The list of egregious moves the Toronto Raptors made in the Vince Carter tenure:
1) Acquiring Kenny Anderson (who wouldn’t report), then trading him five days later for Chauncey Billups, then flipping Billups for Zeljko Rebraca, Micheal Williams, and a first-round pick (eventually Morris Peterson) a year later. Billups flourished in Denver and became a Finals MVP with the Detroit Pistons. Anderson, on the other hand, is another name in a handful of players who either refused to report or demanded to leave Toronto (Damon Stoudamire, Vince, T-Mac, Alonzo Mourning are other notable examples). At some point, it’s no longer a coincidence.
2) Signing Antonio Davis for 5 years-$63 million, Alvin Williams for 5 years-$28.3 million, and Jerome Williams for 7 years-$40.8 million — in the same offseason in 2001. To be fair, the Raptors later dealt Davis and J. Williams for Jalen Rose and Donyell Marshall — one of the few deals that the Raptors actually won, though they did pay an aging Jalen Rose 43.5 million dollars for one good season in three years.
3) Not signing a single free agent of consequence before or after that 2001 offseason — but how could they? Here’s the list of signees from 2001-2004: Jelani McCoy, Carlos Arroyo, Jermaine Jackson, Derrick Dial, Nate Huffman, Voshon Leonard, Greg Foster, Damone Brown, Art Long, Maceo Boston, Jerome Moiso, Milt Palacio, Mengke Bateer, Rick Brunson, Jannero Pargo, Dion Glover, Rod Strickland, Corie Blount, Rafer Alston (again), Loren Woods. Most of them played under 20 games in Toronto, and only four of them even played in two seasons – Palacio (139 games), Alston (137 games), Woods (72), and Moiso (43).
4) Trading Marcus Camby, fresh off leading the league in blocks per game at 23, for 35-year-old Charles Oakley. Oakley signed in Toronto for $18 million, then played three unremarkable (okay, bad) years before getting traded in 2001 with a 2nd-rounder for Brian Skinner, who never suited up. Camby, still active, developed into one of the better rebounding/shotblocking/defensive centers of this era.
5) Turning Doug Christie into the worst 42 games of Corliss Williamson’s career, then trading Williamson, two nobodies, and the first-rounder they got in the T-Mac sign-and-trade for Eric Montross and Jerome Williams. Christie played an integral part in Sacramento’s playoff runs from 2000-2004, Williams signed that 7-year contract and played decently off the bench for a couple of seasons, and Montross played himself out of the league by 2002.
6) Drafting Aleksander Radojevic 12th overall in the 1999 draft, Michael Bradley 17th in 2001, Kareem Rush 20th in 2002, and Rafael Araujo 8th in 2004. Some of the players drafted shortly after these four: Corey Maggette, Ron Artest, James Posey, Jason Collins, Zach Randolph, Brendan Haywood, Tayshaun Prince, Nenad Krstic, John Salmons, Andre Iguodala, Al Jefferson. The only draft hits in the VC era were Morris Peterson (a rotation player at #21 in the weakest draft in NBA history), and Chris Bosh (a no-brainer).
7) Signing Michael Stewart, a 6-10 center that shot 41.5% from the field (his best mark in Toronto), to a 6-year contract worth $24 million in 1999. After totaling 198 fouls to 174 points in four seasons, the Raptors traded him with a draft pick (eventually Jared Dudley) for Lamond Murray, who played 95 unremarkable games in three years. Total cost to the Raptors between these two: over $30 million.
8) Signing a 38-year-old Hakeem Olajuwon to a three-year contract, presuming that Olajuwon would be worth 6.3 million dollars as a 41-year-old. Olajuwon suffered foot, toe, thigh, and back injuries, “unofficially” retired at the end of the first season, and continued to take his paychecks throughout his contract. Total cost: $17.4 million.
(A final bit of irony: the Rockets retired Hakeem’s jersey on November 9, 2002… while playing the Raptors.)