Every NBA Team's Biggest Offseason Regret
He traded for James Harden in 2012 and convinced Dwight Howard to sign with his organization a year later.
So how has Houston Rockets general manager Daryl Morey become the poster boy for NBA regret?
Pushing one's luck can do that. Morey and Co. traded away key rotation pieces Jeremy Lin and Omer Asik in a bid to create the cap space needed to sign a premier free agent—namely Carmelo Anthony or Chris Bosh. The front office then opted to let emergent forward (and restricted free agent) Chandler Parsons sign with the Dallas Mavericks, preserving flexibility and declining to match a pricey offer sheet.
Anthony and Bosh decided to stay with their respective teams, the New York Knicks and Miami Heat.
Morey snagged swingman Trevor Ariza to replace Parsons on the wing.
The Rockets took a serious step back, perhaps exiting a title conversation they had barely joined.
This is what offseason regret looks like.
To be sure, Houston wasn't the only team to miss out on Anthony. The prized free agent also toured Chicago, Dallas and Los Angeles before deciding to maintain the status quo.
And to be sure, Houston certainly isn't the only team with regrets this summer. Every team wishes something had gone a little bit differently—or will soon enough.
Here's a coulda-shoulda-woulda look around the 2014 offseason, an examination of what each team should regret most.
Atlanta Hawks
1 of 30
Biggest Regret: Missing out on Luol Deng
Lost in the mix of controversy surrounding a racist scouting report read aloud by general manager Danny Ferry is that the Atlanta Hawks were seriously interested in acquiring Luol Deng in the first place.
The free-agent forward would have been the perfect solution on an Atlanta wing currently dependent upon swingmen Kyle Korver, DeMarre Carroll and the recently signed Thabo Sefolosha. Deng would have been an improvement over that rotation, if not the kind of borderline star who might have elevated the Hawks to the next level.
Deng went on to sign with the Miami Heat, hoping to complete a lineup that still boasts Dwyane Wade and Chris Bosh in the wake of LeBron James' departure for the Cleveland Cavaliers.
Atlanta has long struggled to attract premier free-agent talent, barely registering on Dwight Howard's radar in 2013 despite serving as the superstar center's hometown.
Despite Deng's ties to Korver, the Hawks' pitch apparently wasn't persuasive enough.
In turn, this team's big addition will be the healthy return of Al Horford at the center position. Had Deng joined him, Atlanta would rank among the most intriguing teams in the Eastern Conference.
Boston Celtics
2 of 30
Biggest Regret: Not landing Kevin Love
The Boston Celtics had high hopes for the summer of 2014.
"I'm going to try to blow off some fireworks, but I have to be patient as well and we have to make sure that we don't do deals just to do deals," team president Danny Ainge told Boston sports radio 98.5 the Sports Hub in April, per ESPNBoston.com's Chris Forsberg. "We have to do the right deals. Those are a lot harder than most people think or believe or understand."
Celtics owner and CEO Wyc Grousbeck expressed similar intent, later clarifying that there had never been any guarantee his organization would do something big.
"No, if you go back and look at what I said, I said we were hoping for fireworks. I didn’t promise them," Grousbeck told The Boston Globe's Christopher L. Gasper in July. "We tried as hard as we could. July 4 has come and gone, but there is still a lot of effort and hope that eventually with all those first-round picks and other possible assets that at some point I would imagine something would happen, whether it's this year or next."
All the talk of shaking things up generated some measure of hope among fans that the club might snag disaffected forward Kevin Love, theoretically enticing the Minnesota Timberwolves with draft assets and a couple of young prospects.
In reality, the Celtics never had the best offer for Love, which became abundantly clear when the Cleveland Cavaliers ultimately parted ways with two consecutive first overall draft picks: Anthony Bennett and Andrew Wiggins.
Odds are the Celtics will continue aiming high. Hopefully they'll stop getting fans' hopes up in the process.
Brooklyn Nets
3 of 30
Biggest Regret: Losing Paul Pierce to free agency
Last season, the Brooklyn Nets proved they needed all the help they could get.
With the prospect of center Brook Lopez returning to health this season, there's every possibility the Nets could have taken a substantial step forward. That won't be easy without Pierce manning the wing and adding his clutch performances to a talented veteran mix.
