B/R Staff: 5 of the Most Lopsided Draft-Day Trades in Modern NBA History

Due to the time-sensitive nature of its structure and its unpredictability, draft day is one of the most exciting and critical times in the sports calendar. Kevin Costner even made a whole movie about it. 

In the NBA, each team digs deep into the trenches of the war room with seemingly every possible outcome plotted and planned. 

And yet, certain variables—a free-falling prospect, for example—can cause an otherwise level-headed front-office executive to pull the trigger in dramatic fashion.

Who can forget the time Boston Celtics president of basketball operations Danny Ainge unsuccessfully offered four first-round picks for the right to draft Justise Winslow? If the Detroit Pistons or Charlotte Hornets had accepted, where would each franchise be now?

It only takes a moment to strike a deal that can strengthen or deplete the life of an NBA franchise. Many of those historic agreements have come on draft day, and these are some of the most significant ones in the modern NBA era.

The Seattle SuperSonics lost to the Chicago Bulls in the 1996 NBA Finals. While they came up short on the court, the seeds for that defeat were laid almost a decade earlier when they traded back from the No. 5 pick in the 1987 draft, getting No. 8 from the Bulls in order to take Olden Polynice while also picking up a second-rounder (Sylvester Gray) and swapping picks in 1989's first round.

Chicago drafted Scottie Pippen, one of the greatest players of all time and the perfect sidekick to Michael Jordan. Polynice was an average, serviceable center for Seattle. Pippen was named to the Hall of Fame in 2010.

The deal did include those other minor considerations, but none are worth mentioning in the same breath as Pippen, who averaged 15.7 points, 8.2 rebounds, 5.3 assists, 2.3 steals and 1.3 blocks through the six-game Finals against the Sonics.

By 1996, Polynice was long gone from Seattle, traded with multiple first-round picks to the Los Angeles Clippers for Benoit Benjamin, who was eventually dealt with Doug Christie to the Los Angeles Lakers for Sam Perkins. While Perkins was a valuable contributor in Seattle, he was simply not productive in the '96 Finals, shooting just 37.7 percent from the field and 23.5 percent from three-point range.

How different would that series have been if Pippen was on a team with Shawn Kemp and Gary Payton—and if Jordan never had him by his side?

—Eric Pincus

In 1996, the Charlotte Hornets used the No. 13 overall pick on then-17-year-old Kobe Bryant out of Lower Merion High School in Philadelphia, Pennsylvania. 

Bryant would go on to have a Hall of Fame career that included five NBA championships (two Finals MVPs). He became an 18-time All-Star, a 12-time All-Defensive player, the 2007-08 MVP and an Olympic gold medalist, and he sits in fourth place on the all-time scoring leaderboard, trailing only Kareem Abdul-Jabbar, Karl Malone and LeBron James. 

That career didn't come as a member of the Hornets. Charlotte made the now-inexplicable decision to trade the rights to Bryant for just two years of veteran center Vlade Divac. 

"There was such excitement around the pick that Charlotte actually didn't want to go through with the deal," then-Hornets general manager Mitch Kupchak told Rick Bonnell of the Charlotte Observer (h/t CBS Sports' Jasmyn Wimbish). "There was a time there, whether it was Vlade [threatening to retire] or just pressure on the franchise, where the deal was actually in jeopardy."

However, history remembers that then-Lakers general manager Jerry West and Kobe's agent, Arn Tellum, shielded Kobe from a number of workouts to minimize his exposure. The two assumed that if teams didn't have the chance to see Bryant, they'd be dissuaded from using a lottery selection on the 17-year-old. 

Still, Kobe told ESPN's Baxter Holmes in 2015 that he was initially excited to play for Dave Cowens before a conversation with the Hornets head coach changed his mind. 

