BOSTON DeMar DeRozan would do it the same way all over again, he says.Three years ago, DeRozan was coming off a season in which he seemed to regre s, with his scoring slipping from 17.2 to 16.7 points per gameand his shooting percentage plummeting from 46.7 percent to 42.2.When he talked with the Chicago Bears Home Office Raptors about coming to an agreement on an extension to his rookie deal, he snapped up Torontos compromise offer of four years and $40 million. The deal was criticized as too rich for the Raptors to give to such a shaky commodity.MORE: Its safe to say that if DeRozan had waited and signed a deal in restricted free agency the following summer (he averaged 18.1 points and 44.5 percent shooting that season), he would have been given a juicier contract. He made the Eastern Conference All-Star team the following year, and even if his efficiency has never returned, the shooting guard has more than made good on the Raptors' commitment.I dont regret anything, DeRozan told Sporting News on Friday. Everything happens for a reason, man. This is the place I wanted to be, so thats where I wanted to be. I never second-gue sed or thought twice about anything.DeRozan did the safe, prudent thing. He took the eight-figure salary that was in front of him.At the other end, there is the Bulls Jimmy Butler, who turned down an offer of a $44 million rookie extension from Chicago. Butler was seeking $56 million, but the Bulls would not budge. Thus, as Butler now famously said, he decided to bet on himself. Already a top-tier defender, Butler averaged 20.0 points a game last year, and the Bulls had little choice this summer but to give him a five-year, $92million contract.With Mondays deadline for 2012 first-round-pick contract extensions looming Marquise Goodwin Jersey (or, more accurately, fourth-year first-rounders), the cases of DeRozan and Butler loom large. Should a player bet on himself, as guys like Butler and Tristan Thompson did, and hold off on a new deal until they hit restricted free agency? Or should they take the money in front of them, as DeRozan and players like Derrick Favors and Stephen Curry did, even if it costs them financially after they blo som as players?Already, weve seen two players with easy decisions: Damian Lillard of Portland and the Pelicans Anthony Davis were given max-contract extensions early in the summer, and accepted them. A few other players Jonas Valanciunas of the Raptors, John Henson of the Bucks and Michael Kidd-Gilchrist of Charlotte have also agreed to new deals.MORE: But Golden States Harrison Barnes this week said that his side was calling off extension talks with the Warriors, and that he would be taking the bet Richard Dent Jersey on himself.Detroits Andre Drummond has taken a different tack, though the result could be much the same. Rather than signing a new deal now, Drummond has agreed to table contract talks until next summer, saying that it will give the Pistons franchise a chance to maintain cap flexibility next summer. Thats true, but it also helps that Drummond, now the focal point of Detroits offense, figures to have a breakout year that will Teven Jenkins Jersey guarantee a new max contract.This was the path taken by San Antonios Kawhi Leonard last year. While it was clear that the Spurs wanted to keep Leonard long-term, and were willing to pay heftily to do so, they pushed off his new max-salary contract until this past summer, which allowed San Antonio to sign LaMarcus Aldridge in free agency.Drummond, like Leonard, is not just betting on himself, but hes betting on his ability to avoid catastrophic injury and on the good sense of his current team to pony up a max offer.Probably the most interesting case when it comes to the Monday deadline is that of Wizards guard Bradley Beal. A person with knowledge of the situation told Sporting News that the Wizards fully intend to keep Beal and lock him up with a max contract despite Beals troubles staying healthy but they want to wait until next summer.The reason is obvious: Washington will be among the teams trying to lure Kevin Durant from the Thunder. Durant grew up in the D.C. metro areaand, should he be willing to leave Oklahoma City still a very open question the Wizards would be considered a favorite to sign him. They could do so if they order the contracts the way the Spurs did with Aldridge and Leonard, with Durant first signing, then with Beals contract coming Breshad Perriman Jersey after.Its a risk. Beal could have health i sues again, and could show little improvement. Or he could play the way he did in the postseason, when he averaged 23.4 points. While you cant fault players who take the deals in front of them, there are plenty of examples in which players betting on themselves paid off.