Now, mainly due to a lack of information, the value of the 21-year-old left-hander has reportedly dropped, from the $60 million over six years that had been floating around to something resembling the four-year, $15.1 million Stephen Strasburg signed for with the Nationals this summer.
But whether Chapman gets $60 million or $15 million, his journey from the kid who has nothing to the one some may eventually say has too much should be completed at some point this offseason.
And Tuesday could be Judgment Day.
According to ESPN.com, Chapman's much-anticipated side session in front of Major League teams is expected to happen that day in Houston, with the Red Sox, Yankees, Angels and a host of teams attending in hopes of acquiring some answers on the Cuban defector who's been nothing short of an enigma thus far.
"We need to see him throw before we start getting extremely involved in that," said Angels general manager Tony Reagins, echoing the sentiments of many front-office members around the Majors. "The dollars are going to be significant."
It was about two years ago that Chapman put his lanky, 6-foot-4 frame on the map with his triple-digit fastball. Now, months after escaping poverty in Cuba and despite the perceptions of a shrinking market, he stands to land a big-money contract from one of the several teams willing to sacrifice the unknown for the potentially historic.
Chapman's transition from nothing to everything will help smooth the way as he adapts to his new country, but it won't be easy -- not when his entire livelihood depends on trying to master a game he's still far from perfecting.
Focus tends to waver when your forms of entertainment shift from your friend's beat-up bicycle to iPhones, PlayStation 3s, luxury cars and all the other material objects that come with money.
And Chapman's focus will be tested.
"When you get to the U.S., you're given a certain amount of money, but that can't change the person you are," Vladimir Nunez, a nine-year Major League veteran who also defected from Cuba, said. "It can't stop you from striving to achieve your dreams. You have to remember that you came here for an objective -- to play baseball and try to make your dreams a reality."
For Chapman, the first step in making his dreams a reality was relatively simple.
Finding the 'Exit' sign
After being caught and reprimanded in 2008, Chapman kept his second plans for defection a secret -- even from his immediate family -- until he walked out of his hotel room in Rotterdam, Netherlands, while playing in the obscure World Port Tournament in July. He got in a car driven by an acquaintance and ended up in Andorra, where Major League Baseball eventually granted him free-agent status.
But for so many others, the path from Cuba to the U.S. was a lot more difficult.
Juan Miranda was one of more than 15 people who squeezed into an average-sized fishing boat about five years ago and spent five days in uneasy waters, eating little, frequently succumbing to seasickness and wondering if he'd make it out alive.
"Imagine, you're putting your life on the line," Miranda, a 26-year-old first-base prospect for the Yankees who saw action in eight Major League games in '09, said. "Being in the water, anything can happen there."
Miranda, as did Chapman and Nunez, left his entire family behind for the chance to go from earning less than $15 a month as a pro baseball player in Cuba to making millions playing in The Show.
But many have been unable to find that path recently.
Cubans lacking in the Majors
When Hall of Famer Tony Perez came to the U.S. in the early 1960s, pretty much all it took to play in the Major Leagues was a visa, a plane ticket and a signature on a contract. Perez wasn't exactly forced to leave his family behind -- though they decided to stay -- or put his life on the line as part of an intricate defection plot.
In 1960, when Fidel Castro had only been in power for one year, there were 22 active Cuban-born players among 16 teams in the big leagues.
But in 2009 -- because of tight restrictions and Castro's ideologies -- only 13 players born in Cuba saw action among 30 Major League teams. Comparatively, from other countries that hold baseball in as high esteem as Cuba, there were 128 from the Dominican Republic, 87 from Venezuela and 36 from Puerto Rico this past season.
"It's disappointing to all of us [from Cuba], because we want those kids to get out and be able to play in the big leagues," Perez said. "But when the government changed over there, and we had to get out and stay back here, we just knew there wouldn't be too many coming out."
The task of defecting from Cuba started with Rene Arocha, who left the country in 1990, then went on to go 18-17 with a 4.11 ERA in four seasons in the Majors.
