Lessons for a Raps team looking to make history


The Toronto Raptors are riding high heading into training camp in advance of the franchise’s 20th season. After a 48-win campaign, their second division title in franchise history, and a competitive first-round series against the Brooklyn Nets that sent the city of Toronto into a two-week frenzy, a team that looked lottery bound as recently as last December has genuine reasons for optimism heading into 2014-15.

But all that momentum also carries heightened expectations. With the heart of the 2013-14 club still intact and strengthened by the addition of some complementary free agent pieces, many will view anything short of a second-round berth as a disappointment. If the Raptors can achieve that goal, it will be the first time they’ve won a playoff series since the 2000-01 season, when a roster assembled by then-GM Glen Grunwald took the Allen Iverson-led Philadelphia 76ers to the wire in a seven-game thriller.

Grunwald worked as both vice president of legal affairs and assistant GM for the Raptors before he was promoted during the 1997-98 season, and his path to the GM’s office isn’t the only difference between his tenure in Toronto and that of current GM Masai Ujiri.

When Ujiri took over the Raptors’ front office before the start of last season, he had a roster full of question marks and lacked the flexibility required to make moves with Andrea Bargnani and Rudy Gay still on the books. Grunwald, on the other hand, found himself holding a lottery pick at the helm of a young team in need of a veteran presence. Like Ujiri, though, he also had to make a tough decision about a franchise player. Even though the respective rebuilds happened on very different terms, both resulted in very quick turnarounds for the franchise.

The Raptors won 21 and then 30 games in their first two seasons in the league. As far as expansion franchises go, they were ahead of schedule. With Isiah Thomas leading the front office and Rookie of the Year Damon Stoudamire running things on the court, the long-term future of the team looked bright. But that third season turned into a nightmare.

After a failed bid to gain majority ownership of the team, Thomas left the franchise. Stoudamire, who had grown close to Thomas during his time in Toronto, subsequently made it clear that he would not re-sign with Toronto and was traded to Portland in Grunwald’s first big move as GM. The Raptors finished 16-66 that season, and headed into the offseason with a lot of question marks.

“The team had been struggling,” Grunwald says. “We had gotten off to a bad start that year, and Isiah was such a huge part of the foundation of the team. He had a big personality and related well to the players. So much of what the players had bought into involved him being there. When he left, it created a vacuum. It made us revisit everything and rebuild from scratch again.”

Because of their poor record, the Raptors held the fourth-overall pick in the 1998 draft. Grunwald had his sights set on a dynamic player from North Carolina, but outside the draft he was also looking to change the culture of the team. With Marcus Camby and Tracy McGrady already on the roster, in addition to the incoming lottery pick Grunwald wanted to bring in a veteran presence to provide leadership in the locker room.

The player he identified was Charles Oakley, and soon after draft night, Grunwald and then-Knicks GM Ernie Grunfeld agreed to a trade that sent Camby to New York in exchange for the veteran power forward.

“We needed to bring in leadership and people who understood how to win,” Grunwald explains. “We needed someone who could lead by example and be competitive on the floor.”

Oakley had come from a winning culture in New York, and had never missed the playoffs in his 13 NBA seasons. The Raptors organization was perceived to be a mess, and Grunwald needed to assure Oakley that better things were on the horizon.

“He wasn’t particularly excited. There was a negative perception of playing for the Raptors and playing basketball in Canada that we had to overcome. We were losing and people had many reasons to not want to join our organization,” Grunwald says. “Oak’s a grumpy guy. He gave his all while he was here and I have no complaint about that. But he had reasons to be skeptical given the season we just had. We met with him after the trade and told him we were making other moves to be competitive.”

The biggest of those moves was the draft-night acquisition of Vince Carter. With the fourth pick Toronto selected Carter’s North Carolina teammate Antawn Jamison and then traded him to Golden State in exchange for Carter—selected fifth overall—and cash considerations.

Grunwald considered all his options before the deal, including trading the pick outright to acquire more proven assets, but was quickly convinced of Carter’s value.

“I fell in love with Vince when he came in for a workout,” Grunwald recalls. “We had scouted him pretty heavily. If he had returned to North Carolina for one more year, he probably would have been the first-overall pick the year after. He came in for the workout, and I got really excited because I knew we had a chance to get him where we were drafting. After that, we didn’t really seriously explore trading the pick.”

With the acquisition of a veteran power forward and a potential superstar, the Raptors were set on a new path towards contention. In Grunwald’s first full season as GM—the shortened 1998-99 campaign—Toronto went 23-27 and missed the playoffs, but spirits remained high. Carter averaged 18.3 points, 5.7 rebounds and 3.0 assists per game, and won the Rookie of the Year award. Oakley, the veteran presence the team needed, started all 50 games and played 32.7 minutes a night.

The following season, Carter launched the Raptors into the national spotlight with his remarkable display at the Slam Dunk Contest. The team carried that momentum to a 45-37 record and its first playoff appearance.

McGrady became a free agent that off-season and eventually signed with the Orlando Magic. Losing the young star is still the one move from his tenure in Toronto Grunwald thinks about most.

“We had made a max offer to keep Tracy before the start of the season, which he rejected. So that makes you a little nervous,” Grunwald says. “He was obviously a very talented player and we wanted to keep him. But the problem was—and I think Tracy would agree—that he was a bit immature at the time.”

Though the team was heading to the playoffs for the first time, Grunwald was open to trading McGrady if it meant recouping assets for the franchise before he hit free agency.

“I told Tracy and [his agent] Arn Tellem, ‘Tell me where you want to go and I’ll try and make a deal for you.’” Grunwald explains. “Arn’s a great agent but he couldn’t get any information from Tracy so everything was up in the air. We explored trade scenarios, but it never went anywhere because teams weren’t willing to give a lot for a still developing young player who wasn’t committing to re-sign with them long term.”

It was without T-Mac that the Raptors returned to the playoffs in 2000-01. But despite that unprecedented success, there was a sense that things might not last. “When T-Mac signed with Orlando, Chris Young of the Toronto Star said that, while it was a huge loss for the team, we wouldn’t feel the effects of losing T-Mac for a few more years,” Grunwald says. “And that’s exactly what happened.”

Over the next couple of seasons frequent injuries to Carter and Alvin Williams robbed the Raptors of any consistency in the regular season. The team finished with just 24 wins in 2002-03 and stumbled to a 33-49 record the year after. With two weeks left in the 2003-04 season, Grunwald was relieved of his role, putting an end to an era that started out very promising but ultimately fizzled.

So what does all this mean in 2014-15?

With the return of Kyle Lowry and the continued development of DeMar DeRozan, Jonas Valanciunas and Terrence Ross, this year’s Raptors, like the 2000-01 version, boast a core group of players with the potential to put together an extended run of winning seasons. But if Grunwald’s stint in Toronto taught us anything, it’s that teams rarely follow a consistent upward trajectory from lottery team to playoff contender to NBA champion.

The Raptors will try to convince us otherwise this season. If they can, it will go a long way to convincing Jurassic Park that Masai, Casey, DeRozan, Lowry and Co. will deliver a much better ending than the one we got from Grunwald, Vince, T-Mac and the best era in franchise history.

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