Esteban Loaiza's Wrong Turn

The two-time MLB All-Star had it all: A career worth millions, the love of a country and a marriage to an international music sensation. So how did he end up broke and in federal prison?
photo of Scott MillerScott Miller@@ScottMillerBblNational MLB ColumnistMay 28, 2020

Fireworks blasted and fans roared as Esteban Loaiza trotted onto the field along with the rest of the American League All-Stars to begin the biggest night of his life. It was a gorgeous summer evening, July 15, 2003. As he warmed up on the mound, looking resplendent in the home pinstripes of the Chicago White Sox, 47,609 fans stuffing U.S. Cellular Field showered him with adoration.

"Esteban Loaiza ... I guarantee you he's never had an ovation that sounded like that," Joe Buck said on a Fox telecast that was being beamed to 200 countries before Loaiza fired a first-pitch strike to St. Louis' Edgar Renteria.

One of those countries was Mexico, where Loaiza was born, in Tijuana, on New Year's Eve 1971. He grew up like so many in the area, straddling the border with one foot in Tijuana and the other in San Diego. So did childhood buddy Jose Silva, who met Loaiza when he was nine (Loaiza was 11) before they grew to pitch for rival San Diego-area high schools and later, serendipitously, became teammates with the Pittsburgh Pirates in 1997 and 1998.

"We were good friends," Silva says. "Fun guy."

It had been a long and bumpy road to this moment, and not only was Loaiza now on center stage in Chicago but in the entirety of Mexico as well. By summer's end, he tied Fernando Valenzuela for most victories in a season by a pitcher born there with 21. When Loaiza pitched, a nation beamed.

More journeyman than ace, Loaiza was persistent—and different. Once in Texas a few years earlier, word got back to his Rangers teammates that he was out in the players' parking lot washing his car—in the middle of a game, in full uniform. Oh, how he loved his cars—sports cars, fast cars, sleek cars. Luxury watches and clothes, too. He enjoyed every bit of The Show, and the perks that came with the paychecks.

Now, he had harnessed a cut fastball and immense pride and funneled them into the season of his life. In the stands at that All-Star Game were his girlfriend Ashley, their son Sage (then two), his parents Luis and Maria, his sister Maria Luisa and brother Sabino and several cousins.

"I just want to say I'm really happy to be here," a proud Loaiza said at a press conference the day before, adding, "I've always had the talent, and I've proven now this year, and I just want to keep on doing it."

For several years, to varying degrees, he did.

And then he crossed the border one final time.

He was traveling in the far right lane, according to federal prosecutors familiar with the case, in his Mercedes-Benz SUV with his turn signal blinking as he approached a Home Depot in Imperial Beach, a community in southwest San Diego County located roughly six miles north of the Mexican border. Instead of turning on this February day in 2018, at the last instant he continued straight. The decision nearly caused a collision with the car to his left.

When he did turn into the next parking lot, so, too, did the sheriff's detectives who had been tailing him. Unbeknownst to him, Loaiza had been under surveillance for some time in a federal narcotics investigation.

Detectives deployed a narcotics dog to sniff out a secret, after-market compartment in the trunk designed to transport drugs. Though it was empty, attached to a garage door opener inside the vehicle was a sticky note with an address to a nearby townhouse. Parked adjacent to the space that Loaiza pulled his Mercedes into was a 2005 Hummer that recently had been observed crossing the border. Inside that vehicle was another garage door opener with the same address attached—plus a backpack with Loaiza's name stitched across it that contained numerous bank documents.

Authorities then obtained a search warrant, and the investigation led back to the townhouse, where inside the garage was a Nissan Quest minivan that contained some 44 pounds of cocaine—estimated street value: $500,000—hidden in the rear floor panels underneath some strewn baseball bags. The townhome itself was empty, devoid of furnishings or belongings.

Esteban Loaiza soon found himself in custody after law enforcement officials searched this garage and townhouse where Loaiza was headed one day in 2018 and found 44 pounds of cocaine.
Esteban Loaiza soon found himself in custody after law enforcement officials searched this garage and townhouse where Loaiza was headed one day in 2018 and found 44 pounds of cocaine.Scott Miller

Loaiza pleaded guilty to felony cocaine possession with the intent to distribute and was sentenced to three years in prison. Because he was a resident but not a citizen of the United States, the judge also ruled that upon his release, he would be deported to Mexico. At Loaiza's sentencing, the prosecutor said the former pitcher claimed he was broke after making $44 million in his baseball career. Loaiza told the court he had four cars and zero properties.

