When the Toronto Raptors eliminated the Milwaukee Bucks over the weekend, TSN’s Josh Lewenberg wrote that Kyle Lowry was the first player to lift the franchise’s one and only conference championship trophy and carried it into the locker room when the team eventually left the confetti-draped court. Teammate Fred VanVleet said he saw Lowry “tearing up a little bit” and as the team’s longest-tenured player by several seasons, Lowry knows a thing or two about what the franchise has been through.

There’s been quite a lot of ups and just as many – if not more – downs. But after all that, here they are in the championship. With the franchise set for their first Finals appearance in their 24-year history, TSN.ca takes a look at their playoff successes, failures and everything in between.

 

Growing up as a franchise

1995-2003

As most expansion teams do, the Raptors struggled mightily through their first few seasons, winning a combined 67 games in their first three years. But help finally came in the form of a draft-day trade that landed the franchise Vince Carter. The North Carolina product won Rookie of the Year in a lockout-shortened season and set the stage for Toronto’s first playoff appearance a season later.

Coming off a 45-37 regular season in 1999-2000 – their first winning record in team history – the Raptors were matched up against the New York Knicks in the best-of-five opening round. But it was clear they weren’t quite ready yet. Despite three close games, Toronto was swept, losing the decider in their first ever home playoff game. Head coach Butch Carter was fired after the season and replaced by Lenny Wilkens.

With playoff experience under their belt, a new coach and the up-and-coming duo of Carter and cousin Tracy McGrady leading the way, there was optimism about what was next. Except McGrady left for the Orlando Magic once his rookie deal ran out and the Raptors were forced to rely on Carter and Carter only as the centrepiece of the franchise in 2000-01. Come playoff time, the Raps were matched up against those same Knicks once again. This time, the series belonged to Toronto after they eliminated the Knicks on their home floor in a do-or-die Game 5.

Next up was Allen Iverson and the Philadelphia 76ers. Raptors fans know this one – with the series tied 3-3, Carter and the Raptors were in Philly for Game 7. Except the day of the game was the same day Carter was scheduled to graduate from North Carolina. Fulfilling a promise to his mom, Carter decided to attend his ceremony and fly back to Philadelphia hours before tip-off. Naturally, things would go right down to the wire and it was Carter at the centre of it all. The Raps trailed the 76ers by one and had the ball in the frontcourt with exactly two seconds remaining. Dell Curry inbounded the ball and hit Carter running right to left. Defender Tyrone Hill bit on a shot-fake and Carter was left with a rushed but relatively wide-open shot at winning the series. Clank. The shot was right on line but a little bit long and Philly survived to win the series by inches.

 

After the game, Carter’s decision to attend his ceremony appeared to draw the ire of teammates.

“I’m not the right person to answer that,” teammate Chris Childs told reporters after the loss.

Years later, Carter stood by his decision.

Things were never really the same after the loss to the Sixers. Toronto made it back to the playoffs the year after but fell in the first round to the Detroit Pistons. Things fell off the rails the next year. Wilkens was fired following a 24-58 record in 2002-03 and it wasn’t long until a disgruntled Carter was traded to the New Jersey Nets for a package of players that didn’t come close to matching his output.

How different might everything have been if Carter’s shot was a few inches shorter?

 

Transition years

2003-2010

Once Carter was traded, the city was looking for a new star. Enter Chris Bosh, who was selected fourth overall the season before out of Georgia Tech. Like the Carter-McGrady era, things started off promising. Bosh made his first All-Star Team in 2006 and a year later led the team to their first Atlantic Division title, ending a four-year playoff drought in the process. And how’s this for drama – Toronto’s first-round opponent in the spring of 2007? Carter’s Nets.

The buzz was back in Toronto but it ended quickly. The Raps had home court advantage and gave out red T-shirts to the home fans in Game 1, turning the Air Canada Centre into a sea of red. The only problem was New Jersey wore their alternate red uniforms and made the home crowd cheer against the very colour they were wearing. Toronto lost the opener and eventually the series in six games.

The Raps took a step back during the 2007-08 season to finish at 41-41, but thanks to a top-heavy Eastern Conference they went into the playoffs as the sixth seed. They drew the Orlando Magic and rising-star Dwight Howard, who quickly ascended to becoming one of the most popular players in the NBA – hardly an easy opening round pairing.

 

Howard was an absolute monster in that series, averaging 22.6 points a game and 18.2 rebounds as Orlando blew away the Raptors in five games.

“[Howard] is a phenom,” Bosh said following their elimination in Game 5. “He is the best centre in the league.”