Brooklyn can still count on swingman Joe Johnson, point guard Deron Williams and—to some degree—power forward Kevin Garnett.
But it's hard to imagine rookie Bojan Bogdanovic replacing Pierce at the small forward position.
In a perfect world, Pierce would be there to mentor him in his first year while holding down the starting job. In the real world, Brooklyn's lineup will be plagued by some important questions at a position that was one of its strengths in 2013-14.
Charlotte Hornets
4 of 30
Biggest Regret: Missing out on Gordon Hayward
As consolation prizes go, Lance Stephenson isn't a bad one. He brings loads of upside and innate talent to an up-and-coming Charlotte Hornets squad that was looking for some additional young help.
But Stephenson's litany of maturity issues follow him at a time when Charlotte can't afford to lose any of the chemistry it built last season.
Those maturity issues wouldn't have been a problem with Hayward.
To be sure, the Hornets did their part, offering Hayward a four-year, $63 million offer sheet that the Utah Jazz ultimately chose to match. Because the 24-year-old was a restricted free agent, Charlotte had little control over the situation.
By the numbers, Stephenson may well outpace Hayward in the grand scheme of things.
When it comes to the intangibles, however, Stephenson's arrival comes with some important questions.
Chicago Bulls
5 of 30
Biggest Regret: Losing D.J. Augustin to free agency
By and large, the Chicago Bulls can't complain about much this summer.
The club signed Pau Gasol and amnestied Carlos Boozer, upgrading the power forward spot overnight. It welcomed much-anticipated 2011 first-round pick Nikola Mirotic to the fold and drafted swingman Doug McDermott to bolster the wing with his impressive shooting ability.
The Bulls even added backup point guard Aaron Brooks to supply a spark off the bench.
But the man Brooks is replacing carved that niche out quite successfully a season ago, and Chicago may miss his contributions.
D.J. Augustin opted to sign a two-year, $6 million contract with the Detroit Pistons, leaving the Bulls without the proven sixth-man pedigree that translated into 13.1 points and 4.4 assists per game last season.
Brooks isn't a bad backup plan, but Augustin proved he could succeed in Chicago's system, having his best season since 2010-11 and putting himself on the map as a spark plug capable of energizing second units.
The 26-year-old's loss probably won't jeopardize an otherwise promising season for the Bulls, but it may be the kind of detail that quietly undermines the team's title chances.
Cleveland Cavaliers
6 of 30
Biggest Regret: Keeping Dion Waiters around
You have to be pretty picky to find fault with an offseason that included the arrivals of four-time MVP LeBron James and three-time All-Star Kevin Love.
So it's time to get picky.
In an absolutely utopian world, the Cleveland Cavaliers would trade shooting guard Dion Waiters. Beyond the suggestions that Waiters has had difficulties getting along with the rest of the Cavs—namely point guard Kyrie Irving—there's an undeniable reality that the 22-year-old is the kind of ball-dominating scorer who may not jell with a star-laden rotation.
Cleveland could use a spot-up shooter willing to do the little things to win ballgames. It could use a glue guy along the lines of the now-retired Shane Battier.
For now, Waiters doesn't sound especially interested in going anywhere.
"I'm still where I am, right?" Waiters told The Philadelphia Inquirer's Mike Sielski in August. "You can't listen to everything that's out there. I'd say 10 percent is always true. Ninety percent is not. I've been traded for three years now."
And by the sound of it, Waiters is coming into the season with the right attitude.
"I hate losing, and a guy like [James], who's probably the best player in the world right now, is someone I can learn from," Waiters added. "I can grow. I still haven't reached my peak. Now with a guy like that, he can open up the floor for you and give you a lot of opportunities."
Unfortunately, Cleveland doesn't necessarily need Waiters to reach that peak. It needs him to play a different role—or it needs someone else to play that role.
We'll extend Waiters the benefit of the doubt for now and hope for the best. Just don't be surprised if this organization opts to do otherwise before long.
Dallas Mavericks
7 of 30
Biggest Regret: Trading Jose Calderon to the New York Knicks
Granted, the Dallas Mavericks didn't trade Calderon away for nothing.
The opportunity to reacquire center Tyson Chandler was too much to pass up. The 31-year-old has a successful history with the franchise, and he instantly upgrades Dallas' interior defense in the club's bid to re-enter the championship conversation.
