How Reche Caldwell Googled his way from the Patriots to prison

How Reche Caldwell ended up in prison (3:35)

ESPN senior writer David Fleming joins the Dan Le Batard Show to detail how former NFL wide receiver Reche Caldwell googled his way to prison. (3:35)

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THE FIRST LESSON Reche Caldwell learned in prison is that no one escapes on a Tuesday. Here in Montgomery, Alabama, Tuesday is movie night, and anyone who went on the lam last week, for instance, would have missed Morgan Freeman's timeless tour de force Lean on Me. Caldwell, the leading receiver on the 2006 Patriots, might be the most inept criminal the NFL has ever produced, but give him credit for this: He was clever enough to get locked up at FPC Montgomery, a waterfront minimum security prison "fenced" inside the Maxwell Air Force Base by nothing more than a row of meticulously manicured crimson crepe myrtles. For inmates, the only real threat of bodily harm comes from the tee box of the Cypress Tree par 5 that runs down the length of the camp's west side. For visitors, the only disconcerting moment is at the security entrance, checking in while prisoners stroll past unfettered and headed toward the shimmering waters of Gun Island Chute, or perhaps the equestrian stables just across the road.

Caldwell arrived here at the beginning of 2015 after an epic crime spree that was eerily similar to his NFL career -- short-lived, unfocused and full of colossal blunders. His 10-month rager included two SWAT raids, four arrests, a half-eaten hoagie (we'll explain) and Maxwell House coffee tins stuffed with cash. He also faced a litany of charges for running a multimillion-dollar gambling house in West Tampa and then, after that operation got busted, attempting to import and distribute what he thought was more than 5½ pounds of pure Molly (MDMA).

Sentenced to 27 months in Montgomery, Caldwell went the first year without any visitors. But on the eve of Super Bowl 50, a game that featured his little brother, then-Broncos wideout Andre Caldwell, Reche crosses the prison (court)yard unescorted and enters the visiting area right on time. He looks well-fed and relaxed, his eyes calm and bright. Gone is the gaunt, bug-eyed visage from his mug shot and the disastrous 2006 AFC championship game with the Patriots.

He's dressed in standard military-issue forest green slacks and a matching short-sleeved shirt over a khaki brown T-shirt, sporting a shiny black watch, immaculate, untied Timberlands and just a hint of a supplicant's smile. He's got the thick neck and meaty forearms of a con who pumps iron twice a day, every day. For the first time, Caldwell has agreed to speak about his crimes and the Forrest Gump-like football life that led up to them. But when he sits down and begins to nervously pick at the faux wood laminate on the desk in front of him, the physical manifestations of his wild ride come into focus -- the premature specks of gray that dot the thinning hair on the crown of his head.

His head stays bowed like that for a long time, until he's asked to explain exactly how he went from the Patriots to prison, how he transitioned from being the best receiver in New England to the worst drug kingpin in Tampa. Finally, Caldwell lifts his head and a wry smile unfurls across his face. That's easy, he roars.

"I Googled it, baby!"

IT ALL STARTED with Caldwell flat on his back inside the Buccaneers' stadium in Tampa, staring into the sun.

At age 8, Reche (pronounced: REE-shay) brought home his first athletic permission slip. "I asked my husband, 'Do you think he can do it?'" recalls Reche's mother, Deborah Caldwell, who has worked with the Florida Department of Juvenile Justice for 26 years. "Ever since then, we have been a sports family." With rare speed and the preternatural chill that is shared by the greats but often mistaken for aloofness, Reche developed into the best all-around athlete Jefferson High in West Tampa ever produced. And so in 1997, as a prep All-America quarterback and a soon-to-be draft pick of the Cincinnati Reds, he had a decision to make. Stretching before a high school showcase game inside the stadium, he closed his eyes and, as the sun warmed his face, realized his dream was to return to this field one day as an NFL player. The choice set Caldwell on an accidental odyssey through the highest levels of football, torturously close but always on the periphery of some of the biggest names and greatest games in the sport.

Caldwell attended Florida, where, after converting to wideout, he starred in the final incarnation of Steve Spurrier's Fun 'n' Gun offense. That led to the 2002 NFL draft, in which the Chargers selected him in the second round using a pick from a 2001 trade that sent the No. 1 choice to the Falcons, who selected Michael Vick. After four seasons in San Diego plagued by injuries, undisciplined routes and wildly inconsistent hands, Caldwell signed with New England, where at midseason -- and to his great surprise -- he was elevated to Tom Brady's primary target after Deion Branch was dealt to Seattle. The plan worked fine, at first. Caldwell led the team's patchwork receiving corps with 61 catches for 760 yards and four TDs in the regular season. In the divisional playoffs in San Diego, he recovered a fumbled interception late in the fourth quarter and, five plays later, hauled in a TD pass that led to a 24-21 win. "No one remembers that game," he says. "Only the next."

