Whether you obsessively follow the Toronto Raptors or recently got on the bandwagon, every fan knows that Kawhi Leonard's pending free agency is the biggest question facing the organization. Leonard, the two-time NBA Finals MVP and winner of Defensive Player of the Year in 2014-15 and 2015-16, will surely opt out of the final year of his contract in order to sign a max deal. While only Leonard and those close to him have any idea what he may do come the 30th of June and beyond, most have speculated that his decision will come down to two teams - the Toronto Raptors and the Los Angeles Clippers - with some teams possibly getting meetings or calls (New York Knicks, Brooklyn Nets, Los Angeles Clippers).
This post focuses on just Toronto and the LA Clippers, rehashing some of the general points spoken and written by the talking heads as well as going into more depth on the key issues. I've organized the post by issues instead of laying out all the positives and negatives for each team. This approach allows for a better comparison between the two teams.
Note: this is a very long and detailed read.
Los Angeles Clippers – The Clippers have one of the best front offices in the game, led by former New Jersey Nets head coach Lawrence Frank, who holds the title of President of Basketball Operations; General Manager Michael Winger; and head coach Doc Rivers. At this year's trade deadline, Frank and Winger traded pending FA Tobias Harris along with Boban Marjanovic and Mike Scott to Philadelphia for Wilson Chandler, Mike Muscala, Landry Shamet, Philadelphia's protected 2020 first-round pick, Miami's unprotected 2021 first-round pick, and Detroit's 2021 and 2023 second-round picks. The massive haul showcased the front office's willingness to make shrewd moves in order to create a sustainable winner in Los Angeles.
Despite the trade and with the Clippers holding on to the 8th playoff spot, the team went on a roll. They easily won the 8th playoff spot (although they could have easily been as high as 6th in the competitive Western Conference) with a roster devoid of any superstars or even All-Stars. The Clippers were extremely competitive in every game, which is a testament to the Rivers' coaching job this past season. He took a team full of young players and cast-offs and made them winners, and this collection created problems for eventual Western Conference champions Golden State Warriors in the playoffs as they extended their series to six games.
Aiding the front office's job is owner Steve Ballmer, whose net worth is estimated at US$49.1 billion. Ballmer has given management all the resources and tools it requires to build a winner while staying out of the day-to-day operations. Ballmer has already committed to pay the tax if it means luring big free agents to the Clippers.
Toronto Raptors – The Toronto Raptors may have the best front office in all of basketball, led by the charismatic and visionary Masai Ujiri and his lieutenants – GM Bobby Webster, Senior Advisor Wayne Embry, Assistant GM Dan Tolzman (who is a future GM candidate), and VP of Basketball Operations and Player Development Teresa Resch. This group has not only made some bold trades (DeRozan for Leonard; Gasol for three players and a draft pick), but they have unearthed gems in the draft and free agency, namely Pascal Siakam, Fred VanVleet, and Norman Powell. The group’s ability to think long-term and strategically, which includes a commitment to player development, is what sets it apart from most front offices.
Another example of Ujiri’s out-of-the-box thinking was the hiring of Nick Nurse as the franchise’s ninth head coach in its history. Nurse’s calm demeanour, affable personality, and willingness to experiment and think way beyond the parameters of tradition has shot him into the upper tiers of NBA head coaches. With sixteen playoff victories, he’s already has the second most post-season wins of any Raptor head coach (Dwane Casey has 21).
The Raptors’ ownership group is a bit unconventional by NBA standards. Instead of a flamboyant or opinionated individual owner, Maple Leaf Sports and Entertainment allow their sports management groups to run all their teams. They instead focus on the day-to-day business operations and operate like a Fortune 500 company. With their tremendous wealth, MLSE has provided Ujiri and his staff with the resources to make the Raptors not only a successful and winning franchise but a destination for players to want to play.
The big question hovering over Toronto is Ujiri’s future. During the NBA Final and immediately after its conclusion, reports were released that the Washington Wizards’ owner Ted Leonsis, who also owns the Washington Capitals and is the majority owner and CEO of Monumental Sports, would offer Ujiri a US$10M+ annual salary, an ownership stake in Monumental Sports, and a position to oversee both basketball and business operations. Another report later stated that Leonsis would not be approaching Ujiri anytime soon, but the threat of a substantial offer remains a lingering cloud over the Raptors and, thus, may affect Leonard’s decision.
