On May 31, 2013, the Toronto Raptors hired Masai Ujiri as the team’s new general manager. It took him all of six weeks to expunge the cardinal memory of the previous regime.

Bryan Colangelo had an up-and-down run as the team’s general manager, and while he made some savvy moves during his tenure, a complete lack of tangible forward progress on the court ultimately led to his ouster. The franchise is still enjoying his acquisition of Kyle Lowry for a first-round pick that became Steven Adams (after contributing to a James Harden acquisition). The team is still getting great value out of the extension Colangelo signed DeMar DeRozan to, one that was thought to be an overpay at the time. And Colangelo was responsible for drafting Jonas Valanciunas, who looks set to justify his fifth-overall status here in his fourth season.

But Colangelo made mistakes, one of which he couldn’t help but to double-down on.

The 2005-06 Raptors finished 27-55, fifth-to-last in the NBA. Colangelo didn’t have much of a hand in that team, having only signed with the Raptors in late February. With only an 8.8-percent chance of winning the draft lottery, the basketball gods smiled fondly on Colangelo, blessing his tenure with a gift: The No. 1 overall pick in the 2006 NBA Draft.

The 2006 draft didn’t have a consensus top pick. Of all the seasons to land at No. 1 – and there’s never a bad time to get the top pick, to be clear – this was one of the most difficult imaginable. A collection of eight different mock drafts had five different players as potential top-three picks, and they ranged from established college stars (Adam Morrison), to risky with high upside (Tyrus Thomas), and somewhere in between (LaMarcus Aldridge). Even Rudy Gay, who would be selected eighth, was a top-three pick on several mocks, having fallen from consensus No. 1 pick status. Brandon Roy was probably a justifiable pick, too, though he didn’t land top three on any final mocks.

On June 28, 2006, Colangelo made an indelible footprint on the history of the franchise, selecting Italian big man Andrea Bargnani first overall.

In that moment, Colangelo proved himself willing to take risks, if nothing else. DraftExpress called the pick “a risky move that very few GMs in the NBA would have had the guts to make.” ESPN’s Chad Ford loved the pick, writing, “Colangelo isn’t afraid to go against the grain, and no one in the NBA knows Bargnani better.”

The pick didn’t exactly work out.

To date, Bargnani ranks 50th among 69 No. 1 overall picks in total career win shares and 56th in win shares per-48 minutes. The Raptors whiffed, with Bargnani failing to ever live up to his potential as a versatile, high-efficiency offensive weapon capable of at least protecting a rim on defense. He showed flashes of potential, even for long stretches, nearly earning an All-Star appearance at one point (no one man should have all that pasta). He hasn’t even turned out a bad NBA player, as he’s now in his 10th season and has averaged 15 points at near league-average offensive efficiency. But “capable one-way bench cintributor” is not the preferred outcome for a top pick, and Bargnani ranks 11th from his draft class in total win shares (and 27th on a per-minute basis).

He was unquestionably the wrong pick. Aldridge was the choice in hindsight, Gay would have been fine (Colangelo would, of course, get Gay eventually, another mistake Ujiri remedied early in his tenure), and Roy would have been great until he wasn’t. Heck, Lowry may be the second- or third-best player from that draft, and he went 24th overall (nobody nailed this draft – Paul Millsap went in the second round, Rajon Rondo outside the lottery, and six of the top 10 picks are out of the NBA).

What was worse than the pick, which was an understandable gamble, was chasing bad money with good. On July 8, 2009, the Raptors signed Bargnani to a five-year, $50-million contract extension. Bargnani was coming off of a solid third season that saw him average a then-career-high 15.4 points and sink 40.9 percent of his threes. His shot-blocking had improved, too, as he was tethered a bit more closely to the rim, but he remained an appreciable negative on the defensive end.

The extension was a bet that Bargnani’s progress would continue in linear fashion, his age-23 season a harbinger of another breakout forthcoming. It was a risk, like the pick, but a less necessary one. The Raptors could have waited out his fourth season and then either paid based on realized potential or avoided overpaying if his development stalled. That approach would have run the risk of having to pay him even more in restricted free agency in 2010, but that was a more reasonable gambit than paying for production that wasn’t there yet.