All the same, Calderon will be missed.
The 33-year-old Spaniard is coming off a quietly impressive season—his first and only with the Mavericks. He averaged 11.4 points and 4.7 assists, cashing in on an incredible 44.9 percent of his three-point attempts.
The even more telling point is the platoon of point guards that will now try its hand at replacing Calderon. The trio includes Raymond Felton (acquired from the Knicks in the Calderon deal), Devin Harris and longtime Orlando Magic starter Jameer Nelson.
Despite that group's collective experience, there's a lot that could go wrong. At the very least, it's hard to see any of those floor generals matching Calderon's long-range efficiency.
Thanks to the splashy acquisition of restricted free agent Chandler Parsons (and smaller moves like signing forwards Richard Jefferson and Al-Farouq Aminu), Dallas' summer was an unequivocal success. The Mavericks may even be the offseason's most improved team after the Cleveland Cavaliers.
But there's one position where that improvement may not be felt, and it's arguably the most important position on the floor.
Denver Nuggets
8 of 30
Biggest Regret: Not acquiring a star
Besides reacquiring swingman Arron Afflalo, little changed for the Denver Nuggets this summer.
The organization is banking on the belief that a healthier lineup—replete with the formerly injured Danilo Gallinari and JaVale McGee—will translate into significant improvement. In theory, those returns could elevate the Nuggets after they missed the playoffs for the first time since 2003.
While the Western Conference is as crowded as ever, the Nuggets could indeed find themselves in the playoff hunt.
As currently constituted, however, it's hard to see this team getting past the opening round anytime soon.
The roster is stocked with good-but-not-great talent, excepting perhaps point guard Ty Lawson (who often looks like a borderline star) and emergent power forward Kenneth Faried. Ideally, you'd like to see Denver swing for the fences with a trade that turned some of its exceptional depth into another legitimate star.
In July, Yahoo Sports' Adrian Wojnarowski reported that, "The Denver Nuggets have remained a strong contender for [Kevin] Love, offering a package that sources said has been the most appealing to Minnesota outside of the Cavaliers and a possible Golden State deal including Klay Thompson."
The Nuggets had the right idea.
Maybe next time they'll also have the right package of assets.
Detroit Pistons
9 of 30
Biggest Regret: Leaving the power forward position unsettled
The Detroit Pistons needed to make a choice this summer.
Greg Monroe and Josh Smith are both power forwards, and the decision to instead play Smith at the 3 spot last season was an unmitigated disaster. The 28-year-old made a career-low 41.9 percent of his field-goal attempts, including just 26.4 percent of his 3.4 three-point attempts per game.
Increased time spent on the perimeter exposed Smith's weaknesses in a big way, but Monroe's presence makes it all but impossible to ensure him significant minutes at power forward.
It's a classic logjam, and this summer did little to clarify the plan going forward. Though Smith was mentioned in trade rumors, talks obviously never got quite far enough.
Worse yet, Monroe's decision to accept a one-year qualifying offer (rather than agree to a long-term deal) complicates Detroit's ability to devise a solution. Now the prospect of trading Smith seems a bit more dangerous. If the organization parts ways with Smith and Monroe later leaves via free agency, the 4 spot suddenly becomes a position of dire need.
Stan Van Gundy may now be running the show as both team president and head coach, but the Pistons have done little to rectify an ill-conceived rotation that never panned out a season ago.
Needless to say, SVG's work is still very much cut out for him.
Golden State Warriors
10 of 30
Biggest Regret: The way things ended with Mark Jackson
It's hard to fault the Golden State Warriors for picking Steve Kerr as their coach of the future.
But that doesn't mean Jackson's tenure with the club ended smoothly.
"The unfortunate thing is I go in an office with an owner and a general manager, just us three, and while in our office it's tweeted out that I'm in a meeting and I'm about to be fired," Jackson later explained to 95.7 The Game, per ESPN.com's Ethan Sherwood Strauss. "That's not how you conduct business."
Even star point guard Stephen Curry admitted to having mixed feelings about the whole affair.
Letting a coach go after he helped turn your club around (in just three seasons) can be a tough sell from the outset, particularly when said coach is popular among his players. Allowing the details of that dismissal to get leaked before the deed is done made it more insulting.
For the record, owner Joe Lacob had a very different impression of the meeting with Jackson.