The next week, in the third quarter of the AFC championship game in Indianapolis, a perfectly placed go-ahead touchdown throw from Brady bounced violently off Caldwell's outstretched hands in the back corner of the end zone. Then, in the fourth, on first-and-15 at the Colts' 18, with the score tied at 24, Caldwell trotted away from the huddle and took a wide split, almost to the Patriots' sideline, when he realized there wasn't a defender within 12 yards. After the snap, Caldwell slid downfield, waving his arms at Brady, who again delivered the ball right on target. But when Caldwell pivoted upfield with nothing but grass between himself and the Super Bowl, his momentum caused the ball to squirt out of his grasp and flutter down to the turf.

As he walked back to the huddle in a daze, commentators roared in disbelief while network cameras zoomed in. Caldwell appeared to be channeling Gollum, repeatedly bulging his eyeballs as if trying to violently pop his pupils -- and the vision of that costly drop -- out of his skull like two champagne corks. The image stuck with the Patriots for more than a year, but it has haunted Caldwell for the better part of a decade. "He heard all the jokes and criticisms," says Andre, who is now with the Lions. "And it broke his heart."

New England dumped Caldwell after the season and rebuilt around Randy Moss. Teammates turned on him as well, whispering that he was "allergic to work." The next season, Caldwell played in Washington, where he fulfilled his dream of returning to play the Bucs at home, but he accomplished little else. He lasted through training camp with the 2008 Rams but in the end couldn't escape his Indy indiscretions. It stained his rep as a free agent and eroded his confidence and his love of the game.

Hardly a week goes by, still, when Caldwell isn't reminded of a single dropped pass that has come to define 20 years of his life. When he met with law enforcement after his Molly arrest, Caldwell recognized the FBI agent's Boston accent and sat back and waited. "You're that guy who cost Tommy anudda Soupa Bowl," he howled. Caldwell bit his tongue. "What else can I do?" he says. "It's not like I was trying to drop those passes." But Andre is convinced that what happened in Indy tortured and then transformed Reche. "The way the game kicked him to the curb like an unwanted stepchild hurt him mentally and haunted him," Andre says. "Reche got a little bit of a selfish attitude out of it, like, 'Forget everybody else, I'm gonna start worrying about me.'"

USING HIS NFL money, including the $1 million he received for his 15-catch contribution to the 2007 Washington team, Reche helped relocate his family to a gated community near Cory Lake on the northeast side of Tampa. Just a semester shy of a degree in leisure services management, Caldwell had opened a short-lived event planning company, Adore and Decor, in 2005. He trained a few athletes, worked as a volunteer coach and thought about opening a car lot. But nothing came close to filling the football-shaped hole in his life. "Reche was ill-equipped to handle life outside the NFL," says his attorney, Nicholas Matassini. "He was jobless, he was bored, he had a bunch of money, and he didn't know what to do with himself."

By early 2013, his grandfather was sick, his marriage had begun to disintegrate and his kid brother had finally surpassed him on the football field. A restless Reche, family members say, started making a daily 45-minute commute from the suburbs to his old West Tampa haunt, 10 blocks from downtown and 10 years back in time. He might have been a laughingstock in the NFL, but in West Tampa, Reche was still royalty.

Most days he hung out in a tiny, dilapidated brick building tucked in the shadow of I-275 between a boarded-up factory and an empty, overgrown lot. A barbershop occupies the east end of the building, and a car-detailing business, a billiards room and a storefront area, featuring three ticket windows, fill the other side. Police say with Caldwell's bankroll and the help of several associates, the corner transformed into a wildly popular homegrown gambling parlor. And Caldwell didn't keep a low profile -- his bright red Jeep parked out front was like a neon OTB sign. He says he liked to gamble, especially on football. But what he really loved was feeling as if his experience and expertise about the game were back in high demand. "He was just a happy-go-lucky guy who liked to smoke pot, gamble, hang out and talk about sports," Matassini says, "and that's it."

Speaking from prison, the most animated Caldwell gets is when talking about gathering around his parlor's makeshift bank of TVs to watch the end of seemingly meaningless games, like Northern Illinois -- Ball State in 2013. Ball State had the ball with 46 seconds left to play and NIU leading 41-27. Caldwell was silently celebrating because he had failed to control just how much money was placed on the 72.5-point over. But then the Huskies' Joe Windsor picked off a pass at midfield and returned it all the way for six. The tiny space exploded in celebration, bills fluttering like ticker tape, everybody chest-bumping and high-stepping out into the street, and Caldwell was right there with them. He couldn't have cared less about the money. "It was about the excitement and the connection to football," he says. "Is that what I missed? Is that what I was trying to make up for? Maybe so. We did well, and it kept me busy. I enjoyed it. Probably too much."

