The Bucks got a plethora of new players from trading Giannis Antetokounmpo to the Heat and have yet to see any suit up for Milwaukee yet. But they already need to make some big decisions regarding the futures of these former Miami players, starting with Tyler Herro's potential extension. However, extending Herro before next summer could decimate the Bucks' upcoming cap space and lead to more painful outcomes in the long run.
Herro's contract puts the Bucks in a tough spot
Herro will make $33 million next season and hit unrestricted free agency afterwards unless the Bucks sign an extension with him sooner. It's hard to gauge what the Bucks should offer Herro, since his value could vary a lot in a new situation. Still, the Bucks will probably want to go with the prevailing free agency strategy around the league and extend him early rather than risk losing him for nothing in a year.
That strategy has also made cap space generally less valuable, since teams can't just sign the best players as unrestricted free agents so easily these days. But next year could be different, with a huge amount of stars potentially eligible for free agency. There's still a lot of time for players to sign extensions, but as of right now, there's a lot of quality and depth among the potential free agent pool.
As a rebuilding team, the Bucks should be very interested in adding talent without having to give up any assets in return. But signing Herro to an extension worthy of his services will eat up a lot of cap space. In fact, it could even eliminate their flexibility for next offseason entirely.
The Bucks can't afford to lose Herro for nothing
On the other hand, the thought of losing Herro without getting anything back is gut-wrenching. Herro was one of the headliners of Milwaukee's return package for Giannis and that makes it even for imperative that Bucks get proper value out of him. He can provide that value through his role as a mentor and supporting piece in the development of younger players next season, but also in his value as a trade chip if signed to an extension.
If the Bucks get Herro on a solid deal, he could still be enticing for other teams in need of an additional creator in the backcourt. Dishing Herro for some solid draft capital or promising assets after a year in Milwaukee would be the ideal scenario for the Bucks. And their best shot at making Herro an attractive asset for that very situation is to lock him up on a team-friendly deal.
Even if it takes the Bucks out of the running for the top free agents next summer, they can still get a lot back from Herro by taking a measured and patient approach. The Bucks probably won't be ready to add a major star in free agency anyways, so swapping Herro for future assets seems like a safer bet.
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