The Best Rags to Riches Stories in the NBA Right Now

Kawhi Leonard knocks down a three.
Hard work has paid off for Kawhi Leonard. | Andy Lyons/Getty Images

The classic, Horatio Alger rags-to-riches story is woven deeply into American lore. Through the American Revolution, a rag-tag bunch of minutemen from a 13-colony backwater managed to fell the Mighty British Empire. Next, the likes of Andrew Carnegie and John D. Rockefeller came from humble beginnings to transform the U.S. into an economic powerhouse through the Industrial Revolution.

These days, the American dream often plays itself out in the sporting world. In the ’90s, John Starks clocked out of bagging groceries at his local supermarket to take the league by storm and throw it down over Michael Jordan. Several years later, Tom Brady, a sixth-round draft pick out of Michigan won five Super Bowls and claimed the crown as the GOAT.

There is a bit of underdog in all of us; we can all relate to feeling overlooked and under-appreciated. And these five ballplayers struck when opportunity met the blood, sweat, and tears of preparation. Now it’s time to finally cash in on all of the fame — and get paid.

5. Jonathon Simmons

Jonathon Simmons of the San Antonio Spurs drives to the basket against Kevin Durant of the Golden State Warriors.
Jonathon Simmons of the San Antonio Spurs drives to the basket against Kevin Durant of the Golden State Warriors. | Ronald Cortes/Getty Images

This offseason, swingman Jonathon Simmons signed a three-year, $18 million deal with the Orlando Magic. Four years ago, in 2013, Simmons paid $150 for a D-League tryout. This spectacular return on capital would put billionaire investor Warren Buffett to shame.

Simmons’ path to NBA stardom takes several pages out of the Kurt Warner playbook. First, Simmons attended two separate community colleges and the University of Houston. Then he forewent his senior year and declared early for the NBA Draft. The then-unknown Simmons, of course, went undrafted, with four young daughters to feed.

Jonathon Simmons of the San Antonio Spurs looks to pass.
Jonathon Simmons of the San Antonio Spurs looks to pass. | Rob Carr/Getty Images

In the American Basketball League, Simmons poured in 36 points per game through a short stint in Texas. He was on the brink of quitting before he threw his name and $150 into the D-League hat. After two more years in the D-League, the San Antonio Spurs came calling with a two-year deal in hand.

In 2015, Simmons made his NBA debut as a 26-year old rookie. By 2016–17, Simmons had firmly established himself as a cog in the Spurs’ regular rotation. He chipped in with six points per game. This postseason, Simmons dropped in 15 points per game through seven playoff starts, while a banged-up Kawhi Leonard and Tony Parker looked on from the bench. Now the local-boy-made-good will take this show on the road — to Orlando.

4. C.J. McCollum

Portland's C.J. McCollum dribbles toward the basket.
Portland’s C.J. McCollum is making a name for himself. | Christian Petersen/Getty Images

As a high school freshman, C.J. McCollum measured 5-foot-2. By his senior year, a growth spurt took the lanky kid to 6-foot-3, while weighing in at 165 pounds soaking wet. From there, McCollum played college ball at Lehigh in the Appalachian foothills. As a sign of things to come, the freshman dropped in 26 points through a close loss to top-seed Kansas in the first round of the 2010 NCAA tournament. Two years later, in 2012, McCollum lit up two-seed Duke for 30 points and closed out a shocking opening-round upset in the Big Dance.

In 2013, the Portland Trail Blazers took McCollum as the 10th overall pick in the NBA Draft. He became the first player ever drafted out of Lehigh. Then, he sat out the first six weeks of his rookie year with a broken foot, before the Trail Blazers shipped him to Idaho and the D-League. After Portland called him back up, McCollum rode the pine for two straight years, putting up a nondescript seven points per game, off 44% shooting through 2014–15.