Across the game, ex-teammates, rivals, executives and fans were stunned: How does a man's path take him from the top of the baseball world one summer evening to a deserted stash house and the wrong side of the law almost 15 years later?

The man once lifted by a roaring ovation in the Midsummer Classic now wears No. 68072-298 in the Seattle-Tacoma Federal Detention Center.

Location had been everything for Loaiza. He didn't have overpowering stuff, but he had an uncanny knack for pumping strikes. He wasn't a perennial All-Star, but he held enough potential and talent that he pitched for eight different clubs in a 14-year career.

The Pirates signed Loaiza in 1991 through a working agreement with the Mexico City Red Devils. He made the team's Opening Day roster in 1995 and started 87 games over the next three-and-a-half seasons.

When the Pirates added Silva in a deal with Toronto after the 1996 season, the former high school rivals were thrilled.

"Awesome," Silva says. "You can't ask for any better than that, knowing someone on the team you grew up with. Old friends know you, they tell you what you're doing right, what you're doing wrong. He had been in the league a few years, and I was just coming up. You're a rookie trying to learn where to go, who to be with. He helped me out with where to live. Not too many guys do that."

Adds then-Pirates general manager Cam Bonifay: "The young Mexican players stuck together because they were in Pittsburgh, of all places—the early-season weather, getting adjusted to life in the U.S. Esteban, of course, was from the border, so he spoke English, he was bilingual, and that was a big help to the kids who came over."

To those who knew Loaiza, especially in the days when he was gaining a foothold in the game, he was a special kid with a big heart—maybe too big in some cases. Through the years, Loaiza—who declined an interview request for this story through the FDC SeaTac—purchased homes for his parents, brother, sister and at least one cousin. He furnished them with automobiles. Extended family members came with their hands, well, extended. He was both generous and naive, a dangerous combination, especially in a high-pressure game in which big salaries can be blood in the water for self-indulgent hangers-on and scam-artist sharks.

You're a rookie trying to learn where to go, who to be with. [Loaiza] helped me out with where to live. Not too many guys do that.
— Loaiza's former Pirates teammate, and fellow Mexican, Jose Silva

"His family kept drawing and drawing and drawing from him," one person close with the Loaizas says.

The feeling among some of those close to the pitcher, the person says, was: OK, if your brother needs a car, fine. But it doesn't have to be a luxury vehicle. Family can be a source of anxiety often overlooked by those outside a player's inner circle, and it is especially endemic to athletes in all sports who have experienced poverty growing up.

"That's what people don't understand," says Silva, who in retirement offers private instruction for young players and works with travel baseball teams in the San Diego area. "You have all of those millions, and now Uncle Sam takes this part, then there's this and that, and then you want to help your parents out, your family. I tell guys, 'You know what, hopefully your family is awesome, but [keep it] to your immediate family.'

"You can't support everyone, dude. If you had a rich uncle, would he take care of you?"

Several attempts by B/R to interview Loaiza's siblings were rebuffed. "Right now, the family just wants to stay to ourselves," his sister, Maria Luisa, says.

On the field, Loaiza, then 26, helped the Rangers win the American League West title in 1998 and then again in 1999.

Off the field, his life was tilting toward the tabloids.

He had begun an affair with Ashley Esposito, then 19, who nannied for teammate Ivan Rodriguez's family. Of the many issues surrounding the relationship, there was this: Loaiza had married a woman named Christina Teadora Varrasso back in Pittsburgh in October 1998, just three months after the Pirates had traded him to Texas.

According to documents from the Texas Second District Court of Appeals finalizing the divorce of Loaiza and Varrasso in October 2004, the affair started two weeks before Loaiza and Varrasso were married.

"I'm not going to say it wasn't whispered, 'What the heck is going on here?' but once it came to light, they didn't hide it," a Rangers teammate who requested anonymity says. "To be honest, if you're a player and you're worried about that, you've got bigger issues than whether you can hit a 3-1 fastball."

Rodriguez says he was not surprised when Esteban and Ashley started dating, nor did he have a problem with it.

