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The Boston Celtics went from competing in the Eastern Conference Finals to suffering a gentleman’s sweep in the first-round. Boston knows Jayson Tatum is on the path to superstardom, and Jaylen Brown might join him in a few years. However, the Celtics need to make significant offseason changes to stay relevant in the evolving Eastern Conference.

Boston is one of the NBA’s premier franchises, but it’s 13 years removed from its last championship run and has only hung one banner in the rafters since 1986. The Celtics are consistently competitive during the regular season, but they’ve lacked the depth and superstar leader to get over the hump recently.

Tatum is arguably Boston’s best player since Ray Allen, Kevin Garnett, and Paul Pierce patrolled the floor. The Celtics have their star locked up on a long-term deal. Recently promoted President of Basketball Operations, Brad Stevens must surround the 23-year-old with a championship-caliber roster.

Cap constraints and an improving conference could push Boston to the brink this offseason.

Finding a Head Coach

Stevens recently left his role as head coach to take over for Danny Ainge in the front office. Amidst the shake-up, Celtics governor Wyc Grousbec and Stevens vowed “to win Banner 18, or die trying.” It’s hard to match the intensity of basketball lifers in the NBA’s all-time winningest city, but that’s a challenge the next Celtics head coach must meet.

While several experienced coaches are interviewing for jobs, the first-time head coach market is incredibly strong. However, reports claim the Celtics aren’t interested in the potential volatility of an inexperienced coach.

Bleacher Report’s Jake Fischer claims Boston is focusing primarily on experienced candidates.

“The next person to lead Boston onto the parquet will have an immediate expectation of overseeing long postseason runs each spring,” Fischer wrote. “With that in mind, there’s little belief, sources said, that the Celtics’ next coach will be an assistant elevated to the top position for the first time.”

Fischer’s report hasn’t stopped the Celtics from seeking out long-time assistants. ESPN’s Adrian Wojnarowski reported that Stevens received permission to interview Los Angeles’ Chauncey Billups, Milwaukee’s Darvin Ham and Charles Lee, Dallas’ Jamahl Mosley, and Brooklyn’s Ime Udoka. None of those men have head coaching experience.

While Billups has a lengthy résumé as a player, the Milwaukee duo has turned heads for several years.

“Mike Budenholzer, as you mentioned, it’s been a trickle-down effect because he came from the Popovich tree. Now Bud, he’s created his own tree. There is a Mike Budenholzer tree that is coming out in the NBA,” ESPN’s Malika Andrews said on an episode of Wojnarowski’s podcast. “I believe Charles Lee and Darvin Ham are going to be head coaches in this league. I think the league is starting to see it.”

“Those who have worked with him [Lee] say he has an intuitive sense of how to inspire improvement from players but also understands high-level strategy and the preparation required to implement it,” ESPN’s Kevin Arnovitz wrote last summer. “He is, in the words of one peer, someone who is “categorically going to be an NBA head coach.”’

Arnovitz also claimed Ham “would command the instant respect of current players with his voice and manner as a hard-nosed NBA vet. He also brings a strong development background as a longtime assistant to Budenholzer, who offers an annual clinic in the art of team building and management.”

It’s somewhat surprising that San Antonio’s Becky Hammon isn’t on Boston’s shortlist, considering her time spent as an assistant under Gregg Popovich. At one time, analysts believed Stevens would succeed Popovich as the NBA’s next great head coach. Yet the old master outlasted the upstart on the sidelines.

According to Wojnarowski, Boston did its due diligence in-house, interviewing Jay Larranaga, Jerome Allen, Scott Morrison, and Joe Mazzulla, who were assistants on Stevens’ staff.

It might take weeks or even months before the Celtics find the right candidate, but everyone in the basketball community knows Boston’s expectations. Failure is not an option. The front office wants championships. Fans anticipate parades and banners.

Heavy is the head that bears the burden of Boston’s future.

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Trading Kemba Walker

Boston traded Terry Rozier for Walker, hoping the All-NBA point guard could become a steady veteran star alongside Brown and Tatum. When the Celtics acquired Walker, he was 29 years old and coming off the best season of his career when he played in all 82 games. Since then, he’s averaged under 20 points per game and only made 99 appearances.

Walker was always mediocre on defense, but his sudden drop in availability and offensive production is the real issue. The 31-year-old makes $36 million in 2021 and has a player option for $37.653 million in 2022. That’s a lot of dough for an aging, injured, and undersized point guard that isn’t an elite facilitator or three-point shooter.