Los Angeles Clippers – The Clippers only have 8 guys signed for the 2019-20 season with veterans like Patrick Beverley, Michael Beasley, Garrett Temple, and JaMychal Green headed for free agency. None of these players, however, are considered critical to the team’s immediate and long-term future.
Their current main core compromises of very promising young players and veterans. Point guard Shai Gilgeous-Alexander headlines the youth on the team, and the 20-year old (21 in July) Canadian played with tremendous poise in his rookie season. He’s already a solid defensive player, and his offence was way better than anyone anticipated. Jerome Robinson, the Clippers’ other first-round pick from the 2018 Draft, has the potential to be a long-range threat at SG while the aforementioned Shamet could develop into a defensive stopper. Both have starting potential, but they need to be more consistent. This off-season is key for both since they are on the older side of being considered prospects (both are 22 and turn 23 during the season).
In Danilo Gallinari, Lou Williams, and Montrezl Harrell, the Clippers have a solid group of veterans. The latter two lead arguably the league’s best bench.
Toronto Raptors – Toronto will return their NBA championship roster largely intact with Leonard and Danny Green being the only major contributors headed to free agency (I’m assuming Marc Gasol will pick up his $25.5957M option).
Like the Clippers, the Raptors have a great mix of veterans and young talent. Unlike LAC, however, Toronto has All-Stars on its roster (Kyle Lowry, Gasol) and a future All-Star and possibly superstar in the making (Siakam). In addition, the Raptors have more depth with former Sixth Man of the Year nominee Fred VanVleet, former NBA All-Defence selection Serge Ibaka, and talented youngsters in OG Anunoby and Norman Powell. Although Lowry and Gasol are ageing, a core of Leonard, Siakam, Anunoby, FVV, and Powell would still make the Raptors a playoff team.
Los Angeles Clippers – Prior to the playoff run, the big story around the Raptors was Leonard’s load management. The quiet yet intense small forward played in 60 games during the regular season, but he ended up playing in all of the Raptors’ 24 playoff games and led all players in minutes played. Can the Clippers replicate the load management scenario? Load management will likely be even a greater priority for Leonard following the devastating injuries to Kevin Durant and Klay Thompson plus Leonard stating that he was sore and aching after Game 6.
In Mark Simpson, who holds the title of Director of Performance, the Clippers have a disciple of Alex McKechnie, who holds the title of Director of Sports Science in Toronto. As such, the Clippers will likely use very similar techniques and applications when managing Leonard’s minutes and games played.
But can the Clippers afford to keep Leonard out for 22 or more games? Even with Golden State likely to, as Brian Windhorst said, “hit pause” on the upcoming season, other teams in the Western Conference will manoeuvre to be the new alpha dog. Staples Center co-residents the LA Lakers got a head start with the acquisition of Anthony Davis, and they will still have over $23M in cap space to spend in free agency. Other non-playoff teams like the Sacramento Kings and Dallas Mavericks are likely to make big jumps next year while the Minnesota Timberwolves and New Orleans Pelicans could surprise.
Toronto Raptors – Leonard and McKechnie have formed a strong bond, which the mercurial talent admitted in interviews at the end of the season. Following the Raptors’ defeat of the Milwaukee Bucks, the two can be seen fist-pumping one another to acknowledge the work they’ve done to ensure Leonard’s health in May and June.
Load management will no longer be a storyline in Toronto. Leonard could sit out half of next year’s games, and no one will complain as long as he’s ready for the post-season. In addition, the Raptors proved they could win without him, going 17-5 in the games he sat out. With expected improvement (and hopefully good health) from Anunoby plus further growth from VanVleet, Powell, and McCaw (whose jump shot went from unreliable to very dependable), the Raptors should continue to win games without Leonard. They cannot, however, win a championship without his presence.
Los Angeles Clippers – Everyone knows Leonard is from Southern California and recently purchased a $13M home in the San Diego area. Whether this is a factor or not is unknown, but if playing close to home is the deciding factor then Leonard will be signing with the Clippers and there’s nothing that Toronto can do much about.
Toronto Raptors – Toronto is in Canada. It gets cold in the winter. It’s a 5 1/2-hour flight from LA. It is one of the most cosmopolitan cities in the world. But it is quite far from home.