Before long, Caldwell was doing almost $225,000 in wagers each month. He didn't like banks, so cash would be crammed into Maxwell House coffee tins and piled up everywhere, in the microwave and in crooked, Dr. Seuss -- like stacks that stretched to the ceiling. What had been a sleepy little mom-and-pop car-detailing shop was overrun by as many as 40 cars and nonstop foot traffic from Friday through Monday -- changes that were hard to conceal, seeing as how there was an elementary school across the street. "I see now, yup, not the greatest location for that kind of thing," Caldwell says with a chuckle. "Too big, too fast. I laugh at my stuff too. What else can you do? I have to laugh. I really thought I was some kind of a criminal? All I know is, everyone kept telling me, 'The police don't care about this stuff, you'll never get caught,' and the next thing I know I'm headed to prison, saying goodbye to my kids, wondering: 'What happened to me?'"

The NFL was curious as well, according to Matassini. Off-book gambling was a low priority with the Tampa police, he says, until NFL security asked them to look into rumors of former players involved in illegal gambling rings. The NFL declined to comment, and the Tampa police don't recall the investigation starting that way, but by November 2013, Caldwell's customer base included several undercover informants. Then on wild-card weekend in early 2014, Caldwell was at a desk in the secured back office of the betting parlor, enjoying a late-afternoon snack while watching his old team, the Chargers, dominate the Bengals. Caldwell was so oblivious to any threat from law enforcement that when the first police flash grenade shook the building, he took another few bites of his sandwich and turned up the volume on the game. "Then -- boom -- another one went off," he says, "so I get up and walk out, and there's like 50 police and tanks ramming the door and guys screaming and swarming in from everywhere, helicopters and sirens and smoke, total chaos, and it's still not registering."

Unaware and a bit annoyed, he says, Caldwell walked right into the haze, coughing and waving the smoke away from his face. Swarmed by SWAT members, on his way to the ground, a still exasperated Caldwell yelled, "Damn, man, you blasted the door with a tank? Why didn't ya just knock? I woulda let y'all in."

ARRESTED AND CHARGED with bookmaking and running a gambling house, Caldwell posted a $4,000 bond the next morning and was back out partying with his crew. While spending time in Tampa-area clubs, Caldwell noticed a demand for the energy- and sensory-boosting party drug MDMA, aka Molly/Ecstasy. "People were constantly asking me if I knew where to get it," he says.

Had he acted immediately on his hunch, Caldwell would have remained on the right side of the law, at least initially. In March 2014, a synthetic type of MDMA, ethylone, was still legal in Florida. But by early May, when Caldwell finally got around to doing some research on his girlfriend's computer, the DEA had made the drug illegal, and MDMA confiscations by U.S. Customs had risen 1,335 percent since 2008. Caldwell says that on May 8 he simply opened up Google, typed in MDMA-Molly-China and watched as dozens of websites popped up offering to sell the drug and ship it right to his front door. (Challenged on this, Caldwell says, "You got your phone on you? Try it. It's easy." He is, in fact, correct.) Caldwell did the math: An investment of less than $2,000 could net as much as $180,000 on the street. Three taps of the mouse, a trip to Western Union and "the stuff was on its way," he says. "So easy and out in the open, I kinda did it just to see if it was a scam."

According to a police affidavit, five days later, a Tampa postal inspector flagged the package, noting it contained 4.8 pounds of a "white rocky substance." When it tested positive for MDMA, a federal agent, posing as a UPS employee, drove the drugs to the home of Caldwell's girlfriend, located in an upscale, gated condominium complex north of Tampa and directly across from the entrance to Busch Gardens.

Caldwell answered the door and quickly scanned the yard, street and air searching for trouble. Sensing none, he drew an X on the signature pad and reached for the box. Caldwell remembers the agent drew back, then improvised: "With international deliveries, I need a verifiable signature or I can't release the package." Caldwell glanced back over his shoulder at his phone sitting on a hallway table, realizing at that moment that using an app to obsessively track this package, along with another kilo he had forwarded to Atlanta, probably wasn't the smartest idea. If this is it, he thought, they already got me. Caldwell shrugged, waved for the clipboard and gave what turned out to be his last high-profile signature.

The courtyard exploded like a confetti cannon, with dozens of agents and officers materializing from behind every bush, doorway and corner that Caldwell's acute criminal instincts had deemed clear just 10 seconds before. Familiar by now with SWAT team procedures, Caldwell dutifully lowered himself face-first onto the stone porch stoop as one thought ran through his head: "Aw, man, not again."

