Watching the NBA Finals always carries a bit of pain for the NBA general managers who are not directly involved, but it can be especially bitter when the action includes players they could have drafted.
"Everyone has at least a couple [of players they missed out on in the draft] if they've done the job for any time at all," said Wally Walker, who spent 12 seasons as president and GM of the Seattle SuperSonics. "The ones that hurt the most are the ones you had great conviction about and, for whatever reason, ended up not taking them."
And no player prompts more what-ifs, seemingly, than the San Antonio Spurs' Tony Parker. Of the four former GMs willing to discuss the players that make them squirm for not having selected them, three mentioned Parker.
The Spurs selected Parker with 28th pick in the 2001 draft, the last pick of the first round. He has been part of four championship teams. Only five players taken ahead of him have any championship rings—No. 2 pick Tyson Chandler, No. 3 pick Pau Gasol, No. 4 pick Eddy Curry, No. 6 pick Shane Battier and No. 20 pick Brendan Haywood—and only Gasol can claim being an integral part of more than one title run.
"Tony Parker was one for me, for sure," Walker said.
The SuperSonics selected stretch power forward Vladimir Radmanovic with the 12th pick and point guard Earl Watson with the 39th pick in 2001. Considering they already had a nine-time All-NBA selection in Gary Payton as their floor general, they certainly weren't the most desperate of the 20 teams that passed on Parker that year, and they did land a 13-year point guard in Watson.
Walker coveted Parker so much, though, that he tried to pry him away from Spurs GM R.C. Buford the following season.
"We had him in for a workout before the draft, and he was terrific in every way," Walker said. "We all had great conviction about him. Could we have taken him at 12? Sure. But we already had Gary."
Parker haunts Garry St. Jean as well. St. Jean served as the Golden State Warriors' GM from 1997 to 2004. In 2001, he had two first-round picks, taking shooting guard Jason Richardson fifth and power forward Troy Murphy 14th. He then took point guard Gilbert Arenas at No. 30, two slots after Parker.
St. Jean and Parker share a French heritage, and Parker showed a deep familiarity with St. Jean's roots. St. Jean was smitten, but Parker had a pulled hamstring when he made his predraft visit and couldn't work out.
That, combined with Parker being a scrawny 19-year-old and playing a position foreign players had not proved they could handle in the NBA, made it hard to justify taking him in the top half of the draft. "We were all set to take him with that second-round pick," St. Jean said. "I loved him."
So did Larry Riley, who had stints as the GM of the Warriors (2009-2012) and as personnel director for the Vancouver Grizzlies (1994-2000). In 2001, he was an assistant coach with the Dallas Mavericks, who lost out on the chance to take Parker because they traded their first-round pick (No. 22 overall) in a deal made the previous year for guard Courtney Alexander. Thirty-eight games into his rookie season, the Mavs traded Alexander to Washington.
If Riley, now director of scouting for the Warriors, needs anyone to commiserate over draft misses, he can reach out to the team's new head coach Steve Kerr, who spent three years as the Suns' GM (2007-2010).
In his first draft, he had two late first-round picks, Nos. 24 and 29, using them on Spain's Rudy Fernandez and small forward Alando Tucker, respectively, before quickly dealing Fernandez to the Portland Trail Blazers (along with James Jones) for cash. Tucker spent almost his entire career on the Suns' NBA Development League team before being dealt to Minnesota.
That's why Kerr winces every time he sees Arron Afflalo, who went 27th to the Detroit Pistons and is now the Orlando Magic's starting shooting guard. "We had Raja Bell, and Arron reminded us a lot of him," Kerr said. "Toughness, three-point shooting. We ended up going with need and took a small forward."
Much like St. Jean's reluctance to take Parker without seeing him work out, Kerr also passed on Chicago Bulls power forward Taj Gibson in the 2009 draft. "Taj was there when we picked, but we couldn't get him to work out for us," Kerr said.
The Suns were also in search of a stretch-4, and Gibson was primarily a rebounder when he entered the league; that is why Kerr chose to take Earl Clark with the 14th pick. "Taj obviously has had the better career and would've been the better pick," Kerr said.
Indeed, no GM has but a single bad memory.
St. Jean's other regret came in his first year on the job: not taking Paul Pierce.
"No doubt about it," St. Jean said. "I can still remember his workout and then sitting with him afterward. He had ties to the Bay Area and told us he'd love to play there. That's a big coulda-woulda-shoulda."
Owner Chris Cohan was adamant that the team make a high-character pick, what with the franchise's travails surrounding Latrell Sprewell choking coach P.J. Carlesimo still fresh in everyone's mind. Pierce, born in Oakland and raised in Inglewood, California, had a few questions raised about his work ethic, and that was apparently enough to dissuade Cohan.
So the Warriors took Vince Carter with the fifth pick in 1998 and flipped him to Toronto for the No. 4 pick: Antawn Jamison. Boston Celtics team president and coach Rick Pitino couldn't believe Pierce was there to be taken with the 10th pick. With the four teams following the Warriors taking players at other positions, the Celtics called to find out why St. Jean would take Jamison over Pierce if he wanted a small forward.
"They called and asked, 'Is there something wrong with him?' They were bewildered," St. Jean said.
Pitino assuredly had his regrets for taking Ron Mercer and leaving Tracy McGrady for the Toronto Raptors in the 1997 draft, but that wasn't the case when he tabbed Pierce a year later.
As Walker noted and St. Jean, Riley and Kerr all echoed, every GM has had picks he'd like to have spent differently. The job is not as easy as it might appear from the fans' view, which is simply to take the best available talent.
The desires of ownership, the existing structure of the team and a lack of cooperation from either a player or agent can all play into the choice a franchise makes. And as these four understand, there's only one chance to make the pick. Once hindsight determines if they were right or wrong, every GM also understands that he must take responsibility for every selection he makes, for better or worse.
Ric Bucher covers the NBA for Bleacher Report.
Follow him on Twitter: @RicBucher
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