Milwaukee Bucks Roundtable: Previewing crucial free agency

3. What would you say is your biggest concern heading into free agency?

BS: My biggest concern is that the ownership group baulk at paying the tax and let Brogdon and Lopez walk, in favor of signing cheaper guys on the market. Letting two starters walk would be catastrophic for this team in a season where they MUST do all they can to convince Giannis Antetokounmpo to sign long term.

DL: What do the Bucks do if they lose Malcolm Brogdon? The only player out of the major free agents they have that hasn’t made it clear he wants to stay here is him. What if he tries to make his way out Milwaukee? What’s their plan B given that they won’t have enough cap space to find an adequate replacement for him?

Brogdon’s money, given his health history, could also lead them to walk away. As I said on the Win In 6 Podcast this week, the Bucks could have a walkaway number that they won’t match. Brogdon is the player to watch out of the three free agents. How his market plays out will have a major bearing on how the Bucks’ offseason is perceived.

IS: I agree with Dan — losing Brogdon, who is the best fit on the team, would be bad for chemistry and production. An even worse case scenario is missing on Malcolm and George Hill, leaving the Bucks thin at guard behind Bledsoe. There’s young guys, obviously, who have played well in stretches, but Hill and Brogdon are talented veterans, which are key to deep playoff runs.

JT: Like both Dan and Isaac, Brogdon’s restricted free agency has been fascinating to watch. However, my concern over the speculation that the Bucks are bracing for a big offer sheet/have a walk away number has cooled off significantly, given how free agency is already playing out. That doesn’t mean that either don’t exist or that the Bucks may think long and hard about a lucrative offer sheet from another team around the league, but I’m coming around on Brogdon’s free agency not being as big of a threat to the Bucks’ current window than previously thought.

SR: I still would say Brook Lopez, despite the rumors of motivation to work out a new deal. Until I hear that it’s done, he will remain my top concern. With Middleton, the Bucks can offer the most money, and with Brogdon, they have control over his restricted free agency. On Lopez, there’s neither. He has all the leverage, and will be in demand.

AM: My biggest concern is penny-pinching. The most obvious way in which that could present is if they were to let Brogdon walk due to a hefty offer sheet coming in from elsewhere, but it would be just as troubling if they were to return their core and then work to cut corners in other ways.

For example, dumping Ersan Ilyasova, when the availability of stretch 4s is incredibly scarce on the open market, simply to reduce a tax bill would be a major red flag. If you’re going all in on paying your best players and you have a route to quality depth behind them, don’t deplete that secondary group. The Bucks are likely making more money than they’ve ever made in their history. Now is the time to pay the tax.