, the Knicks surrendered a 2-0 series lead against the Bulls and lost 2-4. Ewing never won a title, but many of Jordan's playoff runs for the title included battles with Ewing's Knicks.

09.) Magic Johnson - Though Magic and Jordan didn't play one another very often, they are linked not only through their 1991 NBA Finals appearance together (which the Jordan-led Bulls won), but also by their contrast of styles and a linear passing of the torch so to speak. Even as a rookie, Jordan never hesitated to guard Magic who was considered to be, by far, the best guard if not best player, in the NBA at the time. When Magic and the Los Angeles Lakers repeated as champions in 1988, Magic was considered by many to be the best and most complete player in the NBA. Magic backed this up by a return trip to the Finals in 1989 (a lost to Detroit, possibly due to Magic's injury as well as that of Byron Scott) as well as winning the MVP in 1989 and 1990. While their 1991 NBA Finals showdown was seen as anti-climatic, the real battle that the two NBA legends had between them was that of NBA legacy. Many say that Jordan is the best player of all-time, however, still others say that title is up for debate with Magic being included in that conversation.

08.) Sidney Moncrief - By Jordan's own admission, Moncrief was his toughest defender. Moncrief was a terror on defense and won the first two Defensive Player of Year Awards. Since the award was very new it took some time for it to gain the prestige that it has now and Moncrief probably did not get the respect that he deserved during his era (as evidenced by his Hall-Of-Fame selection taking so long, despite his NBA resume). Moncrief led the Bucks to the Eastern Conference Finals three times in the 1980's but could not get them past the Philadelphia 76ers and Boston Celtics. Eventually, as the Detroit Pistons, and later the Chicago Bulls, emerged, many had forgotten the battles that Jordan had versus Moncrief because they only met once in the playoffs where the stakes were much higher (which Moncrief's Bucks defeated Jordan's rookie-season Bulls 4-1, by the way). Moncrief was a perennial All-Defensive player, including being on the First Team in both of Michael Jordan's first two seasons in the league.

07.) Karl Malone - Malone was one of Jordan's few notable contemporaries that had a winning record against him in the regular season.  Malone even won the 1997 MVP over Jordan, but it didn't make anyone question whether or not Jordan was the best player in the NBA.  Malone led his Jazz teams into back to back NBA Finals losses to Jordan's Bulls in 1997 and 1998.  In 1997, the Jazz seemed to just be happy to be in the NBA Finals.  In 1998, no one really expected the Jazz to win the NBA Finals and that, seemingly, included the Jazz.  Jordan and Malone didn't play each other one on one very often.  The biggest challenge between the men was inspiring their teams.  Malone inspired his Jazz teams to believe that they could win a championship.  Jordan inspired his teams to believe that they would win a championship.  There's a difference.  ...and that was the difference between the two men and thier NBA legacies.

06.) Larry Bird - While Bird and Jordan did not often match up one-on-one, Bird's Boston Celtics were neck and neck with the Los Angeles Lakers for supremacy of the NBA and ruled the Eastern Conference with an iron fist when Jordan came into the league. Jordan once pointed out that he had not forgotten when Larry Bird attempted to show him up during an exhibition game when Jordan was transitioning to the NBA. Jordan's Chicago Bulls were swept in the playoffs in back to back seasons in 1986 and 1987 by Bird's Celtics. It was the 1986 playoffs between their two teams where Jordan's 63 points in a triple over-time game clearly got the attention of Larry Bird, the Celtics, and the entire basketball world. Bird said of Jordan's performance that it was "...God, disguised as Micheal Jordan". A shift in power in the Eastern Conference redirected this rivalry as the Celtics began to decline just as the Bulls began to emerge.

05.) Reggie Miller - Miller was one of the best perimeter shooters that the NBA had ever seen and many thought that we ever would see (unitl Steph Curry came along). Miller's Indiana Pacers met Jordan's Chicago Bulls in the 1998 Eastern Conference Finals with the Bulls taking game #7 after a very hard-fought series. Miller didn't have the all-around game of Jordan, but what Miller did have that many of Jordan's opponents didn't seem to have was consistency. Jordan seemed to be able to shutdown many of his opponents but Miller's style of play, including his ability to move without the ball and his quick release, were formidable tools against even the great Michael Jordan. Like with most of his rivalries, Jordan seemed to get better of his opponents. This rivalry was no different, save for the fact that Miller seemed to be very much in his element playing against Jordan and didn't seem the least bit intimidated by Jordan. Miller thrived in pressure situations and probably had made more clutch shots in the NBA during his era than any other player - except for Michael Jordan.