Walker could still return to form if he stays healthy, but the Celtics have larger roster issues they’d rather deal with than the former All-Star’s health. With Tatum developing into a superstar and Brown reaching All-Star levels in 2020, Boston doesn’t need a scoring-orientated point guard anymore. Walker no longer fits the team’s plans.

There are plenty of possible trades out there for Walker. His large contract makes trading for young players on rookie contracts impossible, but the Celtics could kick the tires on a few former stars.

If Boston looks at simple trades without many moving pieces, they could send Walker to Dallas in exchange for Kristaps Porzingis. The Latvian forward/center has the height to protect the rim and can space the floor on offense. The Celtics could reunite with Al Horford in the Walker trade or throw in some draft picks for a shot at CJ McCollum.

More complex scenarios might involve the New York Knicks sending Derrick Rose to Boston in a sign-and-trade. The Miami Heat could perform a sign-and-trade with Goran Dragic and other veteran assets. Kevin Love’s name always comes up this time of year, but he’s never traded. The Celtics should also look into trading Walker for a three-point ace, like Buddy Hield.

Celtics fans hope there’s a way Stevens can convince Portland to take Walker and a mountain of draft picks for Damian Lillard. Don’t hold your breath.

Boston Celtics Free Agents

Evan Fournier, Luke Kornet, and Semi Ojeleye are unrestricted free agents, while Tacko Fall and Tremont Waters are restricted free agents. Fournier was the only member of that group to log over 1,000 minutes played last season. The 28-year-old joined the Celtics in a trade with the Orlando Magic, but he could turn into a half-season loan.

Fournier only suited up for the Celtics in 16 games this regular season. The French guard predictably took fewer shots and scored fewer points in Boston than in Orlando, but he became one of the team’s best three-point shooters. Unfortunately, adding Fournier didn’t provide the offensive spark Boston needed to overcome its mediocrity.

Over the past five years, Fournier has averaged 17.0 points, 3.2 assists, and 3.0 rebounds per game. He’ll gladly take a lucrative deal elsewhere if the Celtics don’t have enough money to pay him.

At 7-2, Kornet is a towering interior presence. However, he only appeared in 18 matchups for Boston and averaged 14.1 minutes per game. The Celtics don’t view Kornet as an integral part of their team moving forward.

On the other hand, Ojeleye played in 254 games since arriving in Boston as the 37th overall pick in 2017. He set career-highs in minutes (17.0), points (4.6), assists (0.7), and rebounds (2.6) per game this season. Those numbers hardly make Ojeleye a standout player, and the former Duke transfer hasn’t posted a positive box plus/minus over an entire season in his career.

Waters only played 357 minutes during his two seasons with the Celtics. Fall saw the court even less, only logging 169 minutes in 26 appearances. At 7-5, Fall is a unique athlete, but the giant’s lack of body control and speed make him unusable in close games. Stevens might push for keeping Fall around for another year or two, but he doesn’t have a long-term future in Boston.

Cap Space and Free Agent Targets

The NBA set its salary cap at around $109 million this season, with the luxury tax set at $132.6 million. Spotrac estimates the Celtics owe their four highest-paid players about $105.217 million for 2021, while the rest of the roster drags that amount up to roughly $134.856 million. Various exceptions could create more space, but Boston doesn’t have much wiggle room.

The Celtics have several glaring holes on their roster. They need a defensive seven-foot center. Tristan Thompson isn’t cutting it, and neither was Daniel Theis before him. Robert Williams is excellent defensively, but he’s undersized. An offensive facilitator and more three-point shooting should make life easier on Brown and Tatum.

Given Boston’s cap situation, the Celtics can’t chase any big-name free agents this summer. They might end up preoccupied trying to re-sign Fournier or allocate time extending Marcus Smart and Williams. Stevens should go bargain bin hunting over the coming hectic months and see if he can land a gem or two.

While Boston desperately needs players like Nerlens Noel and Duncan Robinson, it seems more likely that the C’s settle for Josh Hart, T.J. McConnell, or Hassan Whiteside. Maybe injuries and age push Serge Ibaka, Paul Millsap, or Otto Porter Jr. into Boston’s range.

Celtics fans want their team to chase John Collins and Spencer Dinwiddie. Boston doesn’t have a shot at landing either of those players on the open market. Any star additions must come through sign-and-trades.