Describing the conversation to the San Jose Mercury News' Tim Kawakami, Lacob said, "It was very positive. And I think instructive for him and for us, what we both could do better maybe in another situation, another time. And I'll leave it at that."
Ultimately, we can't be sure about what happened behind closed doors, and it would be presumptuous to blindly take either side. That said, this didn't look good. As a matter of optics, the Warriors might want to do this one over again.
Houston Rockets
11 of 30
Biggest Regret: Letting Chandler Parsons walk
No big mystery here.
Houston Rockets general manager Daryl Morey elected not to match an offer sheet the Dallas Mavericks presented to Parsons, a restricted free agent at the time. Then, Morey's thinking was that the money saved by passing on Parsons could subsequently be spent on Miami Heat power forward Chris Bosh.
Shortly thereafter, Bosh decided to stay in Miami.
Morey was left hanging.
Making matters worse, the Rockets had already sent Jeremy Lin and Omer Asik packing via trade—also in a bid to clear cap space for a superstar that never came. While Houston eventually signed swingman Trevor Ariza to replace Parsons, there's little doubt this team has taken a significant step back in terms of both depth and upside.
The Parsons decision wasn't the only mistake this summer, but it figures to be the one that hurts the most.
Indiana Pacers
12 of 30
Biggest Regret: Losing Lance Stephenson to free agency
Granted, Stephenson's absence may mean one less distraction for the Indiana Pacers.
Unfortunately, his absence also means one less playmaker on a team that couldn't afford to lose offensive firepower. Even before Paul George's unfortunate injury this summer, Indiana was desperate for guys who could handle the ball, score and pass.
Stephenson did all of those things and played hard.
Now those things fall to George Hill, Rodney Stuckey and C.J. Miles—the perimeter platoon who may struggle to duplicate Stephenson's all-around production and presence.
The Pacers offense stagnated at times and ranked 22nd in offensive efficiency last season, according to Hollinger's Team Statistics.
One doesn't want to spend too much time trying to imagine what that offense will look like this season.
It's going to get ugly before it gets better—especially without Stephenson.
"I really feel bad about losing him,'' team president Larry Bird said of the 24-year-old, per USA Today's Bob Kravitz. "I hope it doesn't interfere with our relationship. But I did what I could possibly do to keep him here. Even if he didn't have any other offers, I was committed to giving him that $44 million because I believe in the kid."
We believe in him too. We think.
Los Angeles Clippers
13 of 30
Biggest Regret: No Paul Pierce-Doc Rivers reunion
It seemed meant to be.
ESPN.com's Marc Stein reported way back in May that Pierce was considering "reuniting with Doc Rivers in Clipperland in what would also be a homecoming for the Los Angeles native."
In June, Stein indicated via Twitter that, "Clippers, I'm told, believe they have real chance of stealing Paul Pierce away from Nets now that Jason Kidd no longer coaching in Brooklyn."
Instead, Pierce found his way to the Washington Wizards, where the 36-year-old instantly becomes a young team's wise, veteran guru. He would have filled a need on the wing in Los Angeles and ultimately replaces Trevor Ariza at small forward in Washington.
Meanwhile, the Clippers turned around and spent their free-agent stash on center Spencer Hawes. It was still a positive outcome for the organization, but it doesn't resonate like a Doc-Pierce reunion tour.
Los Angeles Lakers
14 of 30
Biggest Regret: Whiffing on Carmelo Anthony
The Los Angeles Lakers were the final destination on Anthony's free-agency tour this summer (prior to another meeting with New York Knicks reps), and they held out hope of landing the star forward until the very end.
Just days after the meeting in Los Angeles, ESPN.com's Ramona Shelburne and Chris Broussard reported that, "In a surprising twist, the Los Angeles Lakers have emerged as the team that most worries the New York Knicks in their attempt to re-sign superstar free-agent forward Carmelo Anthony, sources with knowledge of the situation told ESPN."
In September, general manager Mitch Kupchak told reporters that, "Our expectations with either player [Anthony or LeBron James] just based on what we perceived the environment to be...we never felt it was realistic that we could get one or [both]. But if you don't try you don't know."
Now we know.
What once seemed a distinct possibility among fans and the rest of us was apparently never "realistic" for the organization, but it was serious enough for the franchise to extend a maximum offer and pull out on the stops with a pitch that included a short film by The Matrix producer Joel Silver.
This is how the Lakers do things.
And sometimes it's not enough.
Memphis Grizzlies
15 of 30
Biggest Regret: Signing Michael Beasley
According to Yahoo Sports' Adrian Wojnarowski, it's a non-guaranteed contract.
But it's still a contract that could backfire.
Let's give Beasley the benefit of the doubt and assume his personal issues are behind him (they appeared to be last season in Miami). The real danger is that when he seduces a head coach—in this case, potentially, David Joerger—into giving him serious minutes.
Flashes of offensive brilliance, something that would appeal to the sometimes-stagnant Grizzlies, gave the Minnesota Timberwolves and Phoenix Suns hope they could salvage the once-promising prospect. In each case—and last season with the Heat—uneven focus and defensive lapses accompanied a steep decline in production.
There will always be hope when it comes to a talent like Beasley.
But there are also questions.
The Grizzlies don't seem like the kind of team that would tolerate an uncommitted defender, but desperation for scorers with star potential can do funny things to teams like Memphis—in this case a team that's also struggling to keep up with a Western Conference on the verge of leaving it behind.
This is the Grizzlies' chance to remain relevant. The big question is whether Beasley would do more harm than good.
Miami Heat
16 of 30
Biggest Regret: Losing a four-time MVP
Somehow no one cried for the Miami Heat.
LeBron James' 2010 decision had a far different effect on the national consciousness, turning every bleeding heart and otherwise non-committed fan into a Cleveland Cavaliers sympathizer. Four years later, LBJ's return to Cleveland has accordingly been perceived as some kind of karmic fulfillment.
To everyone but Heat fans, anyway.
They're left wondering if a different outcome against the San Antonio Spurs in the 2014 Finals might have made a difference. They're left praying that Dwyane Wade and Chris Bosh can turn back the clock—that Luol Deng will be enough of a "replacement" on the wing to round out a surprisingly strong lineup.
In an Eastern Conference where only the Cavaliers and Chicago Bulls seem destined for greatness, the Heat remain something of a dark horse to enter the title conversation. Miami wouldn't last long in the West, but it has a chance to make some noise in the East.
Even without the best player in the cosmos.
Milwaukee Bucks
17 of 30
Biggest Regret: Prolonging the O.J. Mayo experiment
Mayo is coming off a bad season—by his or any other standards.
His pathetic 11.27 player efficiency rating speaks volumes. So do his 40.7 shooting percentage and a plummeting assist tally.
In fairness, Mayo battled some injuries last season, missing 30 games altogether. And in fairness, this is empirically what happens when Mayo comes off the bench. His best seasons in Memphis and a strong season in Dallas correlated with starting jobs.
When Mayo was benched with the Grizzlies, his efficiency bottomed out—hitting marks conspicuously similar to last season's. For whatever reason, he's been far more steady as a starter, and it's unclear that he'll have that opportunity in Milwaukee.
If the 2013-14 campaign was an outlier, the Bucks will thank themselves.
Otherwise, though, you have to figure it's only a matter of time before the organization sends the still-talented shooting guard on his way. A change of scenery could do wonders for the 26-year-old.
Mayo was the third overall pick in 2008 and has shown flashes of excellence. But it hasn't all been pretty.
Minnesota Timberwolves
18 of 30
Biggest Regret: Going forward with the Ricky Rubio era
This is a mistake.
Or anyway, it's about to be one.
The Pioneer Press' Charley Walters recently reported that, "Rubio's representation has been seeking a five-year maximum contract that could be worth about $75 million. The Wolves are willing to wait if Rubio decides a four-year deal isn't enough."
This is crazy talk. The Minnesota Timberwolves shouldn't even be thinking about paying Rubio that kind of money, not without a credible jumper. And not with four more years and $48 million of Nikola Pekovic on the books.
Minnesota had a brilliant summer all things considered. Kevin Love was destined to leave one way or another, but team president and head coach Flip Saunders got two No. 1 overall picks in the deal (in Anthony Bennett and Andrew Wiggins). He also—separately—traded to acquire Thaddeus Young from the Philadelphia 76ers.
Add rookie Zach LaVine and veteran Mo Williams to the mix, and you have a team that could be pretty fun to watch.