04.) Dennis Rodman - Rodman was an otherworldly defender and there are some who say that he may have been the most versatile defender of his era, if not the best defender in NBA history. As a member of the Detroit "Bad Boy" Pistons, Rodman rode to fame playing tough defense on the best offensive players in the game, including Michael Jordan. Some of Rodman's defensive techniques against Jordan looked more like football than basketball but they were nonetheless, very effective. In large part to Rodman's meticulous defense, the Pistons beat the Bulls in three straight playoff series. Such physical play from Rodman and other members of the Pistons caused Jordan to evolve his game to adapt to such a physical style of play. Rodman could defend any player on the floor from 1-5 and was one of the few players that had some success guarding Jordan on the perimeter. Rodman's defense impressed Jordan enough that Rodman was along for the ride during Jordan and the Bull's second three championships in the late 1990's after having been a bitter enemy of Jordan and the Bulls in the late 1980's and early 1990's.

03.) Joe Dumars - "Joe D", along with Dennis Rodman and their other "Bad Boy" Pistons teammates helped implement what was then known as the "Jordan Rules" to keep Michael Jordan in check. Dumars, more so probably than any other shooting guard in Jordan's career, had the difficult assignment of trying to guard Jordan one-on-one. Such an assignment was nearly impossible as Jordan proved time after time that an argument could be made that he was the most talented player in NBA history. That said, Dumars seemed to make Jordan work on the offensive end harder than any other player in Jordan's career. Not as versatile a defender as Rodman, but Dumars was an otherworldly defensive player in his own right and along with with Jordan and Rodman, were a part of the power elite among NBA defenders of their era (and possibly all-time). Dumars did have good team support to help him defend Jordan but it cannot be overstated that Dumars was the most effective one-on-one defender that Jordan ever consistently faced in his career. Jordan could score on anyone, including Dumars. ...but Dumars made Jordan work for every single one of those points, like no other.

02.) Dominique Wilkins - Dominique and Jordan were almost neck and neck in terms of scoring in the mid to late 1980's. After winning the scoring title in 1986, 'Nique finished second to Jordan in season scoring average several times. Each night during those seasons, the box score would be stuffed with stats from the two men. Before the Bulls became contenders in the East, the Wilkins-led Hawks looked as if they might be the team that would unseat the Bird-led Celtics, but such a change of power never materialized. During the early parts of their careers, Wilkins gave just as good as he got from Jordan in terms of scoring against one another. Even though the two played technically different positions, they often matched up against one another on the wings. People debated who was actually the better scorer in the mid to late 1980's - Jordan or Wilkins. When Wilkins matched up against Jordan, it was must-see-TV. The Hawks were in decline and the Bulls on the rise when the teams met in the playoffs in the early 1990's. Wilkins seemed to play far more ferociously and with a chip on his shoulder when faced off against Jordan when the pair was younger. Dominique seemed, for some reason, to play a little more tentatively against Jordan after Jordan became regarded as the league's best player and the title no longer up for grabs between the two. ...and Dominique got robbed in the 1988 Slam Dunk Contest against Jordan (...but he'll always have 1985, where he did beat Jordan).

01.) Isiah Thomas - Let's get this out of the way right now. Isiah Thomas was nowhere near the physical specimen of a ball player that Michael Jordan was. Jordan could pretty much score at will against Isiah and play lock down defense on Isiah as well. The reason why Isiah was Jordan's toughest opponent was because, just like Jordan, Isiah had an indomitable will to win. Isiah's basketball I.Q. was as high as any court general ever to step on the hardwood, including Jordan. There was such a psychologically intense battle between Jordan and Thomas that it has resonated between them decades after their retirements. The Thomas-led Detroit "Bad Boy" Pistons including Dumars and Rodman, beat the Bulls in three successive playoffs before the Bulls were finally able to solve the Pistons in the two teams' fourth successive playoff meeting. The feud between Jordan and Thomas has become as immortal as the two men themselves. From Isiah being accused of being the ringleader for "freezing out" Jordan to keep him from starring in the 1985 NBA All-Star game (which Thomas denies) to Jordan (and others) keeping Thomas off of the 1992 NBA Olympic "Dream Team" (which Jordan does admit), the two men will be forever linked. The Detroit Pistons represented the greatest basketball challenge that Jordan ever faced and Isiah Thomas, as captain of those Pistons teams, was the primary reason why. Throughout Jordan's entire career, no other team gave him as many problems as the Isiah-led Pistons.