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NBA PM: Largest Second-Round Contracts

A look at the second-round picks who signed the biggest contracts in recent years.

Cody Taylor



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.


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.

Cody Taylor is an NBA writer in his fourth season with Basketball Insiders, covering the NBA and NCAA out of Orlando and Miami.


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Middleton, Bucks Aiming To ‘Lock In’ As Season Comes To Close

Spencer Davies catches up with Milwaukee Bucks swingman Khris Middleton in a Basketball Insiders exclusive.

Spencer Davies



Basketball Insiders had the chance to chat with Khris Middleton about the direction of the Milwaukee Bucks as the season comes to a close.

You guys won three out of four before you came into Cleveland. What was working during that stretch?

Just being us. Doing it with our defense, playing fast-paced offense. Just trying to keep teams off the three-point line. We haven’t done that. We didn’t do that [Monday] or two games ago, but it’s something we’ve just gotta get back to.

With the offense—it seems like it’s inconsistent. What do you think that’s got to do with mostly?

Just trying to do it by ourselves sometimes. Standing, keeping the ball on one side of the floor. We’re a better team when we play in a fast pace. And then also in the half court, when we move the ball from side-to-side it just opens the paint for everybody and there’s a lot more space.

For you, on both ends you’ve been ultra-aggressive here in the last couple weeks or so, does that have to do with you feeling better or is it just a mindset?

I’ve been healthy all year. Right now, it’s the end of the season. Gotta make a push. Everybody’s gotta lock in. Have to be confident, have to be aggressive. Have to do my job and that’s to shoot the ball well and to defend.

Have you changed anything with your jumper? Looking at the past couple months back-to-back, your perimeter shooting was below 32 percent. In March it’s above 45 percent.

I feel like I got a lot of great looks earlier this year. They just weren’t falling. Right now, they’re falling for me, so I have the same mindset that I had when I was missing and that’s to keep on shooting. At some point, they’re gonna go down for me.

Is knowing that every game at this point means more an extra motivator for you guys?

Definitely. We’re basically in the playoffs right now. We’re in a playoff series right now where we have to win games, we have to close out games, in order to get the seeding and to stay in the playoffs. Each game and each possession means something to us right now.

Is it disappointing to be in the position the team is in right now, or are you looking at it as, ‘If we get there, we’re going to be alright’?

I mean, we wish we were in a better position. But where we’re at right now, we’re fine with it. We want to make that last push to get higher in the seeding.

Lots of changes have gone on here. Eric Bledsoe came in two weeks into the season. You had the coaching change and lineup changes. Jabari Parker’s been getting situated before the postseason. How difficult does that make it for you guys to build consistency?

Yeah, it was tough at first. But I think early on we had to adjust on the fly. We didn’t have too many practices. There was a stretch where we were able to get in the film room, get on the court, and practice with each other more.

Now it’s just at a point where we’re adding a lot of new guys off the bench where we have to do the same things—learn on the fly, watch film. We’re not on the court as much now, but we just have to do a great job of buying in to our system, try to get to know each other.

Does this team feel like it has unfinished business based on what happened last year?

Definitely. Last year, we felt like we let one go. Toronto’s a great team. They’re having a hell of a season this year, but I feel like we let one go. This year’s a new year—a little add of extra motivation. We’ve been in the playoff position before, so hopefully, we learn from it when we go into it this year.

Would you welcome that rematch?

I mean, we welcome anybody man. We showed that we compete with any team out here. We can’t worry about other teams as much. We just have to be focused on us.

What has to happen for you guys to achieve your full potential?

Lock in. Just play as hard as we can, play unselfish, and do our job out there night-in, night-out.

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NBA Daily: Raptors Look To Fine-Tune The Defense

The Toronto Raptors’ defense had a letdown against the Cavaliers, but has been outstanding overall.

Buddy Grizzard



The Cleveland Cavaliers and Toronto Raptors engaged in an offensive shootout on Wednesday that could be a playoff preview. The Cavs protected home court with a single-possession, 132-129 victory. Afterward, the Raptors spoke about the types of defensive adjustments the team needs to make as the postseason rapidly approaches.

“That’s how a playoff game would be,” said DeMar DeRozan, who missed a three at the buzzer that could have forced overtime. “This is a team we’ve been playing against the last two years in the postseason. Understanding how we can tighten up things defensively, how to make things tougher for them [is key].

“[It’s] little small things that go a long way, and not just with them … with every team.”

Raptors coach Dwane Casey concurred with DeRozan that fine-tuning of the defense is needed. He also pointed out that, with young contributors such as center Jakob Poeltl and power forward Pascal Siakam on the roster, defensive experience against the league’s best player, LeBron James, is something they will have to gain on the fly.

“I don’t think Jakob Poeltl played against him that much, and Siakam,” said Casey. “This is their first time seeing it. I thought Jak and Pascal did an excellent job, but there are certain situations where they’ve got to read and understand what the other team is trying to do to them.”

Poeltl was outstanding, leading the bench with 17 points and tying for the team lead in rebounds with eight. Casey praised the diversity of his contributions.

“I thought he did an excellent job of rolling, finishing, finding people,” said Casey. “I thought defensively, he did a good job of protecting the paint, going vertical. So I liked what he was giving us, especially his defense against Kevin Love.”

Basketball Insiders previously noted how the Raptors have performed vastly better as a team this season when starting point guard Kyle Lowry is out of the game. Much of that is due to Fred VanVleet’s emergence as one of the NBA’s best reserve point guards. VanVleet scored 16 points with five assists and no turnovers against Cleveland. It’s also a reflection of how good Toronto’s perimeter defense has been up and down the roster.

