What should the Boston Celtics' big takeaway be after watching the Milwaukee Bucks win the 2021 NBA title? Well, it's quite a luxury to have the best player in basketball and watch him elevate to a whole new level on the championship stage like Giannis Antetokounmpo did.
But our minds tend to rewind to the 2020 offseason when, after being stiff-armed short of the Finals stage in consecutive years and pondering ways to ensure Antetokounmpo would stick around long-term, the Bucks splurged to acquire Jrue Holiday.
The Celtics should hope they have their own Antetokounmpo-Khris Middleton tandem in Jayson Tatum and Jaylen Brown. The lingering question: How does Boston fill out the roster around them and, as the Celtics’ All-Stars continue their own development, is there enough talent in-house or does this team need its own Holiday-like pursuit?
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The good news for Boston is that Brad Stevens’ initial tinkering after elevating to president of basketball operations has positioned the Celtics for multiple avenues to building out the roster and adding talent.
But what exactly is the best path forward to a Holiday-like addition?
Keeping the books clean for a big-splash signing
A curious summer looms after Boston got a jump-start on the offseason by dealing Kemba Walker to Oklahoma City. The big decisions in front of Stevens: Does he re-sign trade deadline acquisition Evan Fournier — or more importantly, for how much and how long — and does the team offer contract extensions to Marcus Smart and Robert Williams?
The Celtics have only $72 million in guaranteed money on their books for the 2022-23 season. If the Celtics limit offseason spending — or simply put a focus on short-term deals — and resist the urge to extend eligible players, then there is a road map to near-max cap space as early as the summer of 2022.
This path is thorny, however, and requires 1) Moving on from both Smart and Fournier before any free-agent splurge could occur and 2) Moving the partially guaranteed final year of Al Horford’s deal. The Celtics could wait to decide on Williams’ future, though that’s a bit of a dice roll if he has a big year before hitting restricted free agency.
Still, with proper diligence, the Celtics could be major players in pursuing a top-tier free agent. An example: If Bradley Beal declines the final-year player option on his current deal, the Celtics could sign him in free agency next summer to move forward with a core of Tatum, Brown, and Beal while potentially having Williams, Romeo Langford, Aaron Nesmith, and Payton Pritchard for depth.
The road map to max cap space is even more agreeable for the summer of 2023 when Tatum and Brown are the only guaranteed money on the books. The downside: Two years is an eternity in the NBA and Brown would be entering the final year of his contract by that point.
Splurge now, trade for a star later
Given the potential pain points on the road to a free-agent signing, Boston’s more likely path to adding the missing ingredient almost certainly is a trade.
If content to muddy the books a bit now, the Celtics could splurge this summer, examine how the current mix of players performs in a more normal season, then plot a course forward.
On this path, the Celtics retain Fournier and extend both Smart and Williams. All three players end up with healthy paydays and push the C's into the luxury tax, but all three also would become attractive trade assets who might give Stevens additional avenues to pursuing big-ticket talent.
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Boston also could straddle these paths a bit. They could overpay Fournier if he’d return on a shorter-term deal -- something like a 1+1 or 2+1 deal with option years that could help the Celtics swerve back into the cap-space lane with some additional maneuvering.
If the Celtics pay to retain Fournier, Smart, and Williams, it would afford Stevens some flexibility in constructing trades. Instead of being limited to offering Horford’s partially guaranteed deal and a swarm of picks, the Celtics would be able to offer something like a Fournier/Williams combo to get near $30 million in salary, and that might be more attractive to a team swallowing hard while moving a disgruntled star.
The hard part is figuring out who exactly should be Boston’s Holiday. Some of that hinges on whether Williams stays healthy enough to blossom into the impact center he clearly can be. If landing Beal is the key to ensuring Tatum’s long-term future in green, then that has to be a consideration as well. Otherwise, it’s just finding the player who best complements the Tatum/Brown pillars — which would seemingly be a playmaking point guard.
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While nothing about the 2020-21 season suggests that we should be particularly bullish about the Celtics’ chance of competing with only minor tinkering, we are somewhat intrigued to see what this team looks like next year if it does elect to simply pay to retain its core players.
If Tatum and Brown take another step forward, if Fournier finds more of a comfort level in Boston, if Smart gets back to being an All-Defense talent who thrives in the starting point guard role, if Williams stays healthy, and if the recent draftees make strides then this team is not devoid of talent.
But that’s admittedly a lot of "ifs" -- the same sort of ifs that the Bucks were pondering before they made their own big-splash move.
And that’s the big challenge moving forward for Stevens: Can he find Boston’s Holiday?