The concern is both general and specific, and like most questions of great magnitude that contain various variables, is unanswerable without proper context.
Before offering a knowledgeable opinion worth more than two cents, first it has to be revealed what in fact the Celtics would be receiving in return for one of the five best players in their illustrious franchise's history.
If a guaranteed lottery pick in the 2014 draft is on the table, then the answer is an emphatic yes—with Danny Ainge privately popping a bottle of champagne in his office as soon as all the paperwork's ink is dry.
If it's for a prospect who boasts All-Star potential should everything fall into place, a deal will get done, and Pierce should pack his bags.
But these scenarios range from unlikely to "impossible without excessive blackmail."
If you haven't been paying attention these past couple years—or don't understand how the new CBA works—here's a quick primer: money is tight. Players in their mid-30s not named Tim Duncan are no longer worth eight figure contracts. Players in their early 20s who earn rookie scale money are of the utmost importance, and hold the highest value. By far.
Pierce will be 36 years old next season, entering the 16th year of his Hall of Fame career.
He can still make jumpers and pull-up threes, get to the rim, create his own shot in modest dosages and defend within a five-man scheme as well as anybody at his position. But his days of being the best, or possibly even second-best, offensive player on a championship contender are over.
Pierce is coming off a season in which he averaged the fewest minutes per game of his career (33.4), and, just as telling, a six-game playoff stint that produced an atrocious 10.7 PER. His trade value isn't what you'd call "good."
An example: if Ainge dangled Pierce in an effort to pry Harrison Barnes from the Golden State Warriors, they'd laugh very, very hard before hanging up the phone. Pierce will almost definitely have a better 2014 than Barnes on the court, but for a multitude of reasons, the days of trades like this happening—and GM's keeping their jobs afterward—are over.
And we haven't even begun to talk about the money. If the Celtics don't move or waive Pierce after June 30, he stands to make $15.3 million. Before June 30 they have the option of waiving him for $5 million. It's for sure a lot of money, and far more than Pierce is worth at this stage in his career, but any trade involving logic would bring back similar salary and keep Boston's short-term cap situation either the same or worse.
Trading Pierce would also result in an extremely displeased Kevin Garnett, and that's something the Celtics don't want unless they're interested in starting all over as soon as possible.
But even without Garnett and Pierce, Boston still has enough talent on its roster to avoid the lottery, especially in an Eastern Conference that should be grotesque for the second straight year (though the addition of Derrick Rose, and question marks such as Andrew Bynum and Rudy Gay could make things interesting).
Rajon Rondo is a four-time All-Star and the best passer in basketball, and he'll be surrounded by talented, young pieces like Jeff Green, Avery Bradley and Jared Sullinger (not to mention a motivated Jason Terry, and a Courtney Lee who couldn't possibly be any worse than he was in his debut Celtics season, plus whatever Boston would get back in return for Pierce).
If they move Pierce for young salary filler then the organization will not only take an awkward step sideways, but they'll be upsetting a fan base and a city that worships him like few other cities worship their favorite professional athlete.
It all depends on what they get back, of course, but treating the situation with realistic eyes, and going off what NBA teams are placing more value on now than ever before (draft picks and rookie contracts) then it might make the most sense to keep Pierce (and Garnett), go through one more season with the gang all together, then let things run out on their own course.