Milwaukee Bucks News

Home

Quizzes

Watch

Newsletter

Discarded Bucks wing gets second chance on 2-way deal with Cavaliers 1 Mar 19, 2023; Greensboro, NC, USA; Kentucky Wildcats forward Chris Livingston (24) reacts to a basket during the first half against the Kansas State Wildcats in the second round of the 2023 NCAA men’s basketball tournament at Greensboro Coliseum. Mandatory Credit: Bob Donnan-USA TODAY Sports

Discarded Bucks wing gets second chance on 2-way deal with Cavaliers

Originally posted on WI Sports Heroics | By John Sbisa | Last updated Oct 31, 2025 5:30 PM ET

Former Milwaukee Bucks wing Chris Livingston has found a new home with an Eastern Conference rival, the Cleveland Cavaliers, on a two-way deal, reports ESPN’s Shams Charania.

The last three and a half months have been a roller coaster for the third-year player out of Kentucky, from off the Bucks’ roster to a new guaranteed contract, to being cut again. What kind of opportunities Livingston will have in Cleveland remains to be seen. Probably, any chances he does get won’t be much better than the scant playing time he saw in Milwaukee. Still, he deserved another shot somewhere after slogging through a brief Bucks career whose timeline reads like a brutal trick-or-treat prank.

Up-and-down Bucks tenure failed to pay off for either side

Actually, although his time in Milwaukee did not do much for career, it did pay financial dividends for Livingston. Getting a $2.3 million guaranteed contract based on a strong Summer League performance, then failing to show enough to make the team three months later effectively amounts to a legalized hit-and-run.

The Bucks could have kept him, of course, but ultimately decided it was worth eating his guaranteed money in order to hold onto Andre Jackson Jr. and Amir Coffey. Cutting either of the latter, whose preseason contracts were partially or fully non-guaranteed (Coffey’s still is), would have saved them something. They just didn’t see enough in Livingston to justify keeping him around.

In two years, Livingston didn’t get them much reason to. The former 58th overall pick played 42 games averaging only 4.7 minutes per contest and 1.3 points. He has the size and strength but not the quickness to guard threes and twos. At 6-foot-6, he is undersized for a four. He can bully his way to the free-throw line against smaller defenders, but doesn’t have great shooting touch or passing skills. He does not really fit into any one position.

Discarded Bucks wing gets second chance on 2-way deal with Cavaliers 2 Apr 12, 2024; Oklahoma City, Oklahoma, USA; Oklahoma City Thunder guard Aaron Wiggins (21) shoots beside Milwaukee Bucks forward Chris Livingston (7) during the fourth quarter at Paycom Center. Mandatory Credit: Alonzo Adams-USA TODAY Sports

After he failed to appear in either of the Bucks’ final two preseason games, the writing was pretty much on the wall. What follows is a timeline of Livingston’s ultimately futile stay in Milwaukee:

June 2023: Drafted in the second round after one season at Kentucky

July 2023: Signed a four-year rookie deal worth $7.6 million, $3 million guaranteed

2023-2025: played sparingly for the Bucks, mostly in garbage time, as well as for Milwaukee’s G-League affiliate Wisconsin Herd. Good numbers there and in Summer League never translated to the NBA level.

July 2025: Waived

July 2025: re-signed for one year and $2.3 million

October 2025: waived again

October 2025: signed a two-way deal with Cleveland

Discarded Bucks wing gets second chance on 2-way deal with Cavaliers 3 Mar 17, 2023; Greensboro, NC, USA; Kentucky Wildcats forward Chris Livingston (24) shoots against the Providence Friars in the second half at Greensboro Coliseum. Mandatory Credit: Bob Donnan-USA TODAY Sports

After all that, Livingston is still just 22 years old. It didn’t work out in Milwaukee, but maybe a change of scenery will get his NBA career off the ground.

This article first appeared on WI Sports Heroics and was syndicated with permission.

More must-reads: