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Lessons From the 14 Biggest NBA Deadline Trades

Posted by Jonah Gardner on February 18, 2016

The 2016 NBA Trade Deadline has, is, or will be passing as you read this. The long term consequences will shake out over the next few months and even years, but we can look back at past deadlines to determine just how important deadline deals tend to be.

Last year's Trade Deadline shows that it takes a few years to be able to truly evaluate the impact of a trade. At the time, the best deal of the day seemed to be the Goran Dragic Trade. Miami picked up Dragic, the reigning MIP who had been worth nearly 23 NBA Win Shares in his career with Phoenix up to that point, for two 1st rounders and mostly filler players.

Since the trade, Goran Dragic has contributed 5 WS to Miami, but he's also signed a big new contract. His scoring and his efficiency have plummeted this season and, as Miami's roster ages, those two draft picks are starting to look more valuable.

Compare that to another trade involving a Phoenix Suns PG. In a 3-teamer, the Celtics acquired Isaiah Thomas and Jonas Jerebko for a Cavaliers' 1st rounder and not much else. Most agreed at the time that Dragic was the more valuable player, but Thomas has outperformed him. Since the trade, Thomas has been worth 9 WS and his scoring has leapt up 6 PPG. Even Jerebko has been worth 3 WS, not much less than what Miami has received from Dragic.

So let's take a look back at some of the biggest NBA trade deadline deals, using the benefit of hindsight to see who really gained the most from making them. It's not necessarily fair to say one team or the other "won", since, as you'll see, a lot of these trades rely on things that the front offices making them couldn't have possibly known at the time. But, perhaps, there are lessons here that GMs can take into future dealings.

A couple of notes before we start. I'm using a generous definition of the Trade Deadline to include any trade that happened in mid-January, February, or March, because it's my column and I can do what I want. To quantify value, I'm using Win Shares, a metric that Basketball Reference adapted from the baseball stat devised by Bill James. WS is a stat that awards portions of every team win to every player on the team, based on how much they contributed (positively or negatively) to said win.

The biggest trades, as defined on this list, are the ones with 100 or more Win Shares in past or future value. In other words, every trade on this list is one where all the players involved had contributed 100 WS to the teams trading them or where they would go on to contribute 100 WS to the teams that acquired them. These are trades where franchise players moved on, where teams acquired a new franchise player, or where both happened.

For each trade, we'll show the past WS of all the players in the trade for the team that traded them (so, for example, the number for Rasheed Wallace doesn't include his WS in Portland) and the future WS the player would accumulate for the team that traded for them (so, for example, Seattle's WS in the Ray Allen trade won't reflect his time in Boston). I've also included, in parentheses, the percentage of past WS each team sent and the percentage of future WS each team acquired. You can think of that as a rough measure of who "won" the trade.

Got it? Then let's get started.

Lesson 1: Selling a legend is tricky

Los Angeles Clippers Receive: Dominique Wilkins, 1994 1st Round Pick (Greg Minor). 31 Past WS sent (22.4%), 2.6 Future WS received (66.7%)

Atlanta Hawks Receive: Danny Manning.  107.4 Past WS sent (77.6%), 1.3 Future WS received (33.3%)

Houston Rockets Receive: Clyde Drexler and Tracy Murray54.5 Past WS sent (32.8%), 26.9 Future WS received (89.4%)

Portland Trail Blazers Receive: Otis Thorpe, Marcelo Nicola, 1995 1st Round Pick (Randolph Childress). 111.9 Past WS sent (67.2%), 3.2 Future WS received (10.6%)

Dominique Wilkins was in his 12th year with the Atlanta Hawks when the franchise decided they'd rather trade him than give him a massive new contract. Unfortunately, because of that impending new contract, and Wilkins' age, the Hawks couldn't get back more than a Win Share. This trade makes the list because of Wilkins' lengthy tenure, but in terms of return, it left much to be desired.

Still, given that Wilkins's career was nearly over, the Hawks got a better share of the overall WS pie than the Trail Blazers did, when they traded Clyde Drexler. Drexler is still the Blazers' all-time Win Shares leader and in return they got Thorpe, who would be gone months later, Nicola, who never came to the US, and a pick that would go to a player who logged 375 total minutes for Portland. At least Clyde got a ring, though!

Lesson 2: But if you get it right, it's worth it

Milwaukee Bucks Receive: Desmond Mason, Gary Payton56.1 Past WS sent (29.6%), 16.3 Future WS received (22.9%)

Seattle Supersonics Receive: Ray Allen, Ronald Murray, Kevin Ollie, 2003 1st Round Pick (Luke Ridnour). 133.4 Past WS sent (70.4%), 54.9 Future WS received (77.1%)

Gary Payton was having an All-Star year when Seattle, apparently concerned about re-signing him, shipped him to Milwaukee. In exchange, they got the best shooter of his generation. Ray Allen would go on to chip in 38.2 WS as a Sonic before being sent to Boston, while GP would leave for LA in free agency, contributing just 2.9 WS to the Bucks.