The Raps tried to get Bosh some help in the years that followed with high-profile additions like Jermaine O’Neal, Shawn Marion and Hedo Turkoglu, but the moves never translated into success. Despite more All-Star seasons from Bosh, the Raptors missed the playoffs in each of the next two seasons and Bosh joined the Miami Heat as a free agent. Just like the Carter era, fans were left wondering what could have been.

 

Laying the groundwork

2010-2014

Things got a lot worse in Toronto before they got better. The team combined to win just 45 games in the two seasons after Bosh’s departure.

But signs of continuity started to show. The team drafted DeMar DeRozan in 2009 and he quickly emerged as the focal point of the offence with Bosh out of the picture. Dwane Casey took over from Jay Triano as the team’s head coach following a successful stint as an assistant coach with the Dallas Mavericks. In the summer of 2012, the Raptors pulled off a deal with the Houston Rockets to land point guard Kyle Lowry. The following May, Toronto hired Denver Nuggets general manager Masai Ujiri as the team’s new GM.

Results didn’t show right away, but Toronto’s win total went up every season from 2011 to 2014. In December of 2013, the Raps reached a crucial turning point.

In his first major move, Ujiri dealt struggling star Rudy Gay to the Sacramento Kings in a multi-player deal. Call it luck, addition by subtraction or a combination of both, but the trade was a turning point. Not just for the season, but for the franchise. Toronto was 7-12 at the time of the trade but finished the regular season at 48-34 which was their best record in franchise history at the time.

For the first time in five seasons, the Raps were headed to the playoffs. Standing in their way was a star-studded Brooklyn Nets team who some feel intentionally dropped to the No. 6 seed to draw a matchup with the Raptors. Despite a close first-round series that came down to the dying seconds of Game 7, the move worked. Brooklyn took the decider by one point. 

 

Looking for a breakthrough

2015-2018

After a new franchise record in wins (49) during the 2014-15 regular season, the Raptors were back in the playoffs against the Washington Wizards. But things were a lot more one-sided than the year before.

After he said the Raptors lacked an ‘It’ factor, Paul Pierce made a series of clutch shots to help the fifth-seeded Wizards sweep the Raptors. They went quietly, too, losing Game 4 by 31 points.

 

But the Raptors stayed the course and, for the third year in a row, had their best season ever in 2015-16. They won a team-high 56 games and knocked off both the Indiana Pacers and Miami Heat in the first two rounds. Little did they know they were about to meet their greatest obstacle yet.

Facing LeBron James and the Cleveland Cavaliers in the conference finals, the Raps dropped the first two but evened the series at two games apiece once things shifted back to Toronto. But enough was enough and James took the Cavs up a notch, winning Game 5 116-78 and Game 6 113-87.

“I remember going against [Michael] Jordan in 1996. He has that same type of mindset, that razor-like focus that you’ve got to fight against and you’ve got to overcome,” Casey said after their elimination.

The problem for the Raptors is they never overcame James and the Cavs. Impressive regular seasons in 2016-17 and 2017-18 were erased in a heartbeat after LeBron swept the Raptors in consecutive years. Dating back to May of 2016, Cleveland had won 10 consecutive playoff games over Toronto. Or as some said, LeBronto. Something had to change. And something definitely changed.

 

 

Reaching new heights

2018-Present

That takes us all the way to last summer. For too long the Raptors had gone far, but not far enough. It wasn’t enough that Casey was fired and replaced with assistant coach Nick Nurse. It wasn’t enough that LeBron signed out-of-conference with the Los Angeles Lakers.

Kawhi Leonard’s arrival sparked a new era for the Raptors, one that was meant to push the franchise to places they’ve never been before.

But that was all in danger of falling apart in the second round once again as the Raptors and 76ers battled in a closely contested Game 7. After Jimmy Butler tied the game with 4.2 seconds left to play, the stage was set for Leonard to show why the Raptors went out and got him.

It was eerily familiar to Carter’s shot 18 years earlier against the 76ers. From there, we all know the story.

“It’s a hell of a story. Obviously, what this franchise has been through its inceptions, what this city has been through in terms of its basketball growth, it’s a heck of a story to be going to the Finals and have a chance to win it all.” Fred VanVleet said after their series-clinching win over the Bucks on Saturday.

 

But, as VanVleet said, that story isn’t finished yet. Standing in Toronto’s way is a villain dynasty that’s won three of the last four titles and has dominated the league in ways never seen before. It won’t be easy, but a path to the Finals rarely is.

If the franchise can overcome as much as they already have, why can’t they overcome the Golden State Warriors?

“They’re the champions,” Leonard said Saturday. “We’ve got to go in, have the mental focus, enjoy the moment and take the challenge.”

Yes, it will be a challenge, but Raptors fans will certainly be enjoying the moment.