Toronto Raptors — Tracy McGrady
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After MJ and Kobe, T-Mac may have been the closest thing to either of those two. Of course, he failed to stay healthy for long stretches of his career. With that said, McGrady’s talent was through the proverbial roof. You were looking at a guy close to 6-foot-9 with incredible athleticism, ball skills, and the ability to put the ball in the hoop.
It was highly enjoyable watching McGrady star with cousin Vince Carter in Toronto for the Raptors. However, the franchise elected to let McGrady walk — executing a sign-and-trade with Orlando for a future draft pick. Ultimately, McGrady developed into a Basketball Hall of Famer. He was excellent with the Magic, making seven-straight All-Star appearances and seven-straight all NBA teams.
Milwaukee Bucks — Dirk Nowitzki
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Oh boy, this was a mistake — no matter how you slice it. Milwaukee took Dirk with the No. 9 overall pick in the 1998 NBA Draft. Along with Steve Nash, both were sent to Dallas on draft day. Nowitzki not only led Dallas to an NBA Title, but he also made 14 All-Star appearances. He revolutionized the power forward spot as one which now included long-range shooting. Oh — and Dirk is arguably the best foreign-born player in the history of the league.
Charlotte Hornets — Kobe Bryant
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Credit Jerry West for having the foresight to see what a special player Kobe Bryant would turn out to be. Hailing from Lower Merion High School in the Greater Philadelphia area, the Lakers knew that they wanted Bryant badly. In a deal with Charlotte, LA traded fan favorite/All-Star center Vlade Divac for Bryant. In the process, this opened up the requisite cap space for the Lakers to sign Shaquille O’Neal. Talk about a banner day for the franchise.
We all know about Kobe’s story. He’s the closest thing to Michael Jordan — and is undoubtedly a top-10 player all-time. He helped the Lakers win five NBA Championships, and he made 18 All-Star appearances in the process.
Philadelphia 76ers — Charles Barkley
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Barkley was a beast for the 76ers. During his time in Philly, Sir Charles had six All-Star appearances. As such, it was a bit perplexing as to why the Sixers decided to ship Barkley to Phoenix right in the middle of his prime. Barkley was a bit of a controversial player — though he didn’t necessarily do anything ‘that bad’ which would warrant him being shipped out for a package including Jeff Hornacek, Andrew Lang, and Tim Perry.
The Alabama native went on to make five more All-Star appearances for the Suns. This included being the league’s MVP in 1993, and leading the Suns to the Finals during the same year. Surely Philly wishes they would’ve kept Chuck in The City of Brotherly Love.
Los Angeles Lakers — Shaquille O’Neal
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The biggest ‘what if’ centers around Shaquille O’Neal and the Los Angeles Lakers. Let’s get this out of the way: Shaq and the late Kobe Bryant is the best tandem in the history of the NBA. We’re willing to bet that there will never be another tandem as good as these two. They won three-straight titles with absolute ease. Behind the scenes, we learned about the quarrelling between the two stars.
Ultimately, the Lakers kept the younger Bryant — and jettisoned Shaq to Miami for a package centered around Lamar Odom. Kobe won two more titles for the Lakers, and Shaq helped Miami win one, as well. Still, it’s a regret that the two couldn’t make it work. There’s a scenario in which the Lakers win six to seven titles with the dynamic duo.
Washington Wizards — Ben Wallace
The Wizards have proven to be a bit inept as it pertains to personnel decisions. Case-in point, the career of Ben Wallace. The undrafted big man played for three seasons in the nation’s capital. He put up rather uninspiring numbers — though he did develop into a promising player from a defensive standpoint. It didn’t matter to Washington, as he was shipped out (despite averaging 2.0 BPG) for someone named Isaac Austin
Isaac Austin was a journeyman who featured for 13 different teams in three different continents. Wallace — on the other hand — was just recently inducted into the Basketball Hall of Fame after developing into one of the best defenders in modern history. He won the Defensive Player of the Year award on four separate occasions despite generously being listed at 6-feet-9. Many also believe Wallace is the best undrafted player in the history of the league.