"Destiny is meant to be," the Hall of Fame catcher tells B/R. "They got together, they lived together, they had a beautiful son, Sage. We are still getting along well. I talk to Ashley. Sage [now 19] always sees my daughters, who live in Dallas, and still talks to my son. The relationship is good."

Loaiza broke into the majors in 1995 with Pittsburgh, where he met his first wife, though the marriage ended in divorce after he began seeing Ashley Esposito, the nanny for Ivan Rodriguez's family, following a trade to Texas.
Loaiza broke into the majors in 1995 with Pittsburgh, where he met his first wife, though the marriage ended in divorce after he began seeing Ashley Esposito, the nanny for Ivan Rodriguez's family, following a trade to Texas.Otto Greule Jr/Getty Images

Ashley was the nanny to all three of Rodriguez's daughters—now 27, 24 and 20. Rodriguez says they all live in the Arlington area and continue to keep in close touch. He also says that the relationship between Loaiza and Esposito, who declined comment for this story, didn't cause problems in the clubhouse nor among the Rangers' significant others at the time.

"No, no, no," Rodriguez says. "It was all very nice. I respect their privacy. It was nothing that bothered me. That's life. That's Ashley's life, to be with Loaiza, and by the way, they were a very good couple for a long time. I was very happy, and Loaiza was always very respectful to Ashley as well."

In the divorce, Varrasso said that Loaiza, taking from community funds without her consent, spent, among other things, $64,732.32 on a Lexus for Ashley; made approximate down payments of $30,000 on cars for his sister, mother and brother; and paid $78,436.56 to Ashley's mother, primarily for child care, but also made an additional $6,548.68 in payments to her before the child's birth. There allegedly was another $82,550 in payments made to his mother, $118,745.38 in gifts or loans to other members of his family and approximately $145,000 spent on hotels and airfare for trips Loaiza did not go on, including trips involving Esposito and her family.

Varrasso also claimed Esposito made harassing and threatening phone calls to her throughout 1998, 1999 and 2000 and that in July 2000 Loaiza met Esposito at a resort in Arizona while Varrasso was at a wedding in Mexico, adding that he invited his cousins to the resort and paid for everyone's airfare and hotel.

Referring to herself as a "private person," Varrasso declined comment for this story but in 2013 published a novel, Running for Yellow, a tale of a young lady's self-discovery during a relationship with a professional baseball player who is traded, after which the protagonist receives "a series of harassing phone calls from an anonymous woman claiming to be her husband's lover." She since has remarried and still lives in Pennsylvania.

By 2000, one relationship that had run its course was that of Loaiza and the Rangers. The team was on the verge of slipping into fourth place and was in need of a reboot. Texas had traded impending free agent Juan Gonzalez to Detroit after the 1999 season—but not before an incident that further signaled a deterioration between Loaiza and the club.

During a trip to New York, Gonzalez had purchased a flamboyant, long, leather coat for something like $3,000, according to a source who was with the team at the time, but upon the Rangers' return to Texas, the coat had disappeared. Gonzalez, a character himself who, in 1999, refused to play in the Hall of Fame Game in Cooperstown because his uniform pants were too big, accused Loaiza of stealing it and was going around "threatening to punch his lights out."

At that point, the Rangers decided maybe this guy has some issues.

"I liked Esteban Loaiza. Most people did," the Ranger who requested anonymity says. "The quirkiness he had—when someone said Esteban Loaiza was out washing his car, it was comical. Knowing Esteban, he wasn't doing it to flip people off. It was just him."

But as the Rangers slipped into a descent that led to the free-agent signing of Alex Rodriguez after the 2000 season, late manager Johnny Oates gently approached then-GM Doug Melvin with a message: Look, I know we need pitching, but if you can move him, I'd be OK with it. I'm not going to be critical even if you move him for nothing.

The Rangers made the deal in mid-July 2000, after Loaiza reported late to a game in San Francisco. The next series was in Anaheim, and in the early hours after Texas landed in Southern California from the Bay Area, Melvin finalized a swap to send the right-hander to Toronto for infielder Michael Young and a pitcher named Darwin Cubillan.

In an era before cellphones were ubiquitous, the Rangers couldn't locate Loaiza to inform him of the trade until the next morning.

Before one key start when Loaiza was still in Texas, Eric Nadel, the Rangers' Hall of Fame radio broadcaster, conducted an interview with the pitcher that still makes Nadel chuckle today.

