Milwaukee Bucks, Giannis Antetokounmpo are betting their futures on each other

Ben Rohrbach
·5-min read

Jon Horst, the 37-year-old general manager of the Milwaukee Bucks, pushed his chips all in on building a roster that will convince two-time reigning MVP Giannis Antetokounmpo to sign his supermax extension.

The Bucks traded all they could to acquire Jrue Holiday and Bogdan Bogdanovic, a pair of not-quite-stars who are supreme basketball fits around Antetokounmpo and All-Star teammate Khris Middleton. It cost them Eric Bledsoe, George Hill, Ersan Ilyasova, Donte Divincenzo, D.J. Wilson, three first-round picks and two first-round pick swaps, according to ESPN’s Adrian Wojnarowski and The Athletic’s Shams Charania.

So, it better work. It has to work, because losing Antetokounmpo would be crippling to the franchise.

Boganovic will join the Bucks in a sign-and-trade deal that hard caps them at $139 million and is expected to pay him a starting salary close to $18 million. Milwaukee would be committing roughly $118 million this season to a starting lineup of Holiday, Bogdanovic, Middleton, Antetokounmpo and Brook Lopez. Only two other players will be under contract, leaving Horst to fill out the roster with bargain ring-chasing veterans.

So, this is their championship pitch to Antetokounmpo, for better or worse, and on paper it looks better.

Giannis Antetokounmpo works opposite his new teammate Jrue Holiday. (Jonathan Bachman/Getty Images)
Giannis Antetokounmpo works opposite his new teammate Jrue Holiday. (Jonathan Bachman/Getty Images)

Holiday has not made an All-Star appearance since his lone selection in 2013, but he was named to the All-Defensive teams in 2018 and 2019 and awarded Teammate of the Year honors this year. Averaging 19.1 points (on 46/35/71 shooting splits), 6.7 assists, 4.8 rebounds and 2.4 combined blocks and steals this past season, Holiday remained one of the game’s most underrated two-way players and a beloved veteran.

The 30-year-old has extensive experience playing both on and off the ball, both of which he will be asked to do alongside Antetokounmpo and as a playmaker in his stead. His only playoff appearance of the past five years was far more promising than the disappearing act Bledsoe made over the last three years. Holiday’s stat line of 24-6-6 on 58 percent true shooting in a 2018 first-round sweep of the Portland Trail Blazers is an afterthought, because his defensive work opposite Damian Lillard and C.J. McCollum was a masterclass.

Bogdanovic is another long and versatile wing best known for his shooting ability. The 28-year-old shot 37 percent on seven three-point attempts in 29 minutes a game last season, his third on the Sacramento Kings since leaving EuroLeague power Fenerbahce. Bogdanovic is another underrated playmaker, averaging 4.5 assists per 36 minutes for his career, and his effort defensively often masks his limitations on that end.

Together they should represent an upgrade for a team that was on pace to win 70 games for much of last regular season. But Milwaukee is losing several key pieces from that roster. Bledsoe was also a versatile guard and an All-Defensive bulldog at the point of attack. Hill led the NBA in three-point shooting, hitting 46 percent of his three attempts per game off the bench last season. Ilyasova and Wilson fell out of the playoff rotation, but DiVincenzo was a rising contributor. Holiday and Bogdanovic should eat most of their minutes.

According to ESPN’s Bobby Marks, the Bucks sent New Orleans the 24th pick in this year’s draft (via the Indiana Pacers), unprotected first-round picks in 2025 and 2027, and pick swaps in 2024 and 2026. Milwaukee also owes its 2022 first-round pick to the Cleveland Cavaliers, leaving Horst no future first-round draft assets to deal for additional upgrades. The franchise’s future is now fully invested in Antetokounmpo.

And if Antetokounmpo reciprocates, it will all be worth it. A supermax extension would keep the 25-year-old under small-market Milwaukee’s control through 2026 for upward of an additional $250 million, a price tag any team in the league would pay for the services of the game’s most dominant statistical force. Horst has given his superstar a roster he can win championships with, and that may be enough to secure a signature.

If he does not sign, there will be enormous pressure on Milwaukee to win this season. There will anyway, but the Bucks just bet this roster will deliver the titles Antetokounmpo so desperately seeks. Horst’s future — and all those first-round picks he has traded — depend on it. Without an extension, Antetokounmpo’s impending free agency will be a shroud over the season. The possibility both he and Holiday, who owns a player option for 2021-22, could walk at season’s end is the sort of anxiety that can send a team spiraling.

Nobody wants that. Antetokounmpo has a chance to be the rare modern superstar to invest in the team that drafted him and wager his prime on whether the front office just built a team that will make his legend.

According to The New York Times’ Marc Stein, “The last two weeks have been filled with chatter that Antetokounmpo indeed plans to sign his five-year supermax with the Bucks before the Dec. 21 deadline.” These deals point to a belief that Antetokounmpo will commit long-term when he gets his offer on Friday.

He better, because Horst just went all in.

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Ben Rohrbach is a staff writer for Yahoo Sports. Have a tip? Email him at rohrbach_ben@yahoo.com or follow him on Twitter! Follow @brohrbach

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