Houston Rockets — Elvin Hayes
Elvin Hayes was a transcendent player during his prime. He bounced back and forth between the Power Forward/Center spot. This sort of versatility was highlighted by Hayes’ ability to score from anywhere in the paint. He was downright dominant on the glass (career averages of 12.5 RPG and 2.0 BPG). Simply put, he was an elite player.
Despite making the All-Star team four-straight years for the then-San Diego Rockets, they decided to trade Hayes — at age 27 — for a guy named Jack Marin. Marin was a two-time All-Star, to be fair. However, Hayes is an NBA all-time great. In the wake of trading Hayes to the Washington Bullets, Hayes made eight-straight All-Star appearances. He also led the team to an NBA title.
LA Clippers — Adrian Dantley
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The Clippers’ franchise once resided in Buffalo. Adrian Dantley — a long time NBA fixture (as a player and coach) — played his rookie season for the then-Buffalo Braves. Despite averaging 20.3 PPG, Dantley (the NBA Rookie of the Year) was discarded along with a teammate for big-time scorer Billy Knight. It was a calculated gamble by the Braves, and one which ultimately didn’t pan out.
Dantley went on to become a scoring machine. He averaged nearly 27 PPG as a second-year player. Throughout his career, Dantley made six All-Star appearances. He also led the NBA in scoring on two separate occasions. As has long been the case with the Clippers, they simply cannot get out of their own way.
Memphis Grizzlies — Pau Gasol
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When this trade was first executed, it appeared as if the Grizzlies got completely fleeced by the Lakers. Then-Memphis executive (and former Lakers’ legend) Jerry West sent Pau Gasol to Los Angeles for Kwame Brown, Javarris Crittenton, Aaron McKie, two first-round picks, and the rights to a doughy second-round pick named Marc Gasol.
Pau teamed with Kobe to help the Lakers win two NBA Championships. Pau will likely go into the Basketball Hall of Fame as a Laker. This wasn’t ideal for Memphis. However, Marc ended up becoming one of the franchise’s most important players. He was a true stalwart for over a decade — earning All-Star appearances and All-NBA denotations.
Phoenix Suns — Gail Goodrich
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Gail Goodrich grew up in Los Angeles, and starred for John Wooden at UCLA. As such, it only made sense for him to one day make his way back to Los Angeles to star for the Lakers. Ironically enough, the rival Phoenix Suns made this dream into reality.
Goodrich came to the Suns (from the Lakers) in the expansion draft. After making the All-Star team and developing into a core member of the team, Phoenix turned around and traded Goodrich…back to the Lakers. Yes, it doesn’t appear to make much sense to us, either. From there, Goodrich made four All-Star teams with his hometown Lakers. He also helped them win an NBA Title playing alongside Jerry West.
New York Knicks — Gene Shue
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Shue spent a whopping 45 years in the sport — first starting as a player and then eventually becoming a coach/front office executive. The Maryland native played for the Knicks before being traded to the Fort Wayne (now Detroit) Pistons. Of course, knowing the Knicks’ luck, this was an ill-fated move.
Shue’s ability to entertain with the ball off the dribble was on full display in the Motor City. He made five-straight All-Star appearances with his new team. Of course, when the Knicks traded back for him, Shue never made another All-Star appearance.
Denver Nuggets — Carmelo Anthony
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We all remember this trade. Though Denver takes the blame for essentially trading Anthony, it wasn’t the Nuggets’ fault. The East Coast native wanted to go back home and play for his hometown Knicks. Obliging with the request, Denver’s return package (Danilo Gallinari, Raymond Felton, Wilson Chandler, Timofey Mozgov, and a first-round pick) ended up being very underwhelming.
While Anthony never won anything of consequence in New York, Denver traded away a transcendent player and got little in return. Anthony would’ve gone down as the best player in the history of the Nuggets’ franchise. There’s also a plausible scenario in which they’d be able to get him help down the line. While Anthony wanted out, Denver could’ve at the very least gotten a better group of assets back.