Damian Lillard and C.J. McCollum embrace after their Game 6 victory over the Los Angeles Clippers.
Damian Lillard and C.J. McCollum embrace after their Game 6 victory over the Los Angeles Clippers. | Steve Dykes/Getty Images

That offseason, a mass exodus out of Portland had the likes of Nicolas Batum, LaMarcus Aldridge, Robin Lopez, and Wesley Matthews punching their tickets out of town. That 2015–16 season was supposed to be a rebuilding year in Portland, with McCollum sliding into the starting two-guard spot, alongside fellow mid-major alum Damian Lillard.

That year, McCollum exploded to drop in 20 points per game, en route to claiming Most Improved Player hardware. Those Blazers went 44-38 and knocked the L.A. Clippers out of the first round of the playoffs, before taking one game against the 73-9 Golden State Warriors in the Conference Semifinals.

Now, McCollum has literally come out of nowhere to emerge as one of the best pure scorers in the game. McCollum is especially good in traffic, where he feints a hard drive right to the front of the rim, before stopping on a dime and draining a mid-range jump-shot. When the defense collapses on the perimeter, a crafty McCollum will switch gears and finish in the lane, with an array of scoop and hook shots.

Last year, McCollum continued to improve across the board, in filling up the stat sheet for 23 points, four rebounds, and four assists per game. Taken together, McCollum and Lillard are arguably the best backcourt in basketball this side of Oakland and the Splash Brothers.

3. Kawhi Leonard

Kawhi Leonard drives to the basket.
Kawhi Leonard takes care of the Spurs. | Ronald Martinez/Getty Images

In 2008, Leonard’s father was gunned down in cold blood at the Compton carwash he owned. From then on, the high school senior kept his mouth shut and found solace on the basketball court. After claiming California Mr. Basketball honors, Leonard went down the 15 Freeway to make two separate NCAA Tournament runs with San Diego State. He declared for the 2011 NBA Draft as a rising junior.

On draft night, Gregg Popovich and the San Antonio Spurs pulled the trigger on a deal that shipped George Hill to the Pacers in exchange for Indiana’s 15th overall pick, Leonard. At the time, Hill was a trusted and wily veteran, fully capable of taking full command of the Spurs’ motion offense with the second unit. Alternatively, Leonard was a raw athlete and rugged defender who lacked any real semblance of a jump shot. Still, it wasn’t long in training camp before Coach Pop presented Leonard as the future face of the San Antonio Spurs.

San Antonio's LaMarcus Aldridge and Kawhi Leonard high five.
San Antonio’s LaMarcus Aldridge (L) and Kawhi Leonard play with confidence. | Thearon W. Henderson/Getty Images

By his second year in the league, Leonard was locking up against LeBron James and the Miami Heat in the 2013 NBA Finals. The Spurs were up late, three-games-to-two, before Chris Bosh chased down an offensive rebound and kicked the ball out to Ray Allen in the corner. Allen, of course, knocked down the three, swung the series, and the Heat took the 2013 NBA Finals in seven games. Leonard, for his part, put up a double-double (15 points and 11 rebounds per game) through the grueling matchup.

The following year, in 2014, the Spurs were back and ready to take what they felt was rightfully theirs. Leonard had his coming out party, dropping 18 points per game off 61% shooting from the field. On the other end of the floor, he went right at The King, harassing him into multiple turnovers and ugly shots. For this, Leonard claimed Finals MVP hardware and carried the Spurs dynasty into the post-Duncan era.

Now, it’s Leonard who rivals the great James as the best two-way player in the game. Last year, Leonard emerged as a legitimate MVP candidate, after wrecking the league for 26 points, six rebounds, four assists, and two steals per game. In Game 1 of the 2017 Conference Finals, the Spurs had the juggernaut Warriors on the ropes, up by 20 points in the third quarter, before Leonard permanently checked out of the series with an ankle injury. The Warriors immediately went on a roll — right to the NBA Finals.

2. Isaiah Thomas

Isaiah Thomas looks at the basket before a free throw.
Isaiah Thomas was once on the Sacramento Kings roster. | Mike Ehrmann/Getty Images

As the 60th and last overall pick in the 2011 NBA Draft, Isaiah Thomas was Mr. Irrelevant and heading to Sacramento. At the time, many doubted whether the 5-foot-9 athlete would even make the team, let alone transform into a star. Still, by his third year in the league, Thomas was dropping in 20 points per game.