"I said to Esteban, 'This is a very, very important start.' And he said: 'You bet. The whole meat will be on the grill,'" Nadel says.

Though his personal life had become the stuff of gossip, Loaiza's on-field life helped get the Rangers into the playoffs in 1998 and '99.
Though his personal life had become the stuff of gossip, Loaiza's on-field life helped get the Rangers into the playoffs in 1998 and '99.Stephen Dunn/Getty Images

"I asked him, 'What does that mean?' And he said, 'Oh, you know.'"

For Loaiza, there seemed to be more and more on his grill each year.

By the time he was in Toronto, Esposito had been paralyzed because of a benign tumor near her spine that was discovered while she was giving birth to Sage in '01. She spent much of the next year in the hospital and rehabilitation center before she could walk again, leaving her mother and Esteban as Sage's primary caregivers. Between child care duties and the contentious divorce, Loaiza's personal life was a wave of emotions during his two-plus seasons with the Blue Jays. But as a ballplayer, he had a different role to play, that of an inspiring figure to young players, especially those from Mexico.

"He was always the kind of guy who took care of rookies and his countrymen," says Rodrigo Lopez, who pitched in the majors for 11 years and is a Spanish language radio voice of the Arizona Diamondbacks. Like the time Loaiza invited Lopez and his wife to Tijuana for a two-day party celebrating the 50th wedding anniversary of Loaiza's parents, Luis and Maria. Or when he sprung for an expensive steak dinner for the Lopezes when the Blue Jays were in Baltimore during Rodrigo's first season with the Orioles.

"I know creme brulee because of him," Lopez says. "He introduced me to some of life's pleasures."

To this day, Lopez says, he thinks about Loaiza every time he is in Chicago because, among other things, there was a taco joint Loaiza loved.

Loaiza enjoyed the life.

In the offseason, he and Ashley would spend time at their Southlake, Texas, home, hosting neighborhood Christmas and New Year's parties replete with 20-piece mariachi bands in their living room.

When Loaiza would play in Arlington during the season, every now and again there would be parties with music blasting late into the night.

"He was the host with the most," says former Rangers radio broadcaster Josh Lewin, who was Loaiza's neighbor. "Nothing unseemly. It was just a rich neighbor who wants to be a good host."

Loaiza immediately meshed with longtime White Sox pitching coach Don Cooper upon signing with Chicago as a free agent before the '03 season, but on the field, Cooper noticed one giant red flag: In Toronto the year before, Loaiza was more hittable than someone of his talent should have been.

Your stuff is too good to give up this many hits, Cooper told Loaiza. How the hell are you doing it?

"He got snippy with me," says Cooper, who was alarmed by the 11.4 hits per nine innings Loaiza had surrendered with the Blue Jays. "So I said: 'Let's examine it. If you're ahead in the count and giving up that many hits, you're an ass, you're not very intelligent. If it's early in the count, we've got to look at the quality of your early pitches. Are they out when they're supposed to be in? Down when they're supposed to be up?'"

Out of those early conversations came Loaiza's masterpiece: He led the AL with 207 strikeouts that summer and finished second in Cy Young Award balloting to Toronto's Roy Halladay. He threw two shutout innings in the All-Star Game. And the White Sox stayed in the AL Central race all summer before finishing four games out.

Loaiza led the league in strikeouts and finished second in American League Cy Young Award voting in 2003 when he was with the White Sox.
Loaiza led the league in strikeouts and finished second in American League Cy Young Award voting in 2003 when he was with the White Sox.Matthew Stockman/Getty Images

"There were a lot of big sombreros people were wearing during his pregame warm-up every time," Cooper says. "It created a stir. Crowds around the bullpen were noticeable, very noticeable."

On the last day of the season, Sox ace Mark Buehrle volunteered to skip his start to allow Loaiza to go on short rest to give him the opportunity to tie Valenzuela's 21 victories. Loaiza threw 7.1 three-hit innings to beat Kansas City and join the Dodgers legend. Loaiza and the Sox were ecstatic.

But the pitcher's idiosyncratic ways again emerged the following spring when the White Sox were mapping out their rotation. Out of respect for what Loaiza had done in '03, Cooper and new manager Ozzie Guillen asked whether he preferred to start on Opening Day or the home opener eight days later. Loaiza's response: I want both.

