Bayless will need a suit in a different shade of green next season, according to Marc Stein. (Photo by Jared Wickerham/Getty Images)
Bayless will need a suit in a different shade of green next season, according to Marc Stein. (Photo by Jared Wickerham/Getty Images)

According to ESPN’s Marc Stein, the Milwaukee Bucks are closing in on a deal with NBA journeyman guard Jerryd Bayless.

Bayless, a 6-foot-3, 200 pound combo guard, averaged 9.3 points per game while splitting last season between Memphis and Boston. He’s traditionally been an up and down 3-point shooter that teams have bet on hoping he could string together a few hot months. He’s been traded four times in his NBA career, twice in season.

Oh … and prepared to be stunned: Bayless is repped by Jeff Schwartz, Jason Kidd’s long time agent. I’m not saying that Kidd and Schwartz are running the show in Milwaukee, but I’m not saying that this seems like mere coincidence. I’m not sure this is the sort of power move Bucks fans who subscribed to the “Jason Kidd will help Milwaukee attract big names!” theory had in mind, but maybe it’s a start.

For the Bucks, Bayless could help provide depth at the razor thin guard spots. Boston Head Coach Brad Stevens last season referred to him as “kind of like a switch-hitter”, given his ability to play the one and the two. But he pointed out switch hitters in baseball are usually superior while batting at one side of the plate. For Bayless, he’s a better shooting guard than point guard. Over the last two seasons, he’s been basically a net zero as a shooting guard and a negative as a point guard, when judged by’s net PER by position.

As of Wednesday morning, Milwaukee’s guard positions are occupied by Brandon Knight, Nate Wolters, OJ Mayo and … there are no more clear cut guards on the roster. Khris Middleton can potentially help out at the two, though he’s a bit slow defensively there. Giannis Antetokounmpo the Point Guard is about to become Summer League’s hottest topic, if it isn’t already. So maybe Milwaukee is actually considering him have them ease some of their guard burden, but largely, Milwaukee doesn’t have guard depth. Bayless is a potential depth solution.

But the question that always pops into my head when a quasi-veteran signs with a rebuilding team: What is he getting out of this?

For Bayless, I suspect it’s an opportunity to rebuild value in a transitioning situation. He’s had teams try and turn him into a point guard and others let him run wild in his position, hoping to find a bench scoring solution en route to the playoffs, but he’s never been able to maintain consistency. Unless more transactions are to come, his role will likely be stable in Milwaukee, as he battles with Wolters for backup guard minutes. Perhaps he’ll be trade bait come February, but he’ll have a few months to get adjusted and earn a spot in the Bucks rotation.

In a situation where the coach isn’t all that familiar with the current roster and shares an agent with you, this fit does seem to make sense for Bayless. He could become Milwaukee’s third guard and average 25 minutes per game with a rebuilding team if everything breaks right for him. This is the new Bucks version of last year’s Gary Neal deal.

Except there are no grand organizational aspirations surrounding this signing (assuming Stein is correct and it happens). The Bucks and Jerryd Bayless both know what they are getting into.