The Milwaukee Bucks appear to be on the verge of making their first move of free agency, as Marc Stein reports that they are closing in on a deal with combo guard Jerryd Bayless. The 25-year-old free agent averaged 10.1 points on 41 percent from the field and 39.5 percent shooting from three last year with the Boston Celtics. He previously had stints with the Blazers, Hornets, Raptors, and Grizzlies over his first five seasons.
It was no secret that the Bucks were thin in the backcourt, and were pretty likely to add at least one person to throw into the rotation with Brandon Knight, Nate Wolters, and O.J. Mayo. Bayless may not be a terribly inspiring addition, but he shouldn't really be a threat to take tons of minutes away from the young players and won't cause too much damage to the Bucks cap situation.
Milwaukee had recently been rumored to have a bit of interest in Suns restricted free agent Eric Bledsoe, so this signing initially appears a bit odd. The move basically rules out the Bucks making a straight up, "take it or leave it" offer for Bledsoe (update: see note below), but there's still a possibility for a sign-and-trade should the dominoes fall and Bledsoe becomes available. It's also entirely possible that the Bucks front office already explored this option and got shut down, leaving them to look at some cheaper, less flashy options.
Update (Frank Madden): We should note that aside from the roughly $12 million in cap space the Bucks have available to them, Milwaukee also would have the $2.7 million room mid-level exception at their disposal. Unlike the regular mid-level exception and bi-annual exception, the room exception does not have to be renounced in order to maximize cap space. Thus, depending on how the Bucks structure the rest of their summer, they could offer Bayless up to a two-year deal starting at $2.73 million without needing cap space to do it. Thus, this doesn't necessarily preclude ongoing interest in Bledsoe from a financial standpoint, though it would incentivize the Bucks to delay officially signing Bayless (if he was indeed signed for $2.7 million or less) until after any other moves have been made.
On the court, Bayless is a capable combo guard off the bench but not much more. He's a competent three point shooter (35.3% career), though his improved marksmanship in recent years has also coincided with a tumbling free throw rate. That's probably a result of playing more off the ball and generally having less freedom to attack defenses, though at the age of 25 he could certainly still have a rebound year left in him. All told, his shooting efficiency has tanked from a career-best 56.1% true shooting in 11/12 with Toronto to below-average marks of 51.4% and 49.8% the past two seasons, and along with it his catch-all metrics have similarly declined. A career-best 18.0 PER and .139 WS/48 in Toronto has dipped to pedestrian 12.0 and .069 a year ago, while ESPN's RPM data show him 56th overall among 84 point guards with a -2.68 real-plus minus. Interestingly, he rated positively offensively (+0.84) but a major negative defensively (-3.68). Overall those numbers put him slightly ahead of Brandon Knight (-3.18), slightly worse than Ramon Sessions (-2.08) and well below Nate Wolters (+0.03).
In terms of grading the signing, everything ultimately comes down to value. You're not likely to find anyone notably better for less than $3 million per season, so using the room exception without impinging on the Bucks' cap space would seem like a reasonable way to add some depth to a thin backcourt while still maintaining cap flexibility. If the price is higher (or officially happens sooner) and thus cuts into the Bucks' cap space then feel free to be a bit more skeptical.