Lesson 3: Good drafting can make a trade

Atlanta Hawks Receive: Tom Henderson, 1977 1st Round Pick (Greg Ballard). 6.6 Past WS sent (39.5%), 62.9 Future WS received (51.7%)

Washington Bullets Receive: Truck Robinson, 1977 1st Round Pick (Tree Rollins). 10.1 Past WS sent (60.5%), 58.8 Future WS received (48.3%)

Milwaukee Bucks Receive: Sam Cassell, Chris Gatling, Paul Grant10.7 Past WS sent (27.8%), 36.7 Future WS received (30.4%)

New Jersey Nets Receive: Elliot Perry, Chris Carr, Stephon Marbury, Bill Curley13.9 Past WS sent (36.0%), 20.0 Future WS received (16.6%)

Minnesota Timberwolves Receive: Terrell Brandon, Brian Evans, 1999 1st Round Pick (Wally Szczerbiak). 14.0 Past WS sent (36.2%), 64.0 Future WS received (53.0%)

Detroit Pistons Receive: Rasheed Wallace, Mike James41.7 Past WS sent (91.9%), 38.7 Future WS received (37.7%)

Atlanta Hawks Receive: Chris Mills, Zeljko Rebraca, Bob Sura, 2004 1st Round Pick (Josh Smith). -0.1 Past WS sent (-0.3%), 50.2 Future WS received (48.9%)

Boston Celtics Receive: Chucky Atkins, Lindsey Hunter, 2004 1st Round Pick (Tony Allen). 3.8 Past WS sent (8.4%), 13.8 Future WS received (13.4%)

If you ask any fan who remembers the 2004 Trade Deadline who the biggest acquisition that year was, they'd say Sheed and Sheed a 2nd time. And, from a historic perspective, they'd be right, since Wallace helped the Detroit Pistons win a title. However, the player who had the biggest on-court impact for the team that traded for him in 2004 wasn't even in the NBA at the time.

Although the players who travelled to Atlanta in the Sheed trade didn't amount to much, they did make the most of the draft pick they got. While Josh Smith has fallen on tough times, he contributed 47.6 WS to the Hawks, more than the 37.3 Sheed racked up as a Piston. Thanks to the pick, and their smart use of it, the Hawks actually won the largest percentage of future WS in the Rasheed Wallace trade (of course, it doesn't look quite as good if you factor in the 14 WS they gave up to acquire Wallace for one game).

None of the trades in this section would have made the list based on the players who were actually in the trade. Instead, smart drafting helped some of these teams turn average-seeming trades into big wins.

4. You can't really predict how a trade will impact you

Washington Wizards Receive: Drew Gooden, Josh Howard, Quinton Ross and James Singleton67.4 Past WS sent (60.7%), 4.6 Future WS received (27.4%)

Dallas Mavericks Receive: Caron Butler, Brendan Haywood and DeShawn Stevenson43.6 Past WS sent (39.3%), 12.2 Future WS received (72.6%)

On paper, this move seemed to bring Dallas the missing piece they needed to win a championship: Caron Butler. Yet, one year after this trade, when the Mavericks made their Finals run, Butler was in a suit, injured and unable to play. On paper, DeShawn Stevenson was a throw-in. Yet, in the 2011 NBA Finals, it was Stevenson whose 3s and D helped lead to the Mavs' upset victory over the Miami Heat. The Mavericks wouldn't have won the Finals without this trade, just not for the reason they were expecting when they made it.

5. The Rudy Gay Trade was weird

Toronto Raptors Receive: Rudy Gay, Hamed Haddadi. 56.1 Past WS sent (39.0%), 1.9 Future WS received (12.9%)

Memphis Grizzlies Receive: Austin Daye, Tayshaun Prince, Ed Davis, 2013 2nd Round Pick (Jamaal Franklin). 30.8 Past WS sent (21.4%), 9.8 Future WS received (66.7%) 

Detroit Pistons Receive: Jose Calderon60.3 Past WS sent (42.0%), 3 Future WS received (20.4%)

This trade makes our list because it involved 3 players who amassed over 25 WS for their respective franchises changing teams. However, it serves as a warning that, in the NBA, your past accomplishments can fade very quickly. Prince and Calderon, who accounted for over 98 of the past Win Shares in this trade, were basically just salary figures used to match the money on Rudy Gay's monster contract.

The Grizzlies "win" this trade, by virtue of the fact that Prince stayed in town till 2014 and averaged 27 MPG for a playoff team and by virtue of the fact that Rudy Gay would spend less than a year in The True North. However, it's tough to argue anyone here really won.

