An unlikely road to Portland for undrafted free agent
From the streets of the Dominican Republic, guard Luis Montero finds way to create opportunity with Blazers.
The rookie had no driver’s license. His English was halting. All he wanted to do was go to the gym, but he had no way to get there.
The coach of the Portland Trail Blazers, Terry Stotts, had ordered a “blackout day” to encourage his players to stay away from the practice facility after too many successive practices and games. But the rookie wanted no part of resting. He could not afford to rest.
And so Luis Montero, the undrafted rookie guard of the Blazers, called one of his teammates to ask for a ride.
“I told him, ‘Hey, I want to go to the gym,”‘ said Montero, who totaled 42 minutes from the end of the Blazers’ bench last season. “So he said, ‘I’m going to pick you up from your house. I’m going to take you to the gym.”‘
The chauffeuring teammate turned out to be Damian Lillard, the star of the Blazers, who should have been more in need of a blackout day than anyone. Lillard was leading Portland in minutes, points and assists while driving his team to the playoffs last year. And yet there he was, lifting weights at the facility while Montero worked on the court. Then he bought them lunch before taking him to a clothes store to buy Montero two suits so that he could dress properly for the games. Lillard wound up spending his entire day with the rookie.
“Two suits, different colors,” Montero said. “That’s amazing. I was like, ‘Thank you.”‘
This story has been told before from Lillard’s point of view. But what does it say of Montero?
“I wasn’t the least bit surprised about Damian’s generosity,” said Blazers president Neil Olshey. “I was surprised at the complete obliviousness of Lu — that you would call the franchise player, who had played four games in five nights on the road, to give you a ride to the practice facility. Instead of calling Uber or one of my assistants that would’ve gone and picked you up, you call the franchise player to come pick you up and drive you to the gym so you can shoot? One, there are probably three or four franchise players that would have done it for him, let alone then take him to lunch and take him shopping. But the fact that Lu is so naïve and so innocent …
“Well, he likes Damian, and they have breakfast together, so: I’ll just call Damian! He’ll give me a ride! Of course, why wouldn’t he? It’s a little like the guy working on the building grounds of Google calling the CEO, going, hey, my car broke down. Can you drive me to work today? Sure. Of course. Why wouldn’t he?”
In this case, the CEO decided that the minimum-wage employee was worthy of the investment. It so happens that Lillard’s response has not been uncommon: The reason Montero is in the NBA is because many others have felt the same way.
Growing up in baseball country
In 2015 his mysterious name — Luis Montero — appeared on the long list of candidates for the NBA Draft. Steve Rosenberry, an assistant GM of the Blazers, made several calls to ask about Montero before attending his workout at Westchester Community College in suburban New York. Montero, a 6-7 guard, was skinny and out of shape. But Rosenberry saw something in him. He came down out of the stands and began to guide Montero through a series of drills. Afterward Rosenberry warned agent Billy Ceisler that Montero’s conditioning had to improve before he took on the gauntlet of pre-draft workouts with other NBA teams. And this became the first of many good signs as far as the Blazers were concerned: Within a few weeks Montero had worked himself into shape.
“He came from one of the worst neighborhoods of Santo Domingo,” said Pedro Pablo Perez, a former basketball player from the Dominican Republic who lives in New York. “From the age of 8 to 11 he was fighting on the street every day with the other kids. Then he grew up a little bit. After school he was on the basketball court until almost midnight every day. He was always playing basketball.”
Montero was a playground legend in a country with little such tradition. Every Major League Baseball team operates its own youth academy in the Dominican Republic. But there is no such infrastructure for basketball.
“Back there, everyone played basketball because they liked it – not because they want to be professional basketball players or they want to be like somebody big,” Montero said. “I think the mentality I have right now is professional, working hard every day, trying to get better every day, try to be a better player every day.”
His mentality evolved when he was discovered by Perez, who in 2011 had returned home to run one of the Dominican Republic’s professional basketball clubs.
“I saw this kid – really skinny, he was 18 – dribbling and going by people,” recalled Perez, who would bring Montero to the U.S. the following year. “I said right away, ‘This is an NBA player. What is he doing here?’ They said, ‘He’s going into the (Dominican league) draft. I said, ‘Don’t make him professional just yet. I’m going to take him to the States and he’s going to be in the NBA.”
Along the way, as Montero spent time with the Dominican national team, he would earn the backing of NBA players Al Horford and Francisco Garcia.
