3 bold trade targets the Milwaukee Bucks could pursue by the trade deadline

The Milwaukee Bucks are entering an inflection point. Giannis Antetokounmpo is now in his late athletic prime which means the doomsday clock has begun ticking on his time as an elite player. Anyone not named Damian Lillard or Antetokounmpo has been discussed as a possible trade candidate. The entire roster should be at DEFCON 5.

A year and a half into the Giannis-Lillard duo and they’re still subordinate to the Knicks, Celtics, and Cavaliers. Lillard isn’t getting any younger, Khris Middleton isn’t getting healthier or more agile, and Antetokounmpo is bound to get more restless.

With the trade deadline approaching, Jon Horst should be pumping some iron and getting ready to do some heavy lifting. I've been stretching the trade muscle too. Here are three bold trades the Bucks should consider to pump some blood flowing back into this team’s atrophying title aspirations. 

Jimmy Butler 

Now is not the time to be safe rather than sorry. The Bucks have had their share of wars with Butler. He’s a certified postseason game wrecker and the enemy of thy enemy is thy friend. The East is stacked with talent. Butler might be enough to put them over the edge.

The Miami Heat’s embattled star has allegedly expressed private disinterest in playing in Milwaukee. His sights are set on Phoenix. However, Lillard was once set for Miami. Once Lillard arrived in the Cream City, he settled in without incident. They can finally unite in Milwaukee. Butler is not without risk. The overly optimistic perspective is that Butler has been adamantly opposed to being traded to Memphis or Milwaukee because he’s executing a reverse psychology strategy aimed at Pat Riley who is petty enough to send him to either franchise as a punishment. It’s optimistic, bordering on delusional. The review board’s opinion is still out.

The obvious downside is that Butler is a generational hellraiser when he’s unhappy with his circumstances and if he gets traded to Milwaukee he could come kicking and screaming. On the hardwood, Butler is still a dynamic secondary playmaker who can make it work in any lineup as a scorer, facilitator, and most importantly a wing defender. The Bucks desperately need a hardwood polymath to fill the minutes around Lillard and Antetokounmpo. Their roster has a stockpile of shooters and spot-up shooters, but few can do both. 

As it stands, Milwaukee has been stuck in amber while the top seeds have taken quantum leaps. Not tinkering will be able to push them back into the league’s elite. The Giannis era is slowly fading and Butler is the adrenaline rush they need. Butler goes everywhere for a good time, not a long time. Eventually, his act wears thin and he blows it up, but for the first few seasons, he has been an asset on every franchise he’s wound up on.

Jerami Grant

The Blazers veteran forward was a teammate of Damian Lillard in Portland which gives him the familiarity advantage. Most importantly, he’s an ideal 3-and-D forward for Milwaukee. This season, Grant's scoring is down as he's averaging 14.7 points per game, and his efficiency has slumped to 38 percent shooting from the field and 38 percent from behind the arc. However, in the two years prior he was dropping 20 a night on 45/40 splits. This would be Grant's worst shooting season in eight seasons which has lowered his trade value, but given his history, this is merely a slump.

In addition to improving the floor spacing without sacrificing defensive intensity, Grant doesn’t take the ball out of Antetokounmpo or Lillard’s hands to put in work. As a primary or secondary scoring option, Grant has been found wanting, but as a tertiary scorer, he'd plug in nicely. Grant has three years and $102 million left on his contract and the last time he was on a contender, he was instrumental in a support role en route to Nikola Jokic’s first trip to a Western Conference Finals. He was ill-suited for starring roles in Detroit or Portland. Grant is an ensemble castmate who can defend the 1-5, a defensive versatility the Bucks are sorely lacking. For good measure, the Bucks get to audition him tonight in Portland.

Jordan Clarkson

Retire the microwave scorer label. Clarkson is the ultimate Netflix binge-scorer with a hint of playmaking mixed in. He offers much of what Bradley Beal does but is wrapped in an annual contract that compensates him at a third of Beal’s earnings. He’s due just $14 million annually this season and next making it less of a hassle to assemble an offer while potentially keeping them from remaining over the second apron at season’s end. The Bucks were given a first-hand view of what Clarkson delivers when he heats up on Monday night.

Clarkson’s inexpensive contract would also give Milwaukee flexibility to consider a second trade for a starter or role player or they could acquire him without surrendering Khris Middleton who has found his sweet spot on the second unit. Utah has been involved in trade rumors involving them offloading talent since the offseason even if the exodus from the team buried at the bottom of the West hasn’t happened yet. It’s just a matter of exchanging a young player or picks Danny Ainge would want.