6. It's very, very tough to get good value back for a superstar

Philadelphia 76ers Receive: Wilt Chamberlain26.3 Past WS sent (19.0%), 71.2 Future WS received (84.6%)

San Francisco Warriors Receive: Connie Dierking, Paul Neumann, Lee Shaffer, cash. 112.4 Past WS sent (81.0%), 13 Future WS received (15.4%)

Honestly, the most amazing part of this trade may be that Wilt accumulated 71.2 WS in just 3 and a half years as a 76er. Things had gotten bad for Wilt in San Francisco, but that's a tough return for one of the greatest to ever play the game

7. But it's not impossible

Los Angeles Lakers Receive: Pau Gasol, 2010 2nd Round Pick (Devin Ebanks). 6.2 Past WS sent (10.3%), 59.7 Future WS received (48.7%)

Memphis Grizzlies Receive: Kwame Brown, Javaris Crittenton, Marc Gasol, Aaron McKie, 2008 1st Round Pick (Donte Greene), 2010 1st Round Pick (Greivis Vasquez). 53.8 Past WS sent (89.7%), 62.8 Future WS received (51.3%)

New York Knicks Receive: Carmelo Anthony, Chauncey Billups, Anthony Carter, Renaldo Balkman, Shelden Williams, Corey Brewer34.8 Past WS sent (27.1%), 40.2 Future WS received (42.9%)

Denver Nuggets Receive: Wilson Chandler, Raymond Felton, Danilo Gallinari, Timofey Mozgov, Kosta Koufos cash, 2012 2nd Round Pick (Quincy Miller), 2013 2nd Round Pick (Romero Osby) and a 2014 1st Round Pick (traded). 91.5 Past WS sent (71.4%), 51.8 Future WS received (55.3%)

Minnesota Timberwolves Receive: Anthony Randolph, Eddy Curry1.9 Past WS sent (1.5%), 1.7 Future WS received (1.8%)

The Pau Gasol trade, at the time, seemed like one of the biggest steals in NBA history. Now, almost a decade later, by percentage of future Win Shares, Memphis actually won the trade. Lakers fans probably won't complain too much about a trade that convinced Kobe to stay and got them 2 rings, but Pau's 59.2 WS as a Laker are a little behind Marc's 62.2 in Memphis. In fact, the younger Gasol has been worth more WS as Grizzly than the older one was, making this the rare trade where a team dealt a superstar and improved their long-term situation.

The jury is actually still out on the Melo Trade, since Anthony, Gallinari, and Chandler remain on the teams that acquired them, but, at this point, Denver has an over-10 WS lead. At the time, the conventional wisdom was that the Knicks may have given up too much for a player they'd be able to sign as a free agent over the summer. Unlike the Gasol trade, the Win Shares seem to bear that out in this case.

8. Being a Cavs fan sucks 

Phoenix Suns Receive: Tyrone Corbin, Kevin Johnson, Mark West, 1988 1st Round Pick (Dan Majerle), 1988 2nd Round Pick (Dean Garrett), and a 1989 2nd Round Pick (Greg Grant). 62.1 Past WS sent (85.2%), 179.8 Future WS received (73.7%)

Cleveland Cavaliers Receive: Larry Nance, Mike Sanders, 1988 1st Round Pick (Randolph Keys). 10.8 Past WS sent (14.8%), 64.3 Future WS received (26.3%)

Detroit Pistons Receive: Kenny Carr and Bill Laimbeer. 10 Past WS sent (34.4%), 99 Future WS received (74.9%)

Cleveland Cavaliers Receive: Phil Hubbard, Paul Mokeski, 1982 1st Round Pick (John Bagley), 1982 2nd Round Pick (Dave Magley). 19.1 Past WS Sent (65.6%), 33.2 Future WS Received (25.1%)

Cleveland Cavaliers Receive: Antawn Jamison, Sebastian Telfair63.4 Past WS sent (58.3%), 7.8 Future WS received (67.8%)

Washington Wizards Receive: Zydrunas Ilgauskas, Emir Preldzic, Al Thornton, 2010 1st Round Pick (Lazar Hayward). 41.4 Past WS sent (38.1%), 2 Future WS received (17.4%)

Los Angeles Clippers Receive: Drew Gooden. 4 Past WS sent (3.7%), 1.7 Future WS received (14.8%)

There are three trades on this list that involve the Cavs. Two of them are trades that the Cavs soundly lost, including the Kevin Johnson trade, where Cleveland gave up the largest total future value of any trade on this list. You know a trade is bad, when it cost you more Win Shares than trading away Wilt Chamberlain.

Then there's the Jamison trade, a win for the Cavs, but one that only calls to mind 2010-2012, a period where Cleveland lost in a 2nd-round shocker, watched LeBron James announce he was leaving on live TV, and spent the next 2 years as one of the worst teams in the league.

Is there a trade you think is missing from the list? Or are you just interested in reading more about past trade deadlines? Either way, make sure to check out the Trade Tool at, where you can explore every trade in NBA history.

2 Responses to “Lessons From the 14 Biggest NBA Deadline Trades”

  1. Robert P. Says:

    This is a really cool post! On the topic of trades -- I'm fascinated by all the movement that happened around the time of the NBA-ABA merger. For example, one trade that fascinates me is the Buffalo Braves decision to move Moses Malone in 1976. At the start of the season, the Braves had a roster with Moses Malone (age 21), Adrian Dantley (20), Bob McAdoo (25) and Randy Smith (28). It's crazy to think what would've happened if they had been able to keep them together. So much happened in those first few seasons of the merger.

  2. Jonah Gardner Says:

    Wow, what a team that would have been! Definitely a fascinating hypothetical