Milwaukee Bucks: How Brandon Jennings’ free agency changed franchise’s trajectory

MILWAUKEE, WI - APRIL 25: Brandon Jennings #3 of the Milwaukee Bucks in action against the Miami Heat during Game Three of the Western Conference Quarterfinals of the 2013 NBA Playoffs at Bradley Center on April 25, 2013 in Milwaukee, Wisconsin. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Mike McGinnis/Getty Images)
MILWAUKEE, WI - APRIL 25: Brandon Jennings #3 of the Milwaukee Bucks in action against the Miami Heat during Game Three of the Western Conference Quarterfinals of the 2013 NBA Playoffs at Bradley Center on April 25, 2013 in Milwaukee, Wisconsin. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Mike McGinnis/Getty Images) /

The present for the Milwaukee Bucks would not have been made possible without Brandon Jennings and traversing through his tricky restricted free agency in the summer of 2013.

Long before they struck gold with a raw, long-limbed teenager coming out of Greece, the Milwaukee Bucks placed their bets on another wiry teenager through the draft who had played overseas a few years prior.

Then a highly sought-after recruit from Compton, who some scouting sites such as ESPN pegged as the top recruit in his class, Brandon Jennings made the stunning decision to play overseas instead of going to college to maximize his earnings and get battled tested along the way with a EuroLeague club, through the help of the legendary Sonny Vaccaro.

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Eventually settling on Roma, Jennings’ time in Italy served as one big crash course that forced him to cut his teeth going against experienced veterans.

Despite the ups and downs he experienced in his year abroad, the Bucks under general manager John Hammond tabbed the 19-year-old with the 10th overall pick in the 2009 NBA Draft, though ESPN’s Chad Ford reported later that year the Bucks had settled on selecting UCLA Jrue Holiday before reversing course:

"Just hours before the draft, things started to turn Jennings’ way. The Bucks had been on the fence between Jennings and Jrue Holiday. For much of the past month they had been leaning toward Holiday, but in the final 24 hours they began to have a change of heart.“Jennings has so much upside,” a Bucks source told me hours before the draft. “Sometimes you have to gamble a little. The great teams take calculated risks. I think we need to take a calculated risk.”"

Jennings entered the league ablaze and went on to author the Bucks’ very own version of a double-nickel game seven games into his NBA career and still stands as the youngest player to score 50 or more points in an NBA game.

But as the story goes, Jennings’ grand entrance into the NBA raised incredibly lofty expectations that inevitably set him up to fail, due to his incredible streakiness and the bad breaks and moves made on the part of the Bucks’ management. As the Bucks failed to get out of second gear in their once-thought of rebuild, the table was set for a fascinating set of negotiations as Jennings became extension-eligible heading into his fourth NBA season.

As he saw draft class mates and fellow point guards such as Ty Lawson and Steph Curry lock down rookie extensions with their teams in the lead up to the deadline, the reported four-year, $40 million offer put forth by the Bucks was declined by Jennings and his representation as Yahoo! Sports’ Marc Spears reported in March of 2013.

From there, the Bucks elected to not pursue or continue to deliberate with Jennings on an extension offer, which left him hungry to show the Bucks and all 29 teams what he can do as he told Charles Gardner of the Milwaukee Journal Sentinel October of 2012:

"“I’m going to just play this year out and do what I have to do here,” Jennings said. “The main goal is still trying to win, still trying to make the playoffs.“Then I’ll be able to make my own decision. The main thing is, I could say I’m kind of auditioning for other teams, too. The fact if they see what I can do, what I can bring to the table this year for the Bucks, anything can happen in the summertime. Now I’m just going to take it for what it is and ball out, man. Take this as it’s my rookie year again.“Take it that I’m the fresh meat that nobody’s ever seen play.”"

As Jennings continued to largely offer up the same inefficient scoring within a Bucks team that hit new heights of mediocrity during the 2013-13 season, Jennings made his intentions clear he was looking for a very nice payday and at all literal costs.

Ford reported for ESPN ahead of the February 2013 NBA trade deadline that Jennings had fired his agent Bill Duffy, who had presided over extension talks the previous fall, and sought either a trade or a massive offer sheet in that coming summer:

"“Jennings has, according to one source, “irreconcilable differences” with Milwaukee. He’s frustrated, according to sources, that the two sides weren’t able to work out a long-term extension this summer. In addition, he feels as though he doesn’t get the attention he deserves and wants a bigger market to take his talents to.Jennings isn’t bluffing. He recently changed agents in an attempt to get some traction on his relocation. Jennings’ marching orders for his new representation? Get him out of Milwaukee, either by the trade deadline or via a toxic offer sheet from another team this summer.”"

