The what-ifs of draft picks are incredibly easy to contemplate successfully, so while we could debate what could have happened to the Chris Bosh-era Raptors if they had picked Andre Iguodala in 2004, or Brandon Roy in 2006, the below time-line examines the actual trade history from the 03-04 season until his departure in the summer of 2010.

03-04

• Jalen Rose, Donyell Marshall and Lonny Baxter from Chicago for Antonio Davis, Jerome Williams and Chris Jefferies.

• Roger Mason from Chicago for Rick Brunson.

• Robert Archibald from Orlando for Banteer Mengke.

Breakdown: The Raptors were thinking much more about Vince Carter at this point than they were about Chris Bosh and this trade was intended to give the team more offense, even if it ended up putting more pressure on Bosh in the frontcourt.

04-05

• Vince Carter to New Jersey for Alonzo Mourning, Aaron Williams, Eric Williams and two first round picks. The first pick became Joey Graham and the second pick was used for cap relief from Jalen Rose.

Breakdown: Carter was still only 27 at the time and not eligible to be a free agent for several more seasons. This is essentially the same situation Denver finds themselves in with Carmelo Anthony, except Anthony is quickly approaching free agent and hasn't given up trying the way Carter did. The reaction of Jalen Rose where he asked if they acquired Richard Jefferson still sums up the trade appropriately. The Nets and Magic each arguably received more in return when they traded him over the past few months.

New Jersey didn't have anything else in the way of young talent to offer Toronto, but it is hard not to imagine this trade being improved upon by a rival team closer to the deadline, or merely wait it out until the summer.

05-06

• Mike James from Houston for Rafer Alston.

• Aaron Williams to Hornets for second round picks in 2006 and 2009. The first pick, Edin Bavcic, was the 56th overall selection and sold to Philadelphia. The 2009 pick was used in the upcoming Rasho Nesterovic trade with San Antonio.

• Jalen Rose and the 2006 first round pick from New Jersey sent to New York for Antonio Davis.

• Nesterovic acquired from San Antonio for Matt Bonner, Eric Williams and New Orleans' 2009 second rounder.

• Kris Humpries and Robert Whaley acquired from Utah for Rafael Araujo.

• Charlie Villanueva sent to Milwaukee for T.J. Ford.

Breakdown: All of the moves made in 05-06 when Bryan Colangelo assumed GM duties were prudent and created an improved situation where the Raptors could go onto to win the Atlantic Division in 2007. Their benefit ended up being largely short term, though they wouldn't have been in a better position if they were to be undone.

This is where exchanging Andrea Bargnani for Brandon Roy could have changed the franchise since the Raptors won 47 games in the following season.

Colangelo sold high on Villanueva's rookie season, knowing the overlap with Bosh would always be too significant and the need for improved point guard play coming out of the 05-06 season was even more significant.

06-07

• Juan Dixon acquired from Portland for Fred Jones.

• Carlos Delfino acquired from Detroit for second round picks in 2009 and 2011.

Breakdown: Colangelo did his work for 06-07 in the offseason and let his team stay in tact in a down year for the Atlantic Division.

07-08

• Primoz Brezec acquired from Detroit for Juan Dixon.

Breakdown: Nothing major for the Raptors, who took a step backwards and barely made the 2008 Playoffs.

08-09

• Jermaine O'Neal and Nathan Jawai acquired for T.J. Ford, Rasho Nesterovic, Maceo Baston.

• Hassan Adams sent to Clippers for conditional second round pick and cash.

• Jermaine O'Neal and Jamario Moon sent to Miami for Shawn Marion and Marcus Banks.

• Jason Kapono sent to Philadelphia for Reggie Evans.

Breakdown: O'Neal was a bold move to give Bosh more help in the frontcourt, but he quickly aged and they quickly and wisely cashed out on him with the Heat trade.

09-10

• Hedo Turkoglu, Antoine Wright and Devean George acquired in multi-team trade that sent Shawn Marion, Kris Humphries and Nathan Jawai to Dallas.

• Marco Belinelli acquired from Golden State for Devean George.

• Amir Johnson and Sonny Weems acquired from Milwaukee for Carlos Delfino and Roko Ukic.

Breakdown: The Raptors had to do something quickly to give Bosh hope and the acquisitions were just about as good as possible. Turkoglu could have been used more effectively but basically was a no-show, while the Jarrett Jack signing, along with the moves for Belinelli, Weems and Johnson were all ones where you have to give them a win.

Bosh's wheels to Miami were already in motion and nothing short of DeMar DeRozan instantly being Air Canada II was either going to turn the Raptors into a title contender and/or make him want to stay.

• Click here to browse Toronto's transaction history in full.