The move comes as a surprise after the club recently acquired point guard Kyle Lowry for Gary Forbes and a future first-round pick.
As reported by The Globe and Mail, recent rumors swirled that the Raptors would try to trade point guard Jose Calderon, or amnesty his contract, thus making him an unrestricted free agent.
However, it looks like the Raptors are setting Bayless free instead.
From the outsider looking in, you would question why the Raptors would elect to keep an expiring Jose Calderon over the younger, more long-term option in Bayless.
The Raptors as an organization enjoyed their most successful season when they won the Atlantic Division working with the point guard tandem of TJ Ford and Calderon.
The addition of Lowry, who comes in as a much better shooter, and defender than Ford, gives the Raptors a new element at the point guard position.
Couple his skills with Calderon's innate ability to run and offence and be productive with the ball, and you have the makings for one of the best, if not the best point guard tandem in the NBA.
General manager Bryan Colangelo will be looking to trade Calderon by the trade deadline if not sooner. Having a backup point guard making the most money on the team seems like a bit of a waste of cap space if you ask me.
Here is a list of six point guards that could replace Bayless' spot on the Raptors roster.
Like I said, Jose's game has always been best when coming off the bench. Calderon is getting older, slower, and more injury prone as he's been aging. Having him play more manageable minutes could prolong his season, and the Raptors will be reaping the benefits as they hope to repeat their Atlantic Division winning season in 2006-07 when Calderon last played backup point guard for the club.
A very good defender, and a decent distributor, Hinrich remains a free agent looking for work. Hinrich has the ability to guard both the 1 and 2, and has come off the bench for the Hawks. His veteran leadership off the bench would help the Raptors out immensely. However, injury concerns could outweigh the benefits of adding Hinrich to the team.
Likely could only be added if the Raptors amnesty Calderon and sign him to a larger deal. Right now, Sessions is arguably the best available point guard option in the free-agent market. Look for a team like the Heat, Mavericks or Bulls to add Sessions, but don't count out the Raptors from putting in a last-minute offer.
More of a scoring combo guard, Sweet Lou Williams would be the Raptors' newest version of the Brazilian Blur Leandro Barbosa. Williams has better point guard skills over Barbosa, but their main objective as a player is to score in bunches. The Raptors would likely need to amnesty Calderon or making a sign-and-trade and acquire Williams.
Probably the largest wild card of the bunch. Flynn was highly sought after by the Raptors in the DeMar DeRozan draft, eventually going to the Minnesota Timberwolves sixth overall. The Raptors picked ninth and chose DeRozan.
Flynn when given playing time last season played amazingly well averaging nearly 18 points a game and seven assists per game in the last five games of the season for the Trail Blazers. Flynn would come at a cheaper price, and likely come to Toronto on a small contract.
Say what? Yes, the Raptors declined the qualifying offer to Bayless, but in the end it doesn't mean he can't come back to Toronto.
By renouncing Bayless' bird rights and pulling the qualifying offer off the table, the Raptors gained a bit more financial flexibility and still left their options open for Bayless.
Bayless can still be re-signed by Toronto, who would be over the salary cap, or he could also be included in a sign-and-trade.
With point guards Kyle Lowry and Jose Calderon manning the point, DeRozan and rookie Terrence Ross manning the shooting guard position, and recently signed Landry Fields possibly in the mix too, Bayless' time in Toronto could be coming to an end.
But don't count out the Raptors amnestying Calderon and possibly going after a big man, or a small forward to round out the roster.
Are the Raptors a playoff contender? Hard to say, but at least they are moving in the right direction.