Desperate times: Behind the madcap craze of massive NBA draft picks packages

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Who were the Minnesota Timberwolves competing against when they traded three playoff rotational players and the rights to seven of their first-round draft picks from this decade for 30-year-old center Rudy Gobert?

If you are the head of basketball operations on the other end of the phone, all it takes is one new ownership group or empowered executive desperate to make a splash, or both, to outbid a player's value. A reckless negotiation should never set a market, but the 2019 trade of Anthony Davis to the Los Angeles Lakers, who also were not seriously negotiating against anyone, promoted a trend of unprotected pick-heavy packages.

The Brooklyn Nets, who are canvassing the market in the aftermath of Kevin Durant's trade request, are learning the hard way that there are only so many imprudent front offices. The Nets can and have asked for Scottie Barnes as the headliner of a deal that includes even more draft equity than the Timberwolves spent. That doesn't mean Toronto Raptors president of basketball operations Masai Ujiri has to meet their request.

General managers have the option to say, "No."

Ujiri knows. He waited out the market to obtain Kawhi Leonard in 2018. The San Antonio Spurs sought pick-centric packages for him four years ago, but the Los Angeles Lakers and Philadelphia 76ers were among the suitors who refused to mortgage their future for a superstar with one year remaining on his contract, so the Raptors kept their offer to DeMar DeRozan, Jakob Poeltl and a protected first-round pick.

Any price might have been worth the cost — considering Toronto won the title — and that is the argument you will hear in L.A., where the latest championship banner was unfurled before a bleak future. The Raptors may not have beaten the healthy Golden State Warriors in 2019, or the Lakers may not have won without a four-month layoff in 2020, but they did, so there is no second-guessing the moves. They won their coin tosses.

That is what all these draft pick hauls are — at their best, a coin flip.

Long live The Nets Picks

At their worst, they feel like a two-headed coin. Three unprotected first-round picks and a pick swap felt like an overpay from the moment the Nets dealt them to the Boston Celtics for an aging Kevin Garnett and Paul Pierce in 2013. That the Celtics turned those picks into Jayson Tatum, Jaylen Brown and four Eastern Conference finals appearances in the decade since makes it look worse. Danny Ainge won his coin tosses.

The former Celtics executive turned Utah Jazz decision-maker was also on the other side of the Gobert deal, and he will hope to flip his picks into All-Stars again. He could just as easily be left empty-handed.

Talent evaluation helps, but we saw the Sixers choose Markelle Fultz and Ben Simmons over Tatum and Brown. That alternate universe does not excuse the Garnett and Pierce trade, but it softens the losses.

If pick-laden trades truly were a 50-50 proposition, the Nets are due for another win. As ESPN's Zach Lowe recently detailed, the six trades sending three or more future first-round picks to one team since 2019 equal the number of similar deals in 43 years prior. Brooklyn has been involved in three of those already; Durant could make it four. The first of them came in 2004, when the Denver Nuggets paid three first-round picks in a sign-and-trade for Kenyon Martin. The Nets turned two of those picks into Vince Carter five months later.

Brooklyn's recent trade of three first-round picks and four swaps for James Harden has yet to bear fruit for the Houston Rockets, but it hasn't much helped the Nets, either. Brooklyn still has Simmons, Seth Curry and two future first-round picks to show for Harden, which is more than Houston can say to date.

The first of the four swaps the Nets sent to the Rockets never conveyed, and the next isn't likely to either. Houston selected Tari Eason at No. 17 in June with the first of its three picks from Brooklyn. The rights to the Nets' picks from 2024-27 could become incredibly valuable if Durant is traded, which amps the pressure on Nets GM Sean Marks to maximize the return. Picks could all come out in the wash if Brooklyn fetches enough, and the Nets might soon be the same frisky team they were before Kyrie Irving, Durant and Harden arrived.

And maybe that's all a front office needs to gamble its future away — the belief that it can flip player assets for draft assets and draft assets for player assets in perpetuity, so long as team ownership approves. That keeps the job alive, until you make enough mistakes that the assets are too far diminished to recoup any value.

Kevin Durant's trade value is not what the Brooklyn Nets expected. (Al Bello/Getty Images)
Kevin Durant's trade value is not what the Brooklyn Nets expected. (Al Bello/Getty Images)

The Chris Webber Metaverse

Take the Chris Webber saga, for example. Try to follow the three first-round picks that both the Warriors and Washington Bullets traded for Webber in successive seasons, and they all eventually lead to the same end.