It's tempting to envision Rubio as the conductor at the heart of it all, but this kind of financial commitment can break a franchise. In a league that's full of good point guards, Minnesota could find a replacement that yields a superior return on investment—if not now, soon.
Instead, the organization is in talks to extend Rubio and will probably retain his services—whether it's codified now or in 2015.
And the Timberwolves will have 75 million reasons to hope it works out.
New Orleans Pelicans
19 of 30
Biggest Regret: Keeping Eric Gordon around for the long haul
Isn't it about time for the New Orleans Pelicans to deal Gordon to the Indiana Pacers—or anyone, really? Hasn't this been the conventional speculation for well over a year now?
Besides the fact that Gordon never really seemed like he wanted to stay in New Orleans, there are some X's and O's reasons to prefer someone else. If the Pelicans could—for example—land a starting small forward, that would create space for Tyreke Evans to start at shooting guard (where Gordon currently plays).
Positions are overrated in today's league, but the point is Evans and Gordon are to a large degree redundant—both equipped to guard similar players and both in need of handles and touches on the perimeter.
When given a starting opportunity and increased minutes late in the season, Evans shined—averaging 20.4 points, 6.7 assists and 5.3 rebounds per game in March. It was the kind of run that harkened back to the 25-year-old's emergent rookie year.
It was the kind of run that suggested the time to part ways with Gordon had come.
New York Knicks
20 of 30
Biggest Regret: Somehow not getting Steve Kerr
It seemed inevitable.
Kerr was the perfect extension of all things Phil Jackson, a trusted affiliate of The Jackson Empire who could stand on his own two feet and hedge against any perception that the Zen Master was also a master puppeteer.
When Kerr took his talents to the Golden State Warriors instead, Jackson experienced the kind of defeat he rarely encountered stalking the sidelines of superstars. It was an early blow to a still nascent legacy running the show with the New York Knicks.
A legacy that rebounded nicely on account of a Derek Fisher Plan B and the subsequent retention of star forward Carmelo Anthony.
To be sure, Fisher should be fine—maybe better than Kerr for all we know at this point.
The real harm done here is to things like prestige and leverage, the sense that this organization is still a premier destination, one that's rediscovering its luster under Jackson's leadership. Kerr's preference for the Warriors spoke volumes about the league's new balance of power.
And where Jackson finds himself therein.
Oklahoma City Thunder
21 of 30
Biggest Regret: Trusting that Scott Brooks has this figured out
It clearly isn't fair to blame Brooks for everything.
His team advanced to the NBA Finals in 2012 and has made two separate appearances in the conference finals over the last four seasons. Injuries (to Russell Westbrook in 2013 and to Serge Ibaka last season) have played central roles in interrupting OKC's otherwise impressive postseason marches.
Few coaches—including those who've been on the job far longer than Brooks—can boast those kind of accomplishments.
On the other hand, Brooks was dealt quite a hand. With two of the league's 10 best players on his roster, expectations are understandably unyielding.
And the bigger concern is that the 49-year-old has engineered a simplistic offense that almost certainly relies too heavily on the heroics of Westbrook and 2014 MVP Kevin Durant. It's the kind of formula that may be just good enough to remain in the title conversation—and just one-dimensional enough to thwart a title.
Oklahoma City could find a better coach.
Chances are it won't—not yet, anyway.
As The Oklahoman's Berry Tramel put it regarding the head coaching gig, "The Thunder is not a reactionary organization. The Thunder doesn't make rash decisions. Doesn't give in to popular demand."
That's all well, good and admirable. But this is an organization with a great deal at stake. With Durant facing free agency in 2016, now's the time for OKC to prove it's his best chance at a championship.
Now's the time to prove it has a coach who can take him there.
Orlando Magic
22 of 30
Biggest Regret: Handing Channing Frye $32 million
For almost any other team, the four-year, $32 million Channing Frye signed this summer might have made a lot of sense. The 31-year-old stretch 4 is in his prime and adds a valuable dimension to any club's ability to space the floor.
The problem is the Orlando Magic are nowhere near their collective prime.
This is a young team with tons of growth ahead of it. Frye doesn't make a lot of sense given its trajectory. He seemed primed to help a playoff team take the next step, but his services can only take the Magic so far.