Orlando Magic — Chris Webber
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People might not realize that the Orlando Magic had drafted Chris Webber with the No. 1 overall pick in the 1993 NBA Draft. Imagine — a young frontcourt featuring Webber and Shaquille O’Neal playing alongside each other. Instead, the Magic’s front office wanted to pair O’Neal with a young guard named Penny Hardaway. Webber was traded to Golden State for Hardaway and three (!) first-round picks.
Hardaway was an elite talent. However, the Magic never could get over the hump in large part due to Hardaway’s inability in staying healthy. Webber, on the other hand, developed into one of the NBA’s most versatile big men. He was automatic from mid-range, could score with either hand in the post, and was a fantastic passer of the basketball. Webber made five All-Star appearances before retiring. We’re always left with the ‘what if’ situation as it pertains to Webber, Orlando, and the potential pairing with Shaq.
Detroit Pistons — Bill Sharman
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The then-Fort Wayne Pistons had the rights to Bill Sharman. As many recall, Sharman was a shooting guard in every sense of the term. He’d launch shots from anywhere — and would hit them with relative regularity compared to his peers. The Pistons took him in a dispersal draft after Sharman’s original team (Washington Capitols) disbanded. However, this was a short stay — as the Pistons dealt Sharman to the Boston Celtics.
Boy, did this turn out to be a major mistake. Sharman not only became a 8-time All-Star/face of the NBA, but he also helped the Celtics win four NBA Championships. Suffice it to say, but we think the Pistons regret making this move.
Boston Celtics — Joe Johnson
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Johnson was taken by the Celtics out of Arkansas with the No. 10 overall pick in the 2001 NBA Draft. Unfortunately for Johnson, he wasn’t given much of an opportunity to showcase his skills. He played one season with Boston before being traded to the Phoenix Suns in a deal involving NBA journeymen (Rodney Rodgers, Randy Brown, Tony Delk, Milt Palacio).
Remember, this is a player who wanted to prove himself — as well as justifying his draft selection. Getting to Phoenix was the best thing for Johnson’s career. He was given the time to actually develop as an NBA player. Atlanta saw the potential — and inked him to a massive multi-year deal. Seven All-Star appearances later, and the Celtics certainly made a big mistake in giving up on Johnson a year after drafting him.
Atlanta Hawks — Bill Russell
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There was a time — albeit a brief one — when Bill Russell wasn’t destined to wear the iconic green and white we’ve come accustomed to see him in. The St. Louis Hawks took Russell with the No. 2 overall pick back in 1956. The Celtics desperately wanted Russell to anchor their defense, and the Hawks had interest in Boston’s veteran center Ed Macauley (a 6-time All-Star in his own right).
The rest, as they say, is history. Russell became arguably the most dominant defensive big man of all-time (not to mention a top-10 player ever). He made 12 All-Star appearances — and helped the dynastic Boston Celtics win an astounding 11 titles.
Brooklyn Nets — Bernard King
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The New York playground legend actually began his career with the Nets. King averaged 24.2 PPG as a rookie in New Jersey. After another year in which he averaged over 20 PPG, King was unceremoniously jettisoned to the Utah Jazz. The Nets were said to be in the market for more size — which ultimately (and shockingly) made King available.
After two good seasons in Golden State (preceded by one bad year with the Jazz), King ended up back home in the Garden with the Knicks. The Nets watched as King made four All-Star Game appearances. This included multiple All-NBA denotations, and a scoring title.
Miami Heat — Glen Rice
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It’s always perplexing when rebuilding teams trade away young, talented players (on manageable contracts) for expensive veterans. Many times, it’s a huge gamble which rarely pays off. Drafted by Miami, Rice established himself early on as a very productive gunner from three.
Ultimately, the Heat moved on from Rice in a deal which netted them Alonzo Mourning. Miami witnessed Rice flourish in Charlotte. He made three-straight All-Star appearances, and by that point was among the best shooters in the NBA.
New Orleans Pelicans — Chris Paul
“The Point God” was a revelation in New Orleans. Paul quickly became one of the NBA’s best players (regardless of position). As he racked up the personal accolades, New Orleans couldn’t get over the hump as a legitimate playoff contender. Knowing how difficult it would be to re-sign Paul, New Orleans opted to send him to the Lakers in what was a total blockbuster.