The Orlando Magic traded Webber's rights as the No. 1 overall pick and first-rounders in 1996, 1998 and 2000 to Golden State in 1993 for Penny Hardaway, who made the 1995 Finals alongside Shaquille O'Neal.

The first two of those picks landed at No. 11 in 1996 (Todd Fuller, two spots ahead of Kobe Bryant) and No. 5 in 1998 (Vince Carter), only the Magic didn't select either, because they had dealt both to the Washington Bullets in a salary dump of Scott Skiles. The return for both picks and Skiles was a first-round pick in 1998, which Orlando used to draft Keon Clark at No. 13. They traded Clark midway through his rookie season for a first-round pick in 2000, which they traded on draft night for a first-round pick in 2006. Orlando traded that pick to Denver in 2002 to avoid the luxury tax, taking a meaningless second-rounder back in return.

(The Nuggets later packaged that 2006 pick in the sign-and-trade for Martin.)

Orlando turned two picks it could have used to draft Hall of Fame players into absolutely nothing, all to save a few million dollars over a 13-year span. The third pick in the Webber deal? Strap in, my friends.

That landed at No. 5 in 2000, and the Magic drafted Mike Miller. He won Rookie of the Year honors, before they dealt him and a future first-round pick for Drew Gooden inside of two years. They were the worst team in the league again by 2004. On the same night they took Dwight Howard atop the draft, they dealt Gooden and the 30th overall pick for the right to overpay Tony Battie as a second center. That experiment mercifully ended in 2009, when on draft night Orlando packaged Battie in a trade for ... a 33-year-old Vince Carter.

The Magic somehow turned all three of the picks they received in exchange for Webber into Carter, 13 years after they could have drafted him with one of those same picks, losing value at practically every turn. What if the Magic kept Webber? What if Hardaway's left knee never gave out? What if they drafted Carter and/or Bryant? What if O'Neal never left in free agency? Would Orlando have won the title if one or two of those things occurred? Every time they flipped the coin, it came up a loser — for five general managers.

The small-market spin cycle

This year, the Magic kept the No. 1 pick, rejecting overtures for Paolo Banchero. They're due for a winner.

Top-flight draft picks, or even picks with the chance to become top flight, are seemingly more valuable than ever, which makes the recent trend of trading excessive draft capital for complementary stars all the more curious. It just depends on where you are in the small-market cycle of trying to win or trying to lose, I guess.

The Rockets and Oklahoma City Thunder traded every player of value for a slew of picks, tanking their own draft position, too, and early returns forecast bright futures for their growing collections of lottery selections.

Hit on Jalen Green and Jabari Smith, the Nos. 2 and 3 picks the last two years, and the Rockets will have Brooklyn's trove of picks to build around either through the draft or via trade. Same goes for the Thunder, who dealt Paul George to the L.A. Clippers in 2019 for Shai Gilgeous-Alexander, five first-round picks and two swaps. They also landed Josh Giddey and Chet Holmgren in two tanking seasons since.

It's still a crapshoot, considering the flattened lottery odds and the possibility of busts and injuries, but it's really the only option the league's non-glamour markets have left. And the more coins you have to flip, the more likely one of them is going to turn up heads. That appears to be Ainge's plan in Utah, where he has reportedly offered Donovan Mitchell to the New York Knicks for six first-round picks and more prospects.

It's been nearly 40 years, but hope springs eternal the Jazz land a John Stockton and a Karl Malone in consecutive drafts. Gobert and Mitchell are the closest they've come since, and the cycle is starting again.

Once you've drafted your foundation, you better start building quickly. The player empowerment era is closing windows faster than ever. The Jazz took their swing with Gobert and Mitchell when in 2019 they traded their first-round picks from 2018-20 and multiple players for Mike Conley. It didn't work out, and they are now conceding that Mitchell will eventually leave in free agency, unless he asks out earlier.

Sometimes it's your turn to spin the wheel. The Atlanta Hawks have a five-year window before Trae Young can become a free agent — and a shorter one before his trade value diminishes in the final two years of his deal — so they bet big on Dejounte Murray, trading all of their draft capital at the tail end of Young's contract to the San Antonio Spurs. It is not dissimilar to the bet Minnesota just made on Anthony Edwards, whose rookie contract extension will expire around the time the Wolves fulfill their obligation to the Jazz.

