I've spent entirely too much time thinking about this subject so I'm going to go ahead and actually write something about it! If the Raptors think they have a chance to beat the Cavs in the Eastern Conference finals they probably will need an upgrade at the 3/4 to do so. This trade would also help them avoid yet another embarrassing first round playoff loss at the very least. With Kyrie seemingly playing better heading into the All-Star break perhaps our chances in an eventual series against the Cavs would not be as good as they appeared when he was really struggling in his return from his knee injury, but a healthy Demarre Carroll could really take this team to another level, and another similar player to help him guard the Lebron/Love pick and roll could perhaps be enough to make it a fair fight. I think that's the player the Raps want, so I will be focusing more on 3-and-D forwards who can guard both the 3 and 4. A true PF with less versatility defensively is still possible, as are certain offense-first wing players, and I'll try to consider all the potential options.
Ideal World But (Probably) Not Gonna Happen:
Al Horford (Hawks): Horford is a stud on both ends of the floor and would give the Raps everything they desire in a power forward, aside from elite 3-point shooting. I don't really think the Hawks are as eager to move him as the rumour mill wants you to believe though. His contract is expiring sure, but Atlanta will likely want to keep him and hold the trump card in resigning him unless a team is willing to drastically overpay, which Masai is too smart to do.
Danilo Gallinari (Nuggets): Perhaps not quite the defensive stopper they desire but the substantial upgrade on offense and having him for at least one extra year would be fantastic. This is also why he's going to cost too much since teams still overpay for offense, and I don't think Denver especially wants to move him. The player option in his contract for a 3rd year could really hurt if he gets injured again.
You Could Get Him, But Do You Really Want Him?:
Thaddeus Young (Nets): Thad is a pretty good basketball player but I don't see him as the fit the Raps want. He's not good enough defensively and while he'd be a nice boost to the offense his mediocre 3-point shooting doesn't really fit what the Raps seem to prefer doing on offense. Maybe if the price gets low enough.
Ryan Anderson (Pelicans): An elite offensive option but liability on defense, and on an expiring contract. I don't think the price is going to be right here, and I'm not sure he's as big an upgrade as people want to believe. If the price came down I'd take him over Thad.
Probably Not Available:
Jared Dudley (Wizards): It seems that Washington are set on trying to make a run at the playoffs to help their case in the Kevin Durant sweepstakes. If they are willing to move Dudley and his expiring deal he is exactly the type of under appreciated player the Raps might be able to get on the cheap to provide decent defense and elite 3 point shooting. He has already spent much of the season playing the stretch 4 for the injury plagued Wiz.
Omri Casspi (Kings): Who knows what the Kings are liable to do, his 3 point shooting could help and while the Kings are a train wreck on D it doesn't seem to be his fault. Could be a solid cheap addition.
Interesting But They Don't Help Right Now:
Terrence Jones (Rockets)/Markieff Morris (Suns): Both young PFs who show potential and are interesting buy low candidates. Neither is ready to step in and help a serious playoff team right now though and both have the issue of being inconsistent at best defensively. I'd probably rather gamble on Pat Pat going forward and he's the better fit right now too.
The Obvious Fit:
PJ Tucker (Suns): There have been plenty of rumours about the Raps being interested in Tucker and for good reason; he ticks a lot of boxes. A plus defender who could switch onto stretch 4s, he and Demarre Carroll would be an ideal combination to defend Lebron and Love. He's on a cheap contract that appears to have a team option for one more year, which would bring him back for the final year of Lowry's current contract next year as well. Compared to the current option for that role in James Johnson, Tucker gives you serviceable 3-point shooting: good enough that he must be guarded on the perimeter, which prevents him from being a negative on offense. As a defense first type we can perhaps be more optimistic that the price for Tucker would be right, but one wonders if the Suns would insist on moving Markieff Morris in a trade with Tucker, which could make things more difficult. Ultimately, I still think Tucker is the most likely of these players to be a Raptor by tomorrow evening.
The Raptors have the assets to land any of these players. However, in a year where even if you happen to sneak past the Cavs you will have to face an all-time great team in the finals, it doesn't make sense to pay too high a price. Here's hoping Masai finds the right move for now, while keeping the future bright.