Brandon Jennings seemed to throw his long-term future with the Bucks into question when he said in February he was "doing my homework on big-market teams." Jennings quickly backtracked a little, and more recently he's indicated a willingness to sign a long-term extension with Milwaukee. The 6'1" high-scoring point guard has never been an All-Star, and the Bucks have only made one playoff appearance in his three seasons with the team, but there are still compelling reasons for them to want to hang on to the player they took 10th overall in 2009.
Jennings made an early splash with a 55-point burst in just his seventh pro game, but averaged just 15.8 points per game for his first two seasons. He lifted that number significantly this past season, to 19.1, helped not only by 2.2 more shots per game, but by improved shooting as well. He's continually raised his field goal percentage, from 37.1% in his rookie year to 39.0% in 2010/11, and to 41.8% last season. His advanced metrics show similar upticks, as his true shooting percentage, PER and win shares per 48 minutes all show year-to-year improvement throughout Jennings' brief career.
The Bucks are looking forward to a full season of Jennings and Monta Ellis in the backcourt. While conventional wisdom might suggest Ellis would siphon some of Jennings' offense, that wasn't the case last year, as Jennings' scoring average and shooting percentage were both up after Ellis arrived in a trade with the Warriors. Ellis averaged more than four fewer points per game with the Bucks than with the Warriors last year, so it remains to be seen whether the pairing can work for both players. Unfortunately, the Bucks won't have the benefit of a sample size larger than last year's 21-game partial-season experiment if they want to sign Jennings to an extension, since the deadline to do so is October 31.
Milwaukee has never been a destination for top-flight free agent talent, so it makes sense for the franchise to do what it can to retain its own players, even if it has to overpay a little. Jennings turns 23 in September, and given his steady improvement, he could easily develop into an annual 20+ PPG scorer, a commodity at the point guard position. He's never been a high-assist player, topping out at 5.7 assists per game his rookie year, but his career assist-to-turnover rating of 5.4-to-2.3 suggests he can handle an offense with at least passable efficiency.
Based on Jennings' track record and potential, the Bucks can probably justify a four-year extension for the maximum. That would mean a first-year salary of 25% of whatever the salary cap is in 2013/14, when the extension would take effect, with 7.5% raises. That works out to about $14.5MM in the first year based on the current $58.044MM cap. In 2013/14, the Bucks will have $7.9MM committed to Ersan Ilyasova in the second year of his five-year deal, while Ellis has an early termination option worth $11MM for that season. Assuming Ellis stays with the Bucks and Jennings gets a max extension, that's $33.4MM for three players, which is not too expensive for the core of a team.
While Jennings, Ellis and Ilyasova are all under 30 and have room for improvement, no one's mistaking them for the cornerstones of a title winner. The Bucks have the flexibility to keep their team intact, but it's clear they'll need more. It's doubtful they can do much better than Jennings on the free agent market, but if they decide against extending him, or he decides to see what he can get from those big-market teams he talked about in February, he could be in for a tough go in restricted free agency.
Point guards Ty Lawson, Stephen Curry, Jrue Holiday and Jeff Teague could all become restricted free agents next summer, while Chris Paul, Jose Calderon, Mo Williams could be up for grabs as unrestricted free agents. Jennings could always sign his qualifying offer and become an unrestricted free agent in 2014, but that seems unlikely. A maximum extension appears to be mutually beneficial for both the Bucks and Jennings, and I expect agent Bill Duffy and GM John Hammond to come to an agreement soon.