NBA PM: Largest Second-Round Contracts

It’s been widely covered to this point that NBA teams will have a lot of money to spend this summer. With the salary cap rising to an estimated $92 million next season, players will be signing some of the largest contracts the league has seen to date.

Some of the league’s top players, like LeBron James, Kevin Durant, Al Horford, DeMar DeRozan and Hassan Whiteside, can become unrestricted free agents this offseason. The most notable thing about that group of players is Whiteside was the only one drafted outside of the first round.

Whiteside’s story is well-known to this point. He was drafted with the 33rd overall pick by the Sacramento Kings in the second round of the 2010 draft. He bounced around between the D-League and overseas, but now stands to get a significant pay raise this summer as he’s projected to earn a max-contract in free agency.

It’s important to note that most of the league’s top players were drafted in the first round. There have been some cases in which players have gone on to have successful careers after being drafted in the second round, but we’ve also seen many second-rounders eventually fall out of the league after just a few seasons. Without the guaranteed contract that first-rounders get, it’s tougher to stick in the league.

With Whiteside expected to sign a massive contract this summer, we began wondering which second-round draft picks have signed the biggest deals. For this list, we found the richest contracts signed after the 2000 draft.

8. Khris Middleton: 39th pick, Detroit Pistons – 2012

Middleton spent just one season with Detroit before being traded to Milwaukee. His playing time immediately increased during his first season with the Bucks, and he increased his points per game from 6.1 to 12.1. He averaged 13.4 points, 4.4 rebounds and 2.3 assists per game the following season, which allowed him to sign a five-year deal worth $70 million last summer. Re-signing Middleton was one of the first moves the Bucks made once free agency began last July, which goes to show how important he was to the team. He averaged a career-high 18.2 points, 4.2 assists and 3.8 rebounds this season.

7. Carlos Boozer: 35th pick, Cleveland Cavaliers – 2002

Boozer has turned in arguably one of the most productive careers for a former second-round pick. He’s spent 13 years in the league and holds career averages of 16.2 points and 6.8 rebounds per game. The best stretch of his career happened during the six years he played for the Utah Jazz, where he averaged 19.3 points, 10.5 rebounds and three assists per game. That strong play in Utah gave Boozer the opportunity to sign a five-year, $75 million deal with the Chicago Bulls in 2010. Boozer was a crucial part of the Bulls’ playoff runs under Tom Thibodeau.

6. Draymond Green: 35th pick, Golden State Warriors – 2012

It seems hard to believe that Green was drafted in the second round in 2012 considering that he is one of the best players in the league today. In his case, the talent was always there, it was just a matter of finding playing time and the right role. An injury to David Lee at the beginning of last season opened the door for Green, and the rest is history.

Green used his draft position as fuel in his rise to become one of the league’s best players. Recently, Green was asked about that 2012 draft, and he proved that it’s still something he thinks about as he named every player that was drafted ahead of him.

“First was Anthony Davis to New Orleans,” he says. “Then Charlotte took (Michael) Kidd-Gilchrist. Then Washington took Bradley Beal. Fourth was Cleveland: Dion Waiters. … “Eight was Toronto: Terrence Ross. … “Sixteen was Houston: Royce White …”

Green averaged 11.7 points, 8.2 rebounds and 3.7 assists per game last season. He started all 79 games he played in and then signed a five-year, $82 million deal with the Warriors last summer. He now finds himself as the glue that holds the Warriors together and one of the most valuable players on the team.

5. DeAndre Jordan: 35th pick, Los Angeles Clippers – 2008

We’re all familiar with Jordan’s free agency fiasco last offseason. He was very close to signing with the Dallas Mavericks, but would eventually return to the Clippers on a four-year contract worth $87.6 million. Jordan’s career really took off when head coach Doc Rivers joined the Clippers in 2013. He averaged 8.8 points, 7.2 rebounds and 1.2 blocks per game during the season before Rivers became the head coach, then increased his numbers to 10.4 points, 13.6 rebounds and 2.5 blocks per game during Rivers’ first season on the job. He’s now regarded as one of the best centers in the league.

4. Michael Redd: 43rd pick, Milwaukee Bucks – 2000

Redd proved to be a prolific scorer during his 12 years in the NBA. He had a run in which he scored at least 21 points per game in six-straight seasons from 2003 to 2009. Redd signed a six-year deal with the Bucks during that run, which was worth $90 million. Unfortunately, Redd suffered two separate ACL and MCL tears in the same knee, which ended his career earlier than expected. Redd still holds the Bucks’ single game scoring record with 57 points.

3. Goran Dragic: 45th pick, San Antonio Spurs – 2008

Dragic played sparingly during his first few seasons in the league. He worked his way into being a starting point guard during his second stint with the Phoenix Suns, and would eventually become the NBA’s Most Improved Player in 2014 after averaging 20.3 points and 5.9 assists per game. The Suns traded him to the Miami HEAT at last season’s trade deadline, and Dragic would eventually re-sign on a five-year deal worth $90 million.

2. Marc Gasol: 48th pick, Los Angeles Lakers – 2007

Gasol has established himself as one of the best centers in the game. When it’s all said and done, he could end up being the Memphis Grizzlies’ best player of all-time. He signed a four-year, $57 million deal back in 2011, but it was clear that he was outplaying that deal by the time it ended. He was one of the top free agents on the market last summer, but ultimately wanted to remain in Memphis and he signed a five-year, $110 million max-deal.

1. Gilbert Arenas: 31st pick, Golden State Warriors – 2001

Arenas is one of the most decorated players on this list. He was a five-time All-Star with the Washington Wizards, and was also named to the All-NBA Second Team in 2007 and the All-NBA Third Team during the two seasons prior. Arenas turned in his best season in the league in 2005-06 when he averaged 29.3 points and 6.1 assists per game. Agent Zero would go on to sign a six-year, $111 million contract with the Wizards in 2008.

Arenas said at the time that he agreed to take about $16 million off of the final number in order to give the Wizards some cap flexibility. Knee problems and off-court issues caused Arenas to appear in just 134 games after signing that deal. Arenas would eventually be traded to the Orlando Magic in 2010, and the Magic would later use the amnesty provision to waive Arenas in 2011. Despite not playing in 2014, Arenas was still ranked as the 30th highest-paid athlete in the world.

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We’ve seen a number of second-rounders prove to have long and successful careers, despite flying under the radar during their respective draft class. Hassan Whiteside will become the latest example of that this summer once he signs his new contract.

In addition to Whiteside, Chandler Parsons also stands in line to sign a big deal this summer as well. Parsons was taken by the Houston Rockets in the second round of the 2011 draft.