In 2014, the dysfunctional Kings dealt IT to Phoenix for pennies on the dollars and one bag of chips. With the Suns, Thomas sat on the bench, fighting for playing time out of a stacked backcourt featuring the likes of Eric Bledsoe, Goran Dragic, and Brandon Knight. Still, IT cobbled together an average of 15 points through 25 minutes per game of action in the Valley of the Sun. That February, Phoenix sent Thomas to Boston in exchange for Marcus Thornton and a pick.

Isaiah Thomas is pumped up after making a three.
The Celtics have a true closer in Isaiah Thomas | Maddie Meyer/Getty Images

Thomas finally found a home as the heart and soul of the Boston Celtics. Last year, he transitioned from Mr. Irrelevant to Mr. Fourth Quarter as he tallied 29 points per game. Scrappy Thomas would take control down the stretch, late in the game to attack the rim. After forcing the defense to commit, Thomas would casually step back behind the arc to drain a wide-open three ball. These Boston Celtics, largely because of Thomas went 53-29, to close out the regular season as the No. 1 seed in the Eastern Conference.

Right before the 2017 NBA Playoffs, his sister, Chyna, died in a tragic car crash in Tacoma, Washington. Still, Thomas pulled himself together and dropped 33 points on the Chicago Bulls the very next day. From there, the Celtics marched through the playoffs before running into James and a brick wall in the Conference Finals. In response, Danny Ainge worked the phones this offseason to reload with third overall pick Jason Tatum and free-agent prize Gordon Hayward. Boston is back, with lead guard Thomas in the catbird seat.

1. Jimmy Butler

Jimmy Butler shoots a free throw.
Jimmy Butler shoots a free throw. | Jonathan Daniel/Getty Images

In grade school, Jimmy Butler’s own mother kicked him out of the house. From there, he crashed at the homes of friends for weeks at a time, until he found himself shooting baskets in an empty gym with future NFL pickup Jordan Leslie. Shortly thereafter, Butler started living at the Leslie family home. Throughout this turmoil, the game of basketball remained a constant in his life.

After staving off homelessness, Butler put in a one-year stint at Tyler Junior College before ultimately landing at Marquette. By his senior year at Marquette, he was dropping in 16 points per game. In 2011, the Bulls selected Butler as the 30th overall pick in the draft. As a rookie, he could barely get off the bench, good for a nondescript three points per game.

Jimmy Butler puts up a shot at the rim.
Jimmy Butler has a new home in Minnesota. | Jonathan Daniel/Getty Images

Like always, Butler gradually developed from a bench warmer to an energy guy to a bona-fide superstar. Early in his career, he flanked Derrick Rose as an attack dog and fierce on-the-ball defender. With time, however, Butler perfected his jump shot and wrested control of this team away from D. Rose, who ultimately packed his bags for New York City. Last year, Butler racked up 24 points, six rebounds, and six assists per game.

This offseason, Butler found himself as collateral damage to the ongoing rebuild in Chicago. The short-lived “Three Alpha” era that featured Butler, Dwyane Wade, and Rajon Rondo has already blown up, so that John Paxson and Gar Forman can stockpile draft picks and cap space in the front office. To kick off the rebuild, Tom Thibodeau and the Minnesota Timberwolves packaged Zach LaVine, Kris Dunn, and seventh overall pick Lauri Markkanen in exchange for Butler.

Now, the T-Wolves are one of the more intriguing teams in the league, after matching Andrew Wiggins and Karl-Anthony Towns up with Butler and Taj Gibson. Certainly, the old Bulls will mentor the young guns on the intricacies of the Thibodeau defense. Expect Butler to lead this squad into the Western Conference playoffs, where they will emerge as a tough out for the Golden State juggernaut. This is the ultimate rags-to-riches story — for a man set to collect $17.5 million in base salary this season.

Statistics courtesy of ESPN and Pro-Basketball-Reference.