Los Angeles Clippers – Los Angeles is the second-largest market in North America. The marketing opportunities are enormous not to mention the chance to rub shoulders next to Hollywood’s biggest stars and music’s highest-grossing artists. But will there be enough sponsors for LA’s increasingly crowded sports scene?
With LeBron James on the Lakers and Anthony Davis joining him and Lakers still being considered the NBA’s marquee franchise, companies will most likely focus their attention on getting James, Davis, and whatever other FA they sign to endorse their products. The media’s attention will also be on the Lakers full-time. Although the Clippers will become relevant again with Leonard in the fold, he may not receive the sponsorships and attention he deserves (and reportedly quietly craves according to reports prior to his trade from San Antonio). New Balance, though, will most likely want Leonard in LA, where they likely believe he can make a bigger impact on the global stage than Toronto.
Toronto Raptors – Toronto is the fourth-largest market in North America, nipping on the heels of Chicago and not far off LA. But it’s not just a city that adores Leonard, but an entire country of 37 million people. He is already a national hero, and the endorsement possibilities are endless.
Los Angeles Clippers – The Clippers are in great cap shape now and moving forward. They have enough cap space to sign one player to a max contract and a second player to a deal in the $20M-$22M range. If they can deal Gallinari, then they have two max-salary slots.
For the 2020-21 season, they only have $8M in commitments, although this doesn’t account for the option years on Gilgeous-Alexander’s, Robinson’s, and Shamet’s rookie contract. Even when factoring these players’ salaries, the Clippers will have close to $100M in cap space (less if they sign Leonard).
LA does not own a first-round pick this year. However, they do have all of their first-round picks from 2020 and beyond plus others. Here’s their first-round pick status:
2019 - To BOS (via MEM)
2020 - Own; PHL 15-30
2021 - Own; MIA (via PHX to PHL); PHL 15-30 if not already settled
2022 - Own; PHL 15-30 if not already settled
2023 - Own
2024 - Own
2025 - Own
Los Angeles, as such, can sell Leonard on the idea that the Clippers are well-positioned to create a sustainable winner. They may not win the NBA title next season, but beyond that they should be perennial contenders.
Toronto Raptors – Toronto is capped out for the upcoming season and will likely pay a hefty luxury tax bill in 2019-20 should they re-sign Leonard. Come 2020-21, though, the Raptors will likely have a lot of cap space. Currently, only Powell’s $10.865952M contract is on the books, although Anunoby’s $3.872215M option will get picked up and Siakam will likely be the recipient of a new max contract (likely to start around $28.5M depending on what the salary cap is). Even with these three players’ contracts and a re-signed Leonard, the Raptors should have enough cap space to sign another player to a max contract.
In terms of draft picks, the Raptors’ situation is as follows:
2019 - To SAN
2020 - Own
2021 - Own
2022 - Own
2023 - Own
2024 - Own
2025 - Own
Los Angeles Clippers – Bringing the Clippers their first NBA Championship. The possibility of giving two different franchises their first Larry O’Brien Trophy could highly appeal to Leonard. It would cement his status as a Hall of Famer and one of the game’s very best players. Should he be the MVP of the Finals, he would be the only player in the history of the NBA to accomplish these feats.
Toronto Raptors – The Drake factor – not just in terms of what Aubrey Drake Graham brings in terms of profile and publicity but that he has shown a person can be a global sensation while still calling Toronto home. Then there is the chance to repeat as NBA Champions, which Leonard has yet to experience.
BIG QUESTION MARKS
Los Angeles Clippers
- Can LA replicate Toronto’s load management approach and still be competitive, especially in an increasingly competitive Western Conference?
- How close are the Clippers to being legitimate contenders?
- Is Los Angeles the city, in general, and the Staples Center, specifically, big enough to support LeBron James, Anthony Davis, Kawhi Leonard, and whatever other FA the Lakers sign?
- Will Masai Ujiri stay or go?
- After the 2019-20 season, what will the Raptors look like and will they remain competitive?
- Will the weather and location ultimately be the overriding factors in Leonard’s decision?
Los Angeles Clippers – The maximum the Clippers can offer is four years, $140.6M.
Toronto Raptors – Toronto can offer Leonard as much as a five-year, $189.7M contract.