SportsMoney Milwaukee Bucks Ultimate Offseason Guide: Free Agents, Salary Cap Situation And More Brian Sampson Contributor Opinions expressed by Forbes Contributors are their own. I use film and analytics to cover the Milwaukee Bucks. May 31, 2022, 03:08pm EDT | Share to Facebook Share to Twitter Share to Linkedin Boston - May 15: The Bucks Giannis Antetokounmpo (right) and Jrue Holiday (left) are pictured late . . . [+] in the game as the Celtics lead became insurmountable. The Boston Celtics host the Milwaukee Bucks in Game 7 of the Eastern Conference semi-finals between the Celtics and Bucks on May 15, 2022 at TD Garden in Boston. (Photo by Jim Davis/The Boston Globe via Getty Images) Boston Globe via Getty Images The Milwaukee Bucks face yet another pivotal offseason, as they try to maximize Giannis Antetokounmpo’s prime with their current core and supporting cast. Following their seven-game second-round defeat at the hands of the Boston Celtics, the Bucks and their fans are left wondering what if? What if Khris Middleton had been healthy, would their championship reign have ended in this fashion? That’s a dangerous road to go down, and the front office must now look forward and focus on improving the team. Idle hands are the devil’s playground. Milwaukee can’t afford to play the what if game and hope that’s enough to get the job done in 2022-23. Bucks Upcoming Free Agents The first order of business will be geared toward Bobby Portis and Pat Connaughton—two reserves who are expected to decline their player options this summer. Portis spent most of the 2021-22 campaign in the starting lineup as Brook Lopez was out due to a mysterious back injury. Although he personally excelled in that role—a career-high 14. 6 points and 9. 1 rebounds per game—it’s clear Milwaukee is at its best as a team when he’s coming off the bench. He already sacrificed oodles of money to return to Milwaukee last year so don’t expect him to go that route again—he’ll almost certainly decline the $4. 6 million player option he has for the 2022-23 season (a decision he has to make by June 29th). Milwaukee can offer him a bit more money this time around—a deal between two and four years, starting at $10. 9 million in year 1—even if it’s less than what he’ll get on the open market. Connaughton, the other major free agent, is a bit more straightforward. He, too, has a player option that he’ll very likely decline, as it’s only worth $5. 7 million. Although Milwaukee can offer him up to 30 percent of their cap to re-sign him, ESPN’S Bobby Marks expects him to get between $8-10 million in a multi-year deal. Connaughton was another vital piece to the Bucks’ thin bench and they can’t afford to lose him from the rotation. MORE FOR YOU WWE Extreme Rules 2021 Results: Winners, News And Notes As Roman Reigns Beats The Demon The World’s Highest-Paid Soccer Players 2021: Manchester United’s Cristiano Ronaldo Reclaims Top Spot From PSG’s Lionel Messi The Good, Bad And Ugly From The Green Bay Packers’ Win Over The San Francisco 49ers Thanasis Antetokounmpo (player option), Serge Ibaka (unrestricted free agent), Wesley Matthews (unrestricted), Jevon Carter (unrestricted), and Jordan Nwora (restricted free agent) are the other free agents of note. It’s very reasonable to assume Antetokounmpo will exercise his option while Matthews returns on a veteran minimum deal. Ibaka is likely gone while Carter and Nwora remain wildcards as to whether they’ll return to Milwaukee next season. Bucks’ Extension-Eligible Players With Middleton on the books for $38 million next season and a player option worth $40. 4 million in 2023-24, he and the Bucks have two paths to a contract extension this summer. Between July 11th, 2022 and the day before opening night, the two sides could come to an agreement on a deal for up to three years and $152. 5 million as an addition to his current contract. However, if Middleton were to decline his player option, Milwaukee could sign him to an extension for up to four years and $200. 9 million—an option that is on the table from July 11th, 2022 until June 30th, 2023. The first year of that extension couldn’t be for less than the $40. 4 million he turned down on his player option. The preferred path for the Bucks would presumably be that Middleton plays out his current contract, including exercising his player option, and then the two sides agree to an extension for less than the maximum allowed. Middleton will be 33-years-old before the 2024-25 season begins with plenty of mileage on his legs. The Bucks would likely be leery of signing him to a monster deal at that age. Brook Lopez is the other veteran who is eligible for a contract-extension. He’s entering the final year of his deal and is due $13. 91 million in 2022-23 before becoming an unrestricted free agent. Milwaukee could tack on another four years and up to $74. 7 million via an extension. Although the Bucks will be interested in retaining his services, don’t expect it to come anywhere close to the maximum allowed due to his age and the fact he missed 69 games last season while recovering from a back injury. Bucks Salary Cap Situation (Player and 2022-23 salary) Giannis Antetokounmpo ($42. 49 million) Khris Middleton ($37. 95 million) Jrue Holiday ($33. 67 million) Brook Lopez ($13. 91 million) Grayson Allen ($9. 35 million) Pat Connaughton ($5. 73 million player option) Bobby Portis ($4. 56 million player option) George Hill ($4 million) Thanasis Antetokounmpo ($1. 82 million player option) Rayjon Tucker ($1. 82 million non-guaranteed) Luca Vildoza ($1. 75 million non-guaranteed) Sandro Mamukelashvili (Two-Way) Guaranteed Salaries: $155. 97 million Non-guaranteed Salaries: $3. 57 million Total Salaries: $158. 71 million Luxury Tax Space: $9. 7 million over Team Assets $6. 4 million Taxpayer Mid-Level Exception 24th overall selection in 2022 NBA Draft (can’t trade until draft day) 2023 own second round pick and less favorable of Golden State or Cleveland 2024 own second round pick and Portland’s second round pick 2025 second round pick from Indiana 2027 own second round pick Earliest first round pick to trade is 2029 $6. 3 million in cash to send or receive in a trade $1. 52 million trade exception Team Needs Bench scoring Frontcourt depth Defensive wing with size Backup point guard who can create shots Three-point shooting Follow me on Twitter . 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