That trade was nixed over fairness issues — and Paul was rerouted from the Lakers to the neighboring Clippers. Even today in his late 30’s with the Suns, Paul continues to perform at an extremely high level. New Orleans should’ve done anything in its power to keep Paul home. He’s undoubtedly headed for the status as a top-five PG to ever play the game.
 Chicago Bulls — LaMarcus Aldridge
This is a trade the Bulls dearly regret making. LaMarcus Aldridge likely will become a Hall of Famer. The sweet-shooting big man was a walking double-double for nearly a decade. He scored in the paint, protected the rim, and was nearly automatic from midrange. When taken No. 2 in the 2006 NBA Draft, it appeared as if the Bulls had a real talent on their hands.
Instead, he was flipped to Portland for Tyrus Thomas (the No. 4 pick) and a fringe prospect named Victor Khryapa. Aldridge made five All-NBA teams, seven All-Star appearances, and was one of the greatest big men of his generation. Tyrus Thomas was a freak athlete — though lacked the collective tools to stick in the league. He still is considered to be one of the bigger busts over the last 20 years.
Sacramento Kings — Tiny Archibald
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It doesn’t matter which era we’re in — or where the team is located. No matter what, the Kings will invariably self-sabotage themselves with boneheaded personnel moves. The jury is still out on the Domantas Sabonis/Tyrese Haliburton trade. However, we can attack the Kings for trading Tiny Archibald in the middle of his prime.
Why trade a multi-time All-Star (not to mention one of the league’s most popular players) at age 28 for two picks and two underwhelming players? It doesn’t make much sense to us, either — especially when Archibald made three more All-Star appearances post-trade.
San Antonio Spurs — Kawhi Leonard
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This is a mixed bag when it comes to Kawhi and the Spurs. On one hand, the franchise gets a ton of credit for having the foresight to trade George Hill for his draft rights. Leonard was picked in the middle of the first round, and ended up becoming one of the NBA’s best players. He led the Spurs to a title, and was even pegged as the Finals’ MVP.
However, weird issues popped up with Leonard and his health. There was a lack of transparency coming from both camps. Eventually, it got to a point where Leonard wanted out of San Antonio. He was flipped to Toronto — where the Raptors ended up winning the NBA title (with Leonard leading the way). The Spurs certainly got a lot from the California native. However, there’s an alternate universe where he’s still ‘the man’ in San Antonio.
Dallas Mavericks — Jason Kidd
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This one hurts. Kidd was drafted out of Cal by the Mavericks. The Oakland native was assumed to be the future face of the franchise. Kidd was a very good athlete buoyed by a strong work ethic, a flashy floor game, and an unbelievable feel for the sport from a passing standpoint. Despite being an All-Star starter in his second NBA season, Dallas gave up on Kidd — shipping him to the Suns over what many reported as issues between Kidd and the coaching staff.
What a mistake that turned out to be. Kidd made six All-Star Game appearances with both the Suns and Nets. He led the Nets to the NBA Finals, and was universally regarded as one of the best players in all of basketball for a long time. While he eventually made his way back to Dallas at the tail-end of his career, the Mavericks certainly wished he would’ve stayed with them during the entirety of his prime.
Indiana Pacers — Alex English
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English was a walking bucket for the duration of his career. The 6-foot-8 SF out of South Carolina could get any shot he wanted, and was undoubtedly one of the most prolific scorers throughout the 1980’s. After English failed to make an impact with the Milwaukee Bucks, Indiana took a chance on him with a short contract. Immediately, English exceeded expectations — averaging 16.0 PPG as a third-year guy.
In his fourth season (second with the Pacers), Indiana decided to surprisingly deal English to Denver for a guy (George McInnins) who’s best play was behind him. This proved to be a massive mistake. Over the last decade with the Nuggets, English made eight All-Star appearances. He led the league in scoring once, was a three-time Second Team All-NBA selection, and averaged at least 25.0 PPG in eight-straight seasons.
Oklahoma City Thunder — James Harden
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The upstart Oklahoma City Thunder had cultivated a potential dynasty based upon shrewd personnel decisions. The Thunder had the opportunity to lock up Kevin Durant, Russell Westbrook, and James Harden all to long-term deals. As those three entered their proverbial primes, you’d guess that OKC would run the NBA for the foreseeable future.