Jennings eventually took his negotiating tactics public as he threatened to play on his qualifying offer for the 2013-14 season from that aforementioned piece by Spears, which would then have led to him becoming an unrestricted free agent in the summer of 2014 under that scenario.

Needless to say, Hammond was skeptical of that happening:

"“It’s not unfair to make that statement if he feels there is not a deal fair to him this summer,” Bucks general manager John Hammond said of Jennings’ stance. “I would be surprised if it happens. But he is operating within the [collective bargaining] rules. I’m not taken aback. It’s a natural discussion to have.”"

Still, as Jennings continued to shoot arrows in the direction of the Bucks’ management and their proverbial bow, the Bucks continued to sink further in despair and unhappiness. Jennings, himself, was at the center of that following a late March loss to the Philadelphia 76ers where he was benched in the second half by interim head coach Jim Boylan, prompting this quote as Gardner reported after the game:

"“This is the third time I’ve been benched in the second half and it hasn’t been under (former coach Scott) Skiles,” Jennings said. “You always want to be out there to help your team.“I don’t see any all-stars in this locker room so I think everybody should be held accountable, like anybody else. There’s no maxed-out (contract) players in this locker room; there’s no all-stars. So don’t try to put me on a pedestal and just give everybody else the freedom to do whatever they want.”"

Milwaukee’s eventual flameout in their first round sweep to the Miami Heat in that year’s playoffs served as the fitting cap to Jennings’ time in Milwaukee to that point and with an offseason full of uncertainty ahead.

While the Bucks’ stance had long been that they would match any offer that came to Jennings once free agency opened, their actions said otherwise.

Following the moratorium being lifted, the Bucks offered Atlanta Hawks guard Jeff Teague a four-year, $32 million offer sheet, which the Hawks subsequently matched. All the while, Jennings twisted in the wind and the Bucks’ roster increasingly changed and the open market dried up all around him.

The world and more specifically, Indiana Pacers All-Star big man Roy Hibbert, waited in anticipation for where and when Jennings’ next move would be.

Eventually, Jennings’ wait ended on July 30, 2013 when the Bucks agreed on a sign-and-trade deal with the Detroit Pistons where, in exchange for Jennings, Milwaukee received Brandon Knight, Khris Middleton and Slava Kravstov.

According to Hammond as Sean Deveney of the Sporting News reported in November of 2018, it was the inclusion of Middleton in the trade package that had been a sticking point in talks between the two parties:

"“The Pistons did not want to include Khris in that deal,” said Magic GM John Hammond, who was with the Bucks at the time. “A lot of people considered him a throw-in in that deal, but Joe (Dumars) did not want to give him up. We knew what Khris had done at Texas A&M before he got hurt, so there was potential. Detroit did not want to give him up, but in the end they had to in order to make the deal work.”"

Later in that piece, Middleton talked about where he stood in the Bucks’ plans as part of the deal, fearing that he was just looked as salary filler:

"“My first reaction when I was traded was, am I going to be cut? Am I going to make it?” he said. “If you are a second-round pick and you get traded, you are kind of in limbo that way. You are starting over. … I talked to Joe Dumars after it happened and John Hammond when I got to Milwaukee. Both were saying that I wasn’t a throw-in there.“John Hammond told me they were starting over and they were just looking for players who could play. They were rebuilding, and he wanted to see if I could fit and earn a job.”"

Safe to say Middleton earned the job. The swingman has gone on to become a two-time All-Star who, along with superstar Giannis Antetokounmpo, has stood as one of the most prominent building blocks in the Bucks’ rebuild throughout the decade and obviously key to their glowing success over the last two seasons.

Knight, the then-centerpiece of the deal, played with the Bucks until he was dealt on the day of the 2015 trade deadline in a three-team deal between the Bucks, the Phoenix Suns and the Philadelphia 76ers. Despite never playing a regular season game, Kravstov still managed to become a Summer League legend with the Bucks in the summer of 2016.

Meanwhile, Jennings’ career took a drastic turn for the worse after he tore his Achilles midway through the 2014-15 season, during a game in Milwaukee of all places. His path eventually led him back to Milwaukee well into the 2017-18 season where he signed a pair of 10-day contracts and subsequently a multi-year deal to eventually bring his NBA career full circle, at least for the time being (Jennings is a free agent currently).

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As you see, the long and winding saga of Jennings’ restricted free agency easily could have gone in many different directions. While not the building block they may have once envisioned, the fact that the Bucks came out on top with an incredibly valuable player to show for it like Middleton goes to show that all the pieces matter.