According to ESPN’s defensive Real Plus-Minus statistic, three of the NBA’s top 15 defensive point guards play for the Raptors. VanVleet ranks seventh while Lowry is 12th and Delon Wright is 14th. Starting small forward OG Anunoby ranks 16th at his position.

The Raptors also rank in the top five in offensive efficiency (third) and defensive efficiency (fifth). Having established an identity as a defensive team, especially on the perimeter, it’s perhaps understandable that Lowry was the one player in the visiting locker room who took the sub-standard defensive showing personally.

“It was a disgraceful display of defense by us and we’ve got to be better than that,” said Lowry. “We’ve got to be more physical. They picked us apart and made a lot of threes. We’ve got to find a way to be a better defensive team.”

Lowry continued the theme of fine-tuning as the regular season winds down.

“I think we’ve just got to make adjustments on the fly as a team,” said Lowry. “We can score with the best of them, but they outscored us tonight. We got what we wanted offensively. We’re one of the top teams in scoring in the league, but we’re also a good defensive team.”

Lowry was clearly bothered by Toronto’s defensive showing, but Casey downplayed the importance of a single regular-season game.

“We’ve got to take these games and learn from them, and again learn from the situations where we have to be disciplined,” said Casey. “It’s not a huge thing. It’s situations where we are that we’ve got to learn from and be disciplined and not maybe take this step and over-help here. Because a team like that and a passer like James will make you pay.”

While the Raptors continue to gain experience and dial in the fine defensive details, Casey was insistent that his players should not hang their heads over falling short against Cleveland.

“Hopefully our guys understand that we’re right there,” said Casey.

The Raptors host the Brooklyn Nets tonight to open a three-game home stand that includes visits from the Clippers Sunday and the Nuggets Tuesday. After that, Toronto visits the Celtics March 31 followed by a return to Cleveland April 3 and a home game against Boston the next night. With three games in a row against the other two top-three teams in the East, the schedule presents plenty of opportunities for the Raptors to add defensive polish before the playoffs begin.

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NBA Daily: Jaylen Brown Set To Return For Celtics

The Celtics finally got some good news on Thursday. Jaylen Brown’s return is imminent.

Moke Hamilton



Finally, some good news for the Boston Celtics.

Jaylen Brown is set to return to action.

Brown has been M.I.A. since sustaining a concussion during the team’s 117-109 victory over the Minnesota Timberwolves back on March 8, but has traveled with the team to Portland and is expecting to return to the lineup on Sunday when the Celtics do battle with the Sacramento Kings.

As the Celts gear up for a playoff run, which they hope will result in them ending LeBron James’ reign atop the Eastern Conference, they’ve picked the wrong time to run into injury issues. Along with Brown, both Kyrie Irving and Marcus Smart have each been conspicuous by their absences, and the team could certainly use all of their pieces as they attempt to enter the postseason on a high note.

Fortunately for Boston, with the Toronto Raptors leading them by 4.5 games in the standings and the Celts ahead of the Cleveland Cavaliers by a comfortable six games, Brad Stevens’ team is enjoying the rare situation of having a playoff seed that appears to be somewhat locked in.

Still, with the team only able to go as far as its young rotation will carry it, Brown addressed the media on Thursday.

“I’m feeling a lot better. I’m just trying to hurry up and get back,” Brown said, as quoted by

“I’m tired of not playing.”

Stevens is probably tired of him not playing, too.

As we head into the month of April, playoff-bound teams and conference contenders begin to think about playing into June, while the cellar-dwellers and pretenders begin to look toward the draft lottery and free agency.

What’s funny is that in the midst of the Raptors and their rise out East, the Celtics and their dominance has become a bit of a forgotten storyline. When Gordon Hayward went down on opening night, the neophytes from the Northeast were thought to be a decent team in the making whose ceiling probably wasn’t anywhere near that of the Cavs, the Raptors and perhaps even the Washington Wizards.

Yet through it all, with the impressive growth of Jaylen Brown, impressive rookie Jayson Tatum and the rise of Irving as a franchise’s lynchpin, the Celtics stormed out the games to the tune of a a 17-3 record. What made the strong start even more impressive was the fact that the team won 16 straight games after beginning the season 0-2.

Although they weren’t able to keep up that pace, they began the month of February having gone 37-15 and turned a great many into believers. With their spry legs, team-first playing style and capable leader in Irving, the Celtics, it was thought, were a true contender in the Eastern Conference — if not the favorite.

Since then, and after experiencing injuries to some of its key cogs, the team has gone just 11-8.

In the interim, it seems that many have forgotten about the team that tantalized the Eastern Conference in the early goings of the season.

Brown’s return, in one important respect, will signify a return to Boston’s prior self.

With Marcus Smart having recently undergone surgery to repair a torn tendon in his right thumb, he is expected to be out another five weeks or so, meaning that he’ll likely miss the beginning of the postseason.

As for Irving, although reports say that his ailing knee has no structural damage, everything the Celtics hope to accomplish begins and ends with him. FOX Sports 1’s Chris Broussard believes that it’s no slam dunk that Irving returns to action this season, but he’s in the minority. This team has simply come too far to not give themselves every opportunity to compete at the highest level, so long as doing so doesn’t jeopardize the long term health of any of the franchise’s cornerstones.

Make no mistake about it, the Celtics are far from a finished product. With their nucleus intact and flexibility preserved, they will have another offseason with which to tinker with their rotation pieces and plug away at building a champion.

But here and now, with what they’ve got, the Celtics are much closer than any of us thought they would be at this point.

And on Sunday, when Jaylen Brown rejoins his team in the lineup, to the delight of the Boston faithful, the Celtics will be that much closer.

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