No defector made more money than Jose Contreras, who signed a four-year, $32 million contract with the Yankees in 2002 -- some believed Chapman could top that figure, but that seems questionable at the moment -- and nobody seemed to initially handle the process as smoothly as Livan Hernandez.
Hernandez left Cuba at just 20 years old in 1995, and two years later he was named World Series Most Valuable Player after a fantastic rookie season with the Marlins.
But though Livan Hernandez; his half-brother, Orlando Hernandez; and Contreras have had success in the big leagues, and such position players as Yunel Escobar, Kendry Morales and Alexei Ramirez are starring for their respective teams, Cuban pitchers haven't really stood out in the U.S. recently.
Perhaps Chapman can break that trend.
"I want to be the best pitcher in the world," Chapman told ESPN.com in late October. "I'm not yet. But with work I can be."
From rags to potential riches
Chapman's star was born during the 2007 World Cup, when he struck out 20 batters in 15 innings over two dominating starts.
He tried to defect in the spring of 2008. And though his plan was foiled by Cuban authorities, a meeting with President Raul Castro resulted in Chapman catching a break, as he was suspended for the remainder of the National Series season but would eventually be able to pitch in the 2009 World Baseball Classic.
After a subpar performance in the Classic, Chapman successfully defected during the summer, leaving behind his parents, two sisters, his girlfriend of two years and a newborn daughter he still hasn't seen.
He spent his first four days of freedom in Amsterdam, where he met with his first agent -- Edwin Mejia -- then drove through France to get to Barcelona and establish residency in the tiny nation of Andorra.
He then came to the U.S., appearing in Yankee Stadium to watch Game 6 of the American League Championship Series and meeting with various GMs, some of whom question his character, demeanor and maturity level.
Then, on Nov. 21, it was reported that Chapman had dropped Mejia's agency, Athletes Premier International, and signed with the more experienced Randy and Alan Hendricks.
Since then, Chapman has been sheltered from the media. His new agency refused several interview requests from MLB.com, and it's evident they don't want the national attention that has engulfed Chapman to distract him from inking his first Major League contract.
The Yankees, Red Sox, Angels, Orioles and Tigers have shown interest, and the Royals and Phillies have him on their radar. But to what extent are those teams willing to commit a significant portion of their payroll for a prospect whose negatives are just as evident as his astonishing positives?
A success story?
On the one side, there's the fact that Chapman -- along with Japanese pitcher Yu Darvish -- is one of the best players in the world not in the Major Leagues, that the free-agent pool for starting pitchers is weak this year, and that the list of southpaws who throw 100 mph is short -- Billy Wagner, Randy Johnson and Steve Dalkowski.
But then there's his perceived lack of command of a secondary pitch, recent subpar numbers while facing inferior competition in Cuba, frequent problems finding the strike zone and, most important, the fact most teams have barely seen him pitch first-hand, if at all.
"When you invest in a young player, you never know what you are really getting," said Andres Reiner, the Rays' special assistant of baseball operations, who deals mainly with Latin American players. "You know a lot better when he's coming from college than when he's coming from the Dominican or Venezuela or Cuba.
"You don't know if [Chapman] will survive or not."
Through four seasons in the National Series -- Cuba's professional league -- Chapman went 24-21 with a 3.72 ERA, 379 strikeouts and 210 walks in 341 2/3 innings. But last year he had a subpar 4.03 ERA in 118 1/3 innings.
No team has reportedly made an offer yet.
"If you're spending somebody else's money, and a lot of it," Nationals assistant GM Bob Boone said, "you better do your homework."
One thing is almost certain: Considering his raw ability and the amount of things coming at him so fast, Chapman will need time to develop.
"He has tremendous ability, a tremendous arm, and he's a very young kid, so he has all the future ahead of him," said Cookie Rojas, a native Cuban and former 16-year Major Leaguer who's now a Spanish-radio broadcaster for the Marlins.
"But it's going to take him a while to show what kind of ability he has, how he can adjust and how he can get with his teammates."
Alden Gonzalez is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.