And in the meantime, they'll come at the expense of minutes that would otherwise help groom young forwards like Tobias Harris, Maurice Harkless, Andrew Nicholson and rookie Aaron Gordon. In the spirit of rebuilding, you'd like to see those guys get as much opportunity as possible.
Frye's presence will stunt some of that development and cost a pretty penny in the process.
Philadelphia 76ers
23 of 30
Biggest Regret: Acquiring Dario Saric on draft night
Saric may well turn out to be a fine NBA player, but the Philadelphia 76ers won't reap any benefits from him anytime soon. He remains at least two years away from joining the league, at which point he could help extricate the Sixers from a rebuilding process they'll probably still be undergoing.
After selecting Joel Embiid—who could miss the entire season—with the third overall pick in June, it would have been nice to bring someone else aboard who could yield immediate dividends and give brutalized fans something to anticipate.
Indeed, Elfrid Payton—who Philly originally selected with the No. 10 pick before striking a deal with the Orlando Magic—would have been precisely such a player.
And chances are he would have fit alongside point guard Michael Carter-Williams just fine.
Instead, the 76ers went all in with a trajectory that likely entails another one or two seasons of outright tanking. There's certainly a logic to that strategy, but there's also something to be said for bringing young guys into the system sooner rather than later. If this team's ever going to develop sound chemistry, it needs to start implementing a consistent rotation and allowing key pieces to evolve together.
Without Saric entering the equation until 2016 or 2017, this is still very much a work in progress.
Phoenix Suns
24 of 30
Biggest Regret: Playing hardball with Eric Bledsoe.
Eventually, everything worked out between the Phoenix Suns and Eric Bledsoe.
And while a five-year, $70 million contract may resolve any lingering tensions, the failure to quickly and definitively lock up the restricted free agent may have left some scars.
Though Bledsoe remained quiet for most of the summer, in July he told WVTM Birmingham's Kyle Burger, "First off I'm going to let my agent handle it. I can understand the Phoenix Suns are using a restricted free [agency] against me. But I understand that."
For the record, many felt Phoenix's initial offer of four years and $48 million was more than enough.
The Arizona Republic's Paul Coro reported in August that, "Four current NBA executives and two prominent agents were anonymously unanimous in their belief that the Suns made a fair offer to Bledsoe and that he does not merit a maximum-salary contract now."
But Bledsoe's camp never saw it that way. It felt like the Suns were exploiting a lack of market competition to essentially lowball Bledsoe and hope for some kind of discount.
Maybe it won't matter.
The danger is that Bledsoe won't feel fully invested in an organization that fully invested in him only after months of stalled negotiations.
Portland Trail Blazers
25 of 30
Biggest Regret: Not signing LaMarcus Aldridge to an extension
The Portland Trail Blazers didn't have much control over this one.
ESPN.com reported in July that, "All-Star forward LaMarcus Aldridge has told the Portland Trail Blazers he won't sign a contract extension this offseason but plans to after the 2014-15 season, saying he wants to surpass Clyde Drexler as the franchise's greatest player."
The decision certainly doesn't guarantee the 29-year-old will depart via free agency in 2015.
If anything, Aldridge has alluded to the opposite.
"I'm happy to stay, happy to be here, happy with the direction the team has gone the last year or two," Aldridge told The Oregonian's Joe Freeman in July. "This has no impact on my interest in staying in Portland. I just want to get a five-year deal. I feel like that's the best decision on my part."
Indeed, Aldridge's primary motivation for entering free agency may be to secure a more lucrative deal—earning more years and more dollars than he would by signing an extension this summer.
That said, there remains a very real chance that the eight-year veteran could change his mind. Should the Trail Blazers take a step back—which is always possible in a Western Conference that isn't getting any easier—Aldridge may reluctantly opt to explore his options.
From there, anything is possible.
Sacramento Kings
26 of 30
Biggest Regret: Signing and trading Isaiah Thomas to the Phoenix Suns
It's hard to make sense of the Sacramento Kings' willingness to part ways with 25-year-old point guard Isaiah Thomas. Were he asking for a ridiculous amount of money, that would be one thing.
On the contrary, however, Thomas agreed to a deal that will pay him just $28 million over the next four years.
For a guy coming off a breakout season in which he posted a career-high 20.3 points per contest and achieved an impressive 20.54 player efficiency rating, that's a bargain of a deal—one the Kings certainly could have afforded.
