Middleton, 23, played a key role in the Bucks' 41-41 record and playoff appearance. Last season, Middleton averaged 13.1 points, 4.4 rebounds and 2.3 assists per game while shooting 40.7% from three-point range.
Middleton joined the Bucks after being traded with Brandon Knight and Viacheslav Kravtsov from the Detroit Pistons in exchange for Brandon Jennings on July 31, 2013. He was drafted by Detroit in the second round of the 2012 NBA draft.
The new contract can officially be signed on July 9, when the league lifts a moratorium on player business.
Analysis: Milwaukee wasted little time re-upping with its most important free agent. The price tag on this contract may seem high given Middleton's low profile on a non-contending team, but it's a reasonable figure considering he may have earned a max offer sheet from another team. As the incumbent team, the Bucks had the benefit of offering more gross salary over the full five years, even if the deal is less lucrative on a per-year basis. Middleton offers value as a three-point shooter and wing stopper. The 23-year-old averaged over 13 points and shot more than 40% from deep last season and provides another versatile defensive cog to a roster already featuring plenty of length and athleticism. While it's not surprising Middleton fetched a hefty sum for his 3-and-D skill set, one could argue that the Bucks may have dipped a little too deep into their pockets for someone who lacks obvious superstar potential. At the same time, Milwaukee isn't viewed around the league as a desirable free agent destination, so consider this a sensible deal a year before other, perhaps lesser players will command more on the open market with a larger salary cap — Chris Johnson