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Grade the deal: Butler's max contract caps remarkable personal journey

Chicago Bulls guard Jimmy Butler's bet on himself paid off big in free agency. 

The Most Improved Player is now in the running for Most Improved Bank Account.

Jimmy Butler and the Bulls have reportedly agreed to a five-year maximum rookie contract extension worth roughly $90 million, according to Yahoo Sports and USA Today Sports. The contract, which starts in 2015-16, reportedly includes a player option on the final season in 2019-20.

"Windy city skyline," Butler wrote on Instagram. "AKA home." 

Butler, 25, transformed from a defensive stopper into a two-way star in 2014-15, averaging a team-high 20 points, 5.8 rebounds, 3.3 assists and 1.8 steals per game. The last player selected in the first round of the 2011 draft, Butler was selected to the 2015 All-Star Game and the 2015 All-Defensive Second Team, as he helped guide the Bulls to the second round of the playoffs. His breakthrough as an all-around scorer was badly needed in light of multiple knee injuries to franchise point guard Derrick Rose, and his high motor and physical presence on the perimeter have made Butler particularly popular among Bulls fans.

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"Butler's a great player on [offense] and [defense]," United States President and former Illinois Senator Barack Obama wrote on Twitter. "Let's sign him up long term. Go Bulls!" 

Remarkably, this deal goes down as the rare no-brainer that is simultaneously a blunder. Last fall, Bulls management low-balled Butler with a four-year rookie extension offer worth roughly $40 million over four years. At the time, Butler was coming off of an injury-plagued 2013-14 season, and while he was a tenacious defender and workhorse, he had yet to showcase the ability to score efficiently or in volume. Apparently unconvinced that Butler would make a meaningful leap, the Bulls allowed talks to break down, as Butler famously declared the willingness to "bet on myself."

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That bet paid off in a major, major way for Butler and his Relativity Sports agent Happy Walters, and it burned the Bulls badly. Instead of having the foresight to lock up Butler on what could have instantly become one of the best value deals in the NBA, Chicago had no choice this summer but to pay an enormous price to retain one of its key building blocks. Now, the burden falls on new coach Fred Hoiberg to help the Bulls take the next step as a group, as management is not in position to make meaningful upgrades to the roster's core.

Even though "buy high" isn't an ideal strategy, Butler's play certainly warranted this decisive approach. Chicago has multiple core pieces at risk of decline over the next few years—Rose, the aging Pau Gasol and the oft-injured Joakim Noah—so the time was right to pay up to maintain momentum. There were times last season, especially before the All-Star break, when Butler had a case as the Eastern Conference's second-best all-around player, aside from LeBron James. The 2015-16 returns of Paul George, Carmelo Anthony and others will cloud that pecking order a bit, but Butler's full defensive toolbox and aggressive mentality should keep him in the All-Star discussion for the duration of this deal.

For Butler, who ranked No. 6 on's "Top 25 Free Agents of 2015" list, the financial security that this contract offers completes a remarkable personal journey. The Tomball, Texas, native was kicked out of the house by his mother while in high school and taken in by a friend's family before spending a year in junior college. Very few players land $90 million contracts in the NBA, and even fewer do so after taking such a nontraditional and delayed path to stardom. If you're looking for the biggest winners of this year's free agency, Butler is undoubtedly at or near the very top of the list. 

Grade: B