"Charlotte never wanted me. Cowens told me he didn't want me. It wasn't a question of me even playing here," Bryant said, though Cowens later disputed the story. "They had a couple of guards already, a couple small forwards already. So it wasn't like I would be off the bench much. "

Did this draft-day slight turn Bryant into the Black Mamba, or did Kobe create this narrative just as Michael Jordan created the self-imagined "Nice game, Mike" slight relayed on ESPN's docuseries The Last Dance? Either way, it goes down as one of the worst draft-day trades in NBA history. 

—Preston Ellis

Not only did the Dallas Mavericks acquire one of the greatest players of the 21st century in a draft-day trade, but they also traded down to get him.

Dallas took Michigan Wolverines big man Robert "Tractor" Traylor with the No. 6 overall pick and flipped him to the Milwaukee Bucks for the rights to their two picks in the 1998 draft. One was Notre Dame forward Pat Garrity; the other was an intriguing German power forward named Dirk Nowitzki.

Traylor played just two seasons for the Bucks, averaging 4.5 points and 3.2 rebounds in 13.3 minutes per game before he was traded to the Cleveland Cavaliers in June 2000.

Nowitzki had been a star in Germany, but there was reason to be skeptical of his NBA impact. He had passed up multiple American college offers, choosing instead to jump straight to the NBA, which turned some teams off. Throughout the NBA, international scouting was nowhere near as robust as it is today, so teams were unsure how his unconventional skill set as a seven-foot three-point shooter would translate to the NBA. 

His career ultimately turned out OK.

—Sean Highkin

Trading for one of Gregg Popovich's favorite players seems smart, but the fact that the San Antonio Spurs would let go of this favorite in the first place should've tingled the Indiana Pacers' spidey senses. San Antonio saw something special in 2011's 15th pick, Kawhi Leonard.

Soon, the entire hoops world saw it, too.

It took Leonard just three seasons after being traded for George Hill, as well as the rights to Davis Bertans (the 42nd pick) and Erazem Lorbek, to make his first All-Defensive appearance, and he capped that campaign with a Finals MVP.

Leonard started booking annual All-Star trips shortly thereafter, snagged back-to-back Defensive Player of the Year awards in 2014-15 and 2015-16 and added another Finals MVP last summer.

The 28-year-old can make a legitimate argument as the best player on the planet. He ranks fourth in ESPN's real plus-minus and fifth in player efficiency rating. If he's not the most powerful two-way force in basketball, he's within claw's reach of whoever is.

Hill is...fine. In fact, PER paints him as almost perfectly average (career 15.1; league average is 15.0). He had a mostly solid five-year stretch in the Circle City, but he was never mistaken for a star.

There's a non-zero chance Leonard ends his career with a spot on basketball's Mt. Rushmore. Tears should still be flowing in Indiana over this disastrous deal.

—Zach Buckley

While it seemed like a fair deal at the time, the Kevin Love-O.J. Mayo trade between the Minnesota Timberwolves and Memphis Grizzlies has turned out to be extremely one-sided.

In 2008, the Grizzlies sent the No. 5 overall pick (Love) along with Mike Miller, Brian Cardinal and Jason Collins to the Wolves for the No. 3 pick (Mayo), Antoine Walker, Marko Jaric and Greg Buckner.

Love and Mayo were both superstar prospects, one a bruising power forward and the other a dynamic shooting guard. While both enjoyed successful rookie seasons, their career trajectories would then take very different paths. 

Love went on to become one of the best players in Minnesota history, averaging 19.2 points, 12.2 rebounds and 2.5 assists during his six seasons with the franchise. He completely transformed his body, cutting weight while establishing a reliable outside shot. He made just two three-pointers during his rookie season before increasing his total to 190 by Year 6.

His trade to the Cleveland Cavaliers in 2014 helped the Cavs reach four straight NBA Finals and win the 2016 title.

Mayo's scoring average of 18.5 points per game during his rookie season would end up being a career high as his production, diet and work ethic slowly slipped away.

Lasting just four seasons with the Grizzlies, he bounced around from the Dallas Mavericks to the Milwaukee Bucks before he was suspended from the NBA in 2016 for violating the league's anti-drug policy, later admitting to using marijuana and abusing prescription pain medication.

—Greg Swartz