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The Best Bucks Contracts of the Decade: Jerryd Bayless Drops In at 6

The former Arizona guard was a decent marksman of the Jason Kidd era

Milwaukee Bucks v Cleveland Cavaliers Photo by Jason Miller/Getty Images

Often lumped into the much-maligned “Kidd-Schwartz” expanded universe era of the Milwaukee Bucks front office, Jerryd Bayless actually stands as one of the savvier moves during that otherwise forgettable few years. Reflecting back, his first year was significantly less impactful than I remembered, but the contract made it plenty palatable. The former Arizona guard made his bones as a trusty backup whose 3-point shot improved while in Milwaukee, and he offered a bit of off-the-dribble creation the Bucks sorely needed from their guard position. As the 6th best contract of this exercise, he deserves some adoration.

Bayless’ arrival being credited to Jason Kidd isn’t lip service either, he literally stated it when the signing was announced.

“The thing that was most intriguing was Kidd,” Bayless said Thursday at the Bucks’ training facility. “He can help me in a variety of different ways. There aren’t a lot of guys like him that come around.”

Bayless was a one-and-done prospect early on in that era, when he led Arizona in scoring and assists as a freshman (the first time a freshie had done so in school history), then bolted to be selected 11th overall by the Indiana Pacers in the 2008 draft. He was shipped to Portland before he played a game at Bankers Life Fieldhouse. He bounced around, appearing for five different teams within his first seven years.

He was a bit player, never averaging double digit points per games for any season beyond an injury-shortened 2011-12 campaign for Toronto. As such, expectations were low for Bayless coming into Milwaukee, and his minimal salary hit reflected that.

Almost immediately, he became one of Jason Kidd’s key cogs off the bench. He appeared in 77 games, starting just four, and averaged 7.8 points to go with 3 assists. That year, Milwaukee boasted the 7th best bench in the league, averaging 37.3 points per game. Bayless was behind only O.J. Mayo in terms of scoring among that bench squad. One bugaboo, Bayless’s 3-point shot tanked to just 30.8%. I am not sure that was entirely his fault, as his 3-point shots per game (1.6) were the fewest since his sophomore campaign. Clearly, Kidd had different designs for Bayless’s game, a decision made even more curious by the about face the following season when Bayless was a flamethrower (43.7%) on 4.4 attempts per game. On catch-and-shoot attempts in particular, he was a lights-out 45.9%, fifth in the league among players who attempted 3 or more 3-point attempts of that variety that season.

To offset the horrid firing from deep, he had one of his better finishing years at the rim, 55% per Cleaning The Glass, around 50th percentile among point guards in 2014-15. That year, the Bucks also had a neutral net rating with him on the court in 2014-15, and a slight positive (1.1) when he was off. So, that first year was solid, but unspectacular. It did give us this instantly iconic walk-off in the Playoffs though, which is probably coloring my own perception of that season given I was in the stands.

In his second year, even with Milwaukee missing the Playoffs and Bayless missing thirty games, he was appreciably better. That was in particular due to the aforementioned improved 3-point stroke. Bayless gave Kidd a guard who could shoot from deep, a stark contrast to Michael Carter-Williams, and probably pointed towards the future with his capability to operate off-ball while Giannis handled the rock. Unfortunately, Bayless also offered little to nothing as a defender. Milwaukee’s defense was 4.1 points per 100 possessions worse with him on the court in 2015-16.

Still, for just 3 million a year, Bayless acquitted himself well enough those two seasons in Milwaukee to warrant his status as someone more than worth the minimal cost. Will he be remembered in the annals of Bucks history? Not for anything more than that buzzer-beater, but he served the Bucks well during his two years even if his PER nestled around a below-average 12. Milwaukee got his last best years, and at a steal. It’s just really too bad that Philadelphia paid him $27 million over the course of the next three years of his contract. Just an absolute shame...

From The Archives

Frank breaks down the deal from a cap perspective and performance standpoint. My favorite summation:

So while Bayless’ ability to knock down threes and fill in at either guard spot makes the 2008 lottery pick a solid fit with any of the Bucks’ other guards, he’s unlikely to make a noticeable impact for good or bad. Though his usage rate is comparable to Gary Neal’s, his assist rate is also about twice as high, so he’s neither a playmaker nor an unrepentant chucker. In short, the Bucks needed another guard to give them some semblance of depth in the backcourt, and Bayless gives them that. Don’t expect much more, but also realize that other options (Ramon Sessions, Jameer Nelson, Mo Williams, Jordan Crawford) were unlikely to provide significantly better value.

Brew Hoop Best Contract of the Last Decade Ranking

8. Zaza Pachulia (2013; 3-year, $15.6M)

7. Mike Dunleavy Jr. (2011; 2-year, $7.5M)

6. Jerryd Bayless (2014; 2-year, $6M)

Now that we’re getting closer to some more intriguing debates (from my view) about these couple contracts, I’ll be leaving the poll open until Thursday to give folks a little more time to weigh in.


What is the WORST contract out of this best bunch?

This poll is closed

  • 23%
    2015 Khris Middleton (5-years, $70M)
    (44 votes)
  • 52%
    2016 Jason Terry (The first time; 1-year, $1.5M)
    (98 votes)
  • 2%
    2016 Giannis Extension (4-years, $100M)
    (5 votes)
  • 1%
    2018 Brook Lopez (1-year, $3.3M)
    (2 votes)
  • 19%
    2018 Pat Connaughton (2-years, $3.3M)
    (37 votes)
186 votes total Vote Now

This poll will close at 10 am CST on Thursday, June 18.