Instead, OKC worried about the luxury tax — which led the Thunder to choosing Serge Ibaka over Harden. After Harden turned down multiple contract extensions, he was traded to Houston for Kevin Martin, Jeremy Lamb, and two first-round picks. One of those picks turned out to be Steven Adams. OKC never won a title, the big-two of Durant and Westbrook broke up, and the franchise is now in a total rebuild. Had OKC splashed a bit more cash to keep Harden in the fold, it’s hard to imagine that group not winning at least one title.
Golden State Warriors — Robert Parish
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The Hall of Fame center hailing from Louisiana was at one time a member of the Golden State Warriors. Few remember this period based upon Parish’s success with the Celtics. Regardless, Parish spent four seasons in the Bay Area. After two-straight seasons in which he averaged a double-double, Parish was traded to Boston (along with a first round pick) for two other first round picks. The pick Boston received ended up being Kevin McHale. The rest, as they say, was history.
Parish was a shot-blocking force in the paint for Boston. Aside from nine All-Star appearances, he was integral in Boston winning four NBA Championships. In the process, Parish developed into arguably a top-10 center all-time. Surely, the Warriors regret making that move.
Minnesota Timberwolves — Kevin Garnett
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Rarely does it end well when you trade the face of your franchise. Minnesota has been competitive as an NBA franchise for roughly one stretch — and that coincided with Kevin Garnett being “the man” in the Twin Cities. Garnett’s length, competitive nature, and skill level allowed for him to become the best player in the history of the franchise. He was ferocious defensively — and was nearly automatic with his patented baseline jumper.
The 15-time All-Star ended up being traded to the Celtics for essentially a group of role players. Whilst with Boston, helped the Celtics win a title. He even led them to a second NBA Finals. To this day, those supporting the team back home in Minneapolis still shake their heads over the decision to trade him.
Utah Jazz — Dominique Wilkins
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This one was rough for the Jazz. Imagine a frontcourt where Karl Malone is running alongside Dominique Wilkins in transition. John Stockton certainly would’ve loved to have had Wilkins available on the wings — just waiting to explode to the rim on back cuts and lobs.
Utah took Wilkins No. 1 overall in 1982. Yet, Wilkins didn’t have a huge interest in playing for the Jazz. Unable to convince him otherwise, he was traded to Atlanta for $1 million and two role players. Suffice it to say, Wilkins became a Hall of Famer after enjoying a ridiculously good career with the Hawks. The two guys Utah got in the deal — Freeman Williams, John Drew — were disasters. Williams played one year for the Jazz (averaging 5.1 PPG). Drew lasted parts of three seasons before eventually being banned from NBA over issues with drug abuse and finances.
Portland Trail Blazers — Moses Malone
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Moses Malone was a dominant big man. He made 13 All-Star appearances and won one title. To this day, he remains as one of the most important members of the 76ers’ franchise. The 3-time league MVP is also often revered as a top-five center in the history of the game. A walking double-double, Malone carved out plenty of space for himself with a wide frame. He then paired that with immense skill in the paint.
The Portland Trail Blazers had Malone’s rights — and actually had the chance to pair him with Maurice Lucas. The two of those guys together would’ve been monstrous. Concerns over team fit led to Portland shipping Malone away before he even played one single game for the franchise. We’ll assume they’d want a mulligan on that deal.
Cleveland Cavaliers — James Worthy
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Let us explain. The Cavs were coming off a dreadful 15-67 season. Cleveland had secured the No. 1 overall pick in the 1982 NBA Draft. However, they had traded that first-round pick two years earlier in a deal which got them a future Lakers’ first rounder along with a player named Don Ford. Ford played parts of three seasons with the Cavs before washing out of the NBA completely by age 29.
The Lakers — on the other hand — took the opportunity to select Worthy with the first pick. He was a cornerstone of the Showtime Era, and developed into one of the NBA’s best hybrid forwards (playing the three and the four). After seven All-Star appearances and three NBA Titles, Worthy is considered royalty within the city of Los Angeles.
