The Boston Celtics shouldn't overthink Jaylen Brown's possible supermax contract extension this offseason.

They should hand over the large sum of money he is eligible for and put it in any bag, backpack or suitcase that Brown desires. And the Celtics should have no regrets about doing so.

Brown can get a five-year, $295 million extension after the 26-year-old garnered Second Team All-NBA honors this past season, averaging a career-high 26.6 points per game on 49.1% shooting from the field. He also totaled 6.9 rebounds and 3.5 assists per game.

Giving Brown the supermax contract, especially with star running mate Jayson Tatum in line for one next offseason, is a massive investment and one that certainly comes with questions no matter how well the two-time All-Star has progressed and performed over his seven-year career.

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The Celtics have had plenty of success with Brown on board, but winning the NBA title has eluded them. Brown shoulders some of the blame for the Celtics continually coming up short, including this postseason, which is why some would be hesitant to extend him or not extend him at all. But his postseason track record in totality shows he can be the No. 2 player on a championship team.

Just last year in the NBA Finals, Brown was praised for having a better series against the Golden State Warriors than Tatum. In the brightest of lights that the league has to offer, Brown didn't shrink like Tatum did and showed the mettle necessary to win at that level. When the Warriors closed out the Celtics on their home court, it was Brown who netted 34 points trying to keep Boston's season alive while Tatum put up 13.

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But Brown's solid postseasons -- he's averaged over 20 points per game in each of the last three playoff runs by the Celtics -- and showing in the Finals has been overshadowed by the bad taste in everyone's mouth left by his final performance this season. With Tatum suffering an ankle injury just minutes into Game 7 of the Eastern Conference finals against the Miami Heat, it was on Brown to step up and he stumbled. Brown turned the ball over eight times, which was the same number of shots he made, as the Celtics were embarrassed once again on their home floor.

The turnovers are a massive issue for Brown. While the turnovers have persistently existed for him, it is a correctable problem. And if he can fix his ballhandling and become more of a playmaker -- something Ime Udoka wanted out of both Brown and Tatum when he took over -- he'll be an even bigger asset for the Celtics capable of leading them to a title.

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The other big mark against Brown is that some believe he and Tatum can never truly co-exist together. Their skill sets are too similar and Brown wants to be in the leading role and have his own team, something that will never happen in Boston with Tatum there.

But this is where the Celtics should put their trust in both Brown and Tatum that they will figure things out. Even though he never publicly admitted it, Brown certainly wanted personal success to get to supermax land. It's tough to blame him, though, given the dollar figures at stake. But all Brown has ever talked about out in the open is winning a championship and he's displayed the demeanor and toughness needed to get there. The same can't be said about Tatum, yet.

The Celtics just need to realize what they have in Brown and Tatum. Two of the top players in the league who are both entering the prime of their careers. There's no reason whatsoever to want to move on from that. Two star wing players still in their mid-20s don't grow on trees in the NBA and teams around the league would love to be in Boston's position.

Brown and Tatum aren't without their faults, but given their supreme talent, they should be able to overcome it. And the Celtics should ride it out.

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When teams can hand out extensions to eligible players starting Saturday, the Celtics should waste no time cutting the massive check for Brown and put the ball in his court to accept.

Having Brown and Tatum together is still the best route for the Celtics to get back to the Finals.

Featured image via Sam Navarro/USA TODAY Sports Images