Meanwhile, Sacramento has replaced Thomas with a platoon of Darren Collison and Ramon Sessions. It's a Band-Aid solution that should prevent a disastrous collapse of head coach Mike Malone's backcourt, but it's probably not an upgrade over Thomas.
San Antonio Spurs
27 of 30
Biggest Regret: Missing out on Pau Gasol
The San Antonio Spurs will bring back a roster that's coming off a championship, so it's hard to view the summer as any kind of failure.
For a minute there, though, the organization was one of a few teams in the running to sign free-agent big man Pau Gasol—who instead decided to take his talents to the Chicago Bulls. It's easy to imagine the Spaniard joining forces with the internationally flavored Spurs, adding star-caliber depth to an already solid front line.
Such a coup would have been San Antonio's most momentous free-agent acquisition in some time—perhaps since snagging a veteran iteration of Michael Finley away from the rival Dallas Mavericks back in 2005.
The Spurs aren't known for splashy summers, so 2014's was pretty par for the course.
But Gasol would have been the kind of splash that made perfect sense for a franchise aiming for its first repeat title.
Toronto Raptors
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Biggest Regret: Going on a point guard spending spree
The Toronto Raptors reached agreements with both of their free-agent point guards this summer: starter Kyle Lowry and reserve Greivis Vasquez.
When either deal is viewed by itself, it doesn't seem especially extravagant. Lowry agreed to a four-year deal that will pay him $48 million, while Vasquez will make $13 million over the course of the next two seasons. Neither deal breaks the bank on face.
Viewed together, however, the expenditures mean Toronto will spend over $18 million next season on a tandem on point guards who have probably plateaued in their respective evolutions. They weren't good enough to lead these Raptors to a conference semifinals appearance last season, and it's hard to see that changing.
To its credit, the Raptors front office—helmed by general manager Masai Ujiri—has demonstrated a clear commitment to maintaining some continuity after a breakout season in which the club claimed the third seed in the Eastern Conference.
There's something to be said for that.
But there's also something to be said for fiscal discipline. This was a steep price to pay for a one-two punch that still has something to prove.
Utah Jazz
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Biggest Regret: Drafting Dante Exum
Sure, it's far too soon to declare Dante Exum a bust.
But the Utah Jazz could have taken a safer route by selecting a guard like Marcus Smart or Nik Stauskas with the No. 5 overall pick. Exum's ostensibly high ceiling ultimately earned him the nod, but it's awfully hard to say when the 19-year-old will be ready to make significant and consistent contributions at the NBA level.
For a team that won just 25 games last season—worst in the Western Conference—it's difficult to get excited about a waiting game.
Exum struggled mightily during summer league play, averaging 7.2 points, 2.8 assists and 2.6 rebounds while shooting just 30.8 percent from the field in 26.6 minutes per contest. For every flash of brilliance, there were several reminders that the Australian prospect is still a ways away from discovering his potential—whatever that potential might be.
The Deseret News' Jody Genessy summarized the early results during summer league, writing, "In his first four games, the 19-year-old has shown glimpses of greatness with keen court vision, playmaking skills and a better-than-expected defensive ability. But he’s also exhibited rawness, inexperience, shooting struggles and fatigue-induced limitations."
The Jazz could very well have the last laugh.
But it doesn't look like that'll be the case anytime soon.
Washington Wizards
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Biggest Regret: Losing Trevor Ariza
Don't get me wrong. There's plenty to like about the Washington Wizards replacing Trevor Ariza with Paul Pierce.
Pierce is a future Hall of Famer, a ready-made leader who could pay significant dividends on an otherwise youthful roster in need of guidance. But he's also 36 years old and won't duplicate Ariza's quickness and perimeter defense.
Moreover, the Wizards built promising chemistry a season ago, and Ariza was a big part of that. In his second season with the franchise, he averaged an impressive 14.4 points and 6.2 rebounds per game, signaling the ability to bring some consistency to his complementary role on Washington's wing.
Coming off a breakout season in which the Wizards advanced to the conference semifinals, you'd like to have seen the organization keep everyone together. It did just that with respect to center Marcin Gortat, but there was less willingness to spend on Ariza.
Pierce may ease the blow, but this could also be the kind of decision that comes back to haunt a team that was on the right track a season ago.