“Horford and those guys, they were saying, ‘This kid has a chance,” said Ron Sanchez, the associate head coach at Virginia who has served as an assistant to the national team. “He has that kind of infectious personality where people like him as a person.”
Montero’s play on the court was an expression of his personality. There was a flair to his game that was reminiscent of the great Brazilian footballers. He envisioned passes — as a playmaking ball handler and as a thieving defender — that few others could foresee. When Montero went undrafted in 2015, the Blazers signed him to their summer league team in Las Vegas and watched him make the kinds of inspiring plays that more experienced players could not imagine.
“He was a long wiry kid with ball skills who was phenomenal in the open floor, and very smooth,” said Sanchez. “Most of us are looking for guys that have this fluidity or rhythm about them, where they don’t look awkward when changing speeds and directions with the ball in their hands. I’m from New York City, and we admire those guys around Rucker Park who have that sweet game. He was just a natural basketball player that lacked fundamentals.”
Montero’s emergence in the NBA would prove not only his ability but also his ambition to learn all that he doesn’t know. His path to the league amounted to one long exaggerated stumble. A prep-school season at Wilbraham & Monson Academy in Massachusetts was followed by a freshman year of at Westchester CC. When the basketball program at Westchester was suspended before his sophomore season, Montero had nowhere to go academically. One year later, in spite of so little formal training, he found himself in the NBA.
“So many times there are these great stories about what a positive addiction can do for a kid,” Sanchez said. “Even though he didn’t have anything else, he had a ball and he had a rim. The natural love for the game can develop this love affair with it, so then somebody sees you and it changes your life. A lot of people assisted him in small ways.
“I don’t know if I would call it a miracle. It is more so the beauty of what we do. I think it’s an amazing story. It happens to Dominicans a lot in baseball. In basketball I think it becomes harder. At least in baseball they have the minor leagues where they can climb up and hang out for a while. In basketball you’re either going to make it or not.”
Life with the Portland Trail Blazers has changed the life of Dominican-born player Luis Montero (second from right), who was signed as undrafted free agent by Blazers general manager Neil Olshey (left), who also brought along other youngsters in Noah Vonleh and Cliff Alexander.
NBA life provides growth
“It’s very weird, changing somebody’s life in the NBA,” said Olshey. “We’re such mercenaries all the time. He hit a perfect situation where we were in a rebuild. He fit our model as a young, emerging talent. We thought he had some raw material that’s worth working with. But this is a kid who comes from a very difficult background. He never had three meals in a day before.”
When the NBA money started coming in last year, Montero was able to change the lives of his mother, father and 9-year-old brother in Santo Domingo.
“I guess the happiest day of his life was when moved his mom to a nice apartment in a nice neighborhood — three bedrooms, furnished,” said Perez.
“It was really important to me and my family,” said Montero. “I think everything is straight right now. It’s way, way, way better.”
He has added structure to his life, strength to his body and a wherewithal that was beyond his basketball imagination just a few years ago. “When he first came to the States he was 6-7 and 169 pounds,” said Perez. “Now he’s 6-8 and 205.”
“He came in so raw last September that it was just a real challenge,” said Stotts. “You could see the improvement he made every month, whether it was confidence, understanding the game, ball handling, shooting, playing organized basketball at this level — he was a sponge.”
And yet Montero can still be wild with the ball and unreliable while shooting from the perimeter, and those negatives may no longer be redeemable in Portland. After a highly aggressive summer, the ambitious young Blazers are approaching the new season with the most expensive payroll in the league.
“I think he’ll play for a long time, but I don’t know if it will be here or a different country,” said Sanchez. “Now he has a career. Once you have been on the NBA path, you can go elsewhere and earn a paycheck. What all of these people have done for him is to give him a fishing line rather than a fish. He can make a living and fend for himself now.”
If the Blazers realize during training camp that they can no longer afford to develop Montero, then perhaps another NBA team will be interested. Surely there will be suitors from the leagues of Europe.
“I think my future is, like, I need to keep playing basketball,” Montero said. “I need to keep getting better every day and need to keep trying to be a pro.”
“If he doesn’t play another game in the NBA and goes to Europe or whatever, he at least has some stability and pedigree now,” said Olshey. “And he’s been able to take care of his family. It’s a positive.”
This is one of those investments with all kinds of unpredictable benefits. The story of Luis Montero, wherever it may take him, is just beginning.
Ian Thomsen has covered the NBA since 2000. You can e-mail him here or follow him on Twitter.
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