TO THIS DAY, Caldwell isn't sure how authorities took down his drug cartel so swiftly. Perhaps it was the poorly stuffed shoebox-sized package wrapped in elaborate Chinese markings that sounded like a Molly-stuffed maraca moving down the post office's conveyor belt. "Good lord that boy was a bad criminal," says his mom, "and thank Jesus for that."

Some of those hosannas should be directed at his defense attorney. "He had been caught red-handed," Matassini says, "and by that I mean the drugs were literally found, by police, in the hands of my client, who was also tracking them on his phone." So Matassini persuaded Caldwell to take responsibility (without cooperating with law enforcement) and score points by saving the U.S. Attorney the trouble of having to prosecute the case.

All he had to do was stay out of trouble until sentencing. (Except for a misdemeanor battery charge in 2009, Caldwell had never had run-ins with the law.) But by this point, staying out of trouble was proving difficult. Twice in August 2014, Caldwell was pulled over and charged with several traffic violations and possession of cannabis. He was convinced his NFL pedigree made him an irresistible trophy for police. (On the affidavit for his drug arrest, under Business Address, the officer seemed to gleefully inscribe: "Retired.") But maybe, as Matassini suggested, Caldwell just needed to stop driving erratically late at night in a bright red Jeep that reeked of pot. The traffic stops were more of a concern to Matassini than the gambling charges, which he considered "sort of a joke." The discovery in that case was so voluminous -- and the penalties so inconsequential -- that when the prosecutor realized the amount of work needed to bring the case to a speedy trial, she let Caldwell off with time served.

Caldwell's dumb luck continued that fall in federal court when Matassini was able to, once again, turn his client's criminal naïveté into his best defense. Testing of the drug packages revealed that, as a newbie drug dealer, Caldwell was less Tony Montana and more Saul Silver. Distribution of pure Molly carries a maximum 20-year sentence and up to $1 million in fines. Instead, Caldwell ordered ethylone, what he thought was low-grade "legal Molly," from the Chinese website. Of course, it was neither. Matassini was then able to prove, with the expert testimony of a chemist, that on a molecular level Caldwell's bargain-bin drugs were a far less potent form of MDMA and therefore should fall under more lenient sentencing guidelines.

U.S. District Judge Virginia Covington agreed. After waiving all fines, she delivered a sentence of just 27 months to Caldwell, who left the court in shackles and a smile, overwhelmed by the strangest feeling: relief. In over his head in West Tampa, things had spun so wildly out of control that, Caldwell says, he genuinely felt lucky to make a clean break and restart his life after only 27 months.

"I've never seen a guy so happy to go to prison," Matassini says. "He just wanted to get the hell out of Dodge and have this all behind him."

AT FPC MONTGOMERY, the only tough stretch for Caldwell is experiencing his baby brother's Super Bowl triumph from afar. As Reche recounts his crime spree, Andre flies the entire family to San Francisco for the Super Bowl, and on friends and family day for the players, he even gets Peyton Manning to pose for a picture with Reche's son, Cash, who has dyed his hair orange. Monday morning after Denver's victory, Andre's phone rings in the team hotel: This is the federal prison camp in Montgomery, Alabama, you have a call from inmate ... YOU GOT THAT RING, BUBBA! ... press 1 now to be connected. Spurned by the sport he loves, Reche tries to feign indifference when it comes to football. But on the phone with his brother, he confesses that it has always been his dream to win a Super Bowl. "Now I'm so proud to be the one living through you," he tells Andre.

This month, Caldwell will be eligible for a transfer to a Tampa-based work-release facility, where he's looking forward to taking Cash fishing and watching his daughter graduate, with honors, from high school before heading off to college. His plan is to manage a family property in West Tampa, work as an athletic trainer or open that car lot. Facing three years of court-ordered probation, Caldwell understands that his future now rests in the most frightening place of all -- his own hands. "I'm not gonna blame football or concussions like everybody else for my mistakes," he says. "I don't blame my education or my hometown or my family. I have a great family. I had a great childhood. I grew up in a great place. This is about losing my way, being around bad people and making bad choices, and that's all on me."

Caldwell falls silent and bows his head, letting his mea culpa hang in the air. When he looks up again, there's someone standing behind the glass door. Caldwell nods. A prison employee in a black leather coat steps inside and taps on his watch. After exactly 120 minutes, Caldwell's time is up. Perhaps FPC Montgomery is a bit more strict than it first appeared.

Nah, says the guard. At 3 p.m. they need this space for aerobics class.