Their plan is clear: Draft a star, leverage every asset through the first nine years of his career and maximize his title chances before unrestricted free agency. If it works, great. If not, strip the roster down to the studs and start all over again from draft scratch. Minnesota and Utah are on opposite ends of that spectrum. They don't have the luxury of using free agency as a weapon to begin anew, like the glamour markets do.

The time is now for the Utah Jazz to maximize Donovan Mitchell's trade value. (Alex Goodlett/Getty Images)
The time is now for the Utah Jazz to maximize Donovan Mitchell's trade value. (Alex Goodlett/Getty Images)

Preempting player empowerment

Identify the teams in that space between tanking and starting the cycle again, and you may find your mark.

The New Orleans Pelicans are ripe for the picking. Zion Williamson is on the clock for six years — fewer, if, like Davis, he seeks a bigger market earlier. They have Brandon Ingram, all their own first-round picks and six more left from dealing Davis and Jrue Holiday. Their turn to spin the wheel is coming sooner than later.

Same goes for the Dallas Mavericks and Memphis Grizzlies. Luka Doncic's five-year extension begins this season, and Ja Morant's starts next year. No matter how much loyalty they have shown to the franchises that drafted them, they will be leveraging their future free agencies to maximize the talent around them in short order. The Mavericks already made a bad bet on Kristaps Porzingis. They cannot afford another one.

Durant, an all-time great, may not be worth the gamble. He will soon be 34 years old, three years removed from a ruptured Achilles, having lost significant time to injury the last two seasons. His waning prime might close a team's window with a young superstar even earlier, if Durant's playoff performance opposite Jayson Tatum is an indication. That's a bet few teams, if any, will be willing to make. It is also one the Wolves may have just made for Gobert, who will be as old as DeAndre Jordan is now when Edwards turns 24 years old.

Pair Durant with Morant, and Memphis could win. Big. Or they could lose. Big. It's a high-stakes coin toss.

The Phoenix Suns and Miami Heat always made the most sense for Durant, not just because they give him the best chance to win, but also because 37-year-old Chris Paul and 32-year-old Jimmy Butler have limited shelf lives. Same goes for the Lakers, who might have to attach their last two first-round picks this decade to flip Russell Westbrook for Kyrie Irving, hastily hoping LeBron James' swan song could have a ring to it.

When an executive wants your cache of future picks, what he is really saying is, We think you're going to be terrible before the last of these picks pays off, and the best bet against that is to pair complementary young stars who can build a sustainable winner together. The Hawks spent their pick-laden package to pair 25-year-old Murray with 23-year-old Young. We can debate whether Murray was right for Atlanta's one big swing, but with youth on its side, the front office at least mitigated its risk, and that makes a gamble easier.

On the flip side of that coin, the Spurs corrected the mistake they made with Leonard, not letting Murray get close enough to free agency to depreciate as an asset. They traded Murray after his surprise All-Star debut, with two years left on his rookie extension, at the height of his value. In the process, they transferred the risk of Murray walking at the end of his deal to the Hawks, whose picks will increase in value if he does.

And maybe that's the real trend here: Small markets preempting a non-contending star's empowerment play by dealing him before the mess of a trade request and impending free agency limits the return. Turn the disadvantage of small markets, where fans are generally more understanding of the degree of difficulty it takes to win every bet necessary on the road to a championship (i.e., drafting Giannis Antetokounmpo 15th overall, acquiring Khris Middleton as a throw-in and going all in on Holiday), into a position of power.

The Jazz were almost there. They drafted Mitchell and Gobert 13th and 27th, respectively, and went all in for Conley. They were a No. 1 seed in the Western Conference, but now it's time to cut their loses at three first-round exits in four years. So, they're here now, in search of another desperate franchise, preferably one with a track record of dysfunction. It's no coincidence Ainge has New York on the other end of the line.

Remember, the Knicks can just say, "No," and that might be enough to reset this madcap pick craze.

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Ben Rohrbach is a staff writer for Yahoo Sports. Have a tip? Email him at rohrbach_ben@yahoo.com or follow him on Twitter! Follow @brohrbach

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