The Celtics like Bradley: He's 23 years old, one of the best defenders in the league and coming off a year in which he made very promising and impressive strides with the ball.
Ideally, though, the team can't afford to give anybody a contract that outweighs their production. If Boston adds a new long-term deal to the books this summer, it better be someone they think can contribute to a contender.
Most importantly for Bradley, he seems to be a suitable fit with Boston's best player: Rajon Rondo.
The ability to knock down an open three—or better yet, make the defense worry that looming threes are a potential threat—is a key trait any backcourt partner must have beside Rondo. Bradley shot nearly 40 percent from beyond the arc last season.
Rondo, Boston's All-Star point guard, shot 44.4 percent from the floor with Bradley on the court last year and 38.6 percent with Bradley on the bench.
Offense is an area Bradley can definitely stand to improve, but it's on defense where he's a natural fit for any point guard, especially one who carries such heavy responsibility with the ball.
With Bradley on the court, Rondo doesn't need to worry about defending the opposing point guard—a harder job than it sounds—nor does he need to worry about fighting over or under on-ball screens or trying to contain some of the league's fastest players off the dribble.
Bradley can handle all of that, doing an even better job on the perimeter than Rondo, who is a four-time All-Defensive Team member.
Bradley can hold his own and figures only to get better. But the prism through which he's viewed will be altered dramatically if another team extends him a hefty offer sheet this summer.
On a rookie-scale contract, Bradley's value is obviously high—two years ago he supplanted Ray Allen in the starting lineup on a championship contender. But if Bradley's looking for $8 million per year (which isn't even above market value for a shooting guard his age), the Celtics may decide to fill their backcourt elsewhere.
Working the trade market isn't the best option for Boston—the team isn't playing meaningful basketball right now. They aren't contending for a title, so sacrificing future assets (i.e. draft picks) in a separate deal is the last thing they want to do. They'd be better off just signing Bradley outright.
Free agency is the next logical option, but two things are holding them back.
The first is cap space. If the Celtics don't sign Bradley and waive Keith Bogans, they'll be roughly $15 million under next year's salary cap. They'd still need to fill six roster spots, and that figure is calculated before factoring in the team's two first-round draft picks.
Their situation isn't exactly flexible.
The second issue with free agency here is options. The market for worthwhile shooting guards is bone dry. There might be one or two value plays the Celtics could make, but other teams will be targeting the same guys, and none are better than Bradley anyway.
Someone along the lines of elite three-point shooting journeyman Anthony Morrow is Boston's best bet. He'd be a great fit beside Rondo, but shooting is about all he's good for, and it's tough to argue that he's worthy of a long-term investment.
This brings us to the draft—the only option where replacing Bradley makes some sort of sense, be it with pick No. 6 (Marcus Smart, Dante Exum) or No. 17 (Gary Harris, Nik Stauskas, Zach LaVine).
Nearly all these players have already worked out with the Celtics. Here's what they're capable of bringing to the table, courtesy of CelticsBlog's Kevin O'Connor:
Gary Harris and Nik Stauskas are two intriguing options if the Celtics end up trading down from #6 or up from #17. Harris is a defender that will rip your heart out with his absolutely tenacious style. He would fit right in, though he could also play some point guard as a complimentary offensive player.
Stauskas is really on the opposite end of the spectrum as he is a poor defender but a terrific offensive player. The Michigan combo guard has arguably the best shot out of anyone in the draft and can hit from anywhere on the court. If the Celtics selected him, Brad Stevens would have a guy he can runs play for immediately.
And lastly, Marcus Smart is the top-ranked player as part of the group workout. Most know the deal about him at this point since he is discussed so much, but his greatest traits are no doubt his doggedness and his will to win. Smart is a bulldog on defense and can defend two, possibly three positions. He is laterally quick enough to stay with speedy guards, but he's strong enough to handle wings.
In the end, the market will decide whether Bradley stays with the Celtics. The team has plenty of reasons to keep him on board, even if they draft someone like Smart, who could very well be the better player his first day in the league.
But the options to get better beyond that are slim or nonexistent. If another team gives Bradley an outlandish price tag, the Celtics will be more than ready to let him walk. If not, they'll be content keeping him on board another four years.