Bargnani’s development continued on an uneven path. With a larger workload in 2009-10, his numbers improved slightly. 2010-11 was his “breakout” season, as he averaged 21.4 points, but his scoring efficiency cratered, his shot-blocking vanished, and he became even less of a rumor on the glass. Save for the famous “13-game stretch,” there was serious cause for concern. Things got worse in an injury-plagued 2011-12 season (he began to pass more willingly and got to the line a lot more, but he shot terribly and his defense was woeful), which was followed by an injury-plagued 2012-13 campaign.

Enter Ujiri and the New York Knicks.

On July 10, 2013, the Raptors flipped Bargnani and the $23.4 million owed to him over two years to the Knicks. The return was small in on-court terms: A deep reserve in Steve Novak, a retiring Quentin Richardson, and a bought-out Marcus Camby. But the Raptors also landed a 2014 second-round pick (originally from the Thunder and later sold to Brooklyn, it was No. 59 and became Xavier Thames), a 2017 second-round pick (later sent to Utah to unload Novak for Diante Garrett), and a 2016 first-round pick.

It’s now the 2015-16 season, which means that first-round pick – which, again, the Raptors received for two years of an overpaid, injury-plagued disappointment – will convey this summer. The 2016 NBA Draft isn’t expected to be a great one, but in a rising salary cap environment, the relative value of players on rookie scale contracts is significant. If the salary cap jumps as expected, next year’s No. 1 pick would take up 6.6 percent of his team’s salary cap instead of the 8.2 percent Karl-Anthony Towns is taking up this season (these figures assume the standard 120 percent of rookie scale). The No. 20 pick will take up less than two percent of a team’s cap space. Static rookie salaries in a rising cap environment make hitting on a pick this year (and the last two) even more valuable in the short-term than normal.



But there’s a catch with the Raptors receiving the Knicks’ pick this summer: They may receive Denver’s instead.

While Ujiri was still with the Nuggets, he helped engineer the Carmelo Anthony trade. Part of that deal landed the Nuggets the right to swap picks with the Knicks in 2016, which means that Denver will have “dibs” on the Knicks’ pick. The Raptors technically own “the less favorable” of Denver or New York’s picks, which still isn’t the worst position to be in.

Raptors fans, then, can watch the standings with an eye on both New York and Denver. We’ll be adding a “pick tracker” to the site to help with this, so readers can quickly look up what the 2016 draft looks like for Toronto. Should New York or Denver make the playoffs, the Raptors won’t be picking in the lottery, but there’s a non-zero chance neither the Knicks nor Nuggets make the postseason. That may actually be the most likely outcome.

The Knicks are better than a season ago, but they should still come up short of the playoffs. They have a healthy Carmelo Anthony now, added Kristaps Porzingis and Jerian Grant in the draft, and brought in sold two-way contributors in Robin Lopez, Arron Afflalo, and Kyle O’Quinn. I quite liked their modest offseason, and I have them down for a low-30s win total, a nice improvement but not quite enough. The Nuggets, meanwhile, are looking one or two years down the line, with nice pieces in place (Danilo Gallinari and Wilson Chandler are now locked up on reasonable extensions) and an intriguing rookie point guard in Emmanuel Mudiay. Having “nice pieces” in the Western Conference doesn’t get you much, and so the Nuggets are a long-shot to land in the playoffs.

In all likelihood, the Raptors have a lottery pick coming their way this summer.

There’s one other necessary caveat to pay attention to: The Nuggets have the right to swap picks after the lottery. So the Raptors don’t have a chance at the No. 1 pick. Denver essentially owns New York’s ping-pong balls. There are 91 possible in-lottery standings iterations for the two teams, ranging from finishing 29th and 30th – the Raptors would have a 12.84-percent chance at the No. 2 pick – to finishing 17th and 18th – the Raptors would have a 0.006-percent chance at the No. 2 pick – but posting all of them would be insane (it’s a lot of multi-conditional probability and makes my head hurt). Those are numbers we can crunch come lottery time, but for now simply rooting for the Knicks and Nuggets to be bad will suffice.

So keep an eye out for the tracker to pop up on the site and remember: For as frustrating as his time with the team was and as much residual disappointment may still exist, Bargnani at least left the Raptors a likely lottery pick on his way out the door.