Cooper explained that it wouldn't work because the number of days between the road and home openers didn't mesh with the rotation. Loaiza countered by saying he could start on Opening Day, pitch a shorter relief stint a few days later and then come back to start the home opener.

"I wasn't going for that because one, it didn't jibe, and it wasn't the best plan, period," Cooper says. "And two, wait a minute, Buehrle gave up a start for you; he gets one of these."

Though Loaiza was 9-5 with a 4.86 ERA through 21 starts in '04 and made his second All-Star team, the previous season's magic slipped through the cracks. And July 31, less than three weeks after the game, he was reunited with his All-Star manager, Joe Torre. Loaiza was dealt to the Yankees for Jose Contreras and cash, pitched 10 games (six starts) and was the losing pitcher in Game 5 of the epic American League Championship Series in which Boston erased a three-game deficit to stun the Yanks.

Loaiza hit paydirt one more time as a free agent following the 2005 season, signing a three-year deal worth nearly $21.4 million with Oakland.

But while he finished 11-9 with a 4.89 ERA in '06, his life in the fast lane bubbled up into public view for the first time: He was jailed in the wee hours one morning in mid-June, charged with drunken driving and speeding after being caught exceeding 120 mph on an Oakland-area freeway in his Ferrari. Only a day after his release, Loaiza started and earned a win over Seattle. According to court officials familiar with the case, Loaiza was convicted of reckless driving and given a three-year probationary sentence.

"He was just a knucklehead guy with some decent stuff upon occasion," says Oakland radio broadcaster Vince Cotroneo, who was in Texas' booth while Loaiza was there. "He wasn't a bad guy. He was always helpful for what we needed to do. He was a little quirky, but you can say that with a lot of people.

"I went to Oakland and so did he in '06. This was the Lamborghini-driving, Maserati-driving, DUI Loaiza that we got. The paint was starting to dry. You were starting to capture the full portrait of the guy. When he got to Oakland, it got stranger."

Sidelined by neck and knee injuries, Loaiza was waived the following season and scooped up by the Dodgers, only to be released in mid-2008, when a phenom named Clayton Kershaw replaced him in the Los Angeles rotation.

He was just a knucklehead guy with some decent stuff upon occasion.
— Oakland Athletics radio broadcaster Vince Cotroneo

At 36, Loaiza's time in The Show was finished.

"I think when we're young, we all have a tendency to think it's going to last forever," Torre says. "And when you have to move on to something else, I guess you're vulnerable. It's sad."

In so many ways, most of them not known to many around him during this time, Loaiza was extremely vulnerable.

Ovations on the field now silenced, Loaiza, still a hero in Mexico, stepped into another kind of spotlight with a relationship to Mexican American pop star Jenni Rivera.

They met at one of her concerts. She was the top-selling artist in regional Mexican music and referred to by the New York Times and Billboard as one of the biggest stars in the genre. His 126 career victories ranked second in baseball history by a Mexican-born pitcher behind Valenzuela's 173—a mark that stands today.

Together, they were national royalty. They married in 2010, and on July 1, 2011, Loaiza and Rivera were honored with their own stars on the Las Vegas Walk of Stars.

"Well, he pitched, and I caught it," Rivera quipped of how they met, explaining they were fans of each other when their worlds collided.

Loaiza and Jenni Rivera were treated as celebrity royalty in Mexico, and still are honored on Las Vegas' Walk of Stars.
Loaiza and Jenni Rivera were treated as celebrity royalty in Mexico, and still are honored on Las Vegas' Walk of Stars.Julie Jacobson/Associated Press

For Loaiza's baseball friends from Mexico, it was a heady time whenever they'd encounter him, especially if he happened to be with Rivera, who was all over the charts with hit songs such as "De Contrabando" and "Culpable o Inocente." The "Mexican power couple," as they were periodically referred to in the press.

"For us, he was dating the most popular singer at the time," Lopez says. "It was pretty fun. She was very nice."

Lopez scored an invitation to the Loaiza-Rivera wedding, but because it was in September and Lopez was pitching for the Diamondbacks, he had to pass.

What he missed was an unforgettably extravagant Southern California ceremony. Rivera arrived in a horse-drawn carriage, and Loaiza descended by helicopter. Security was tight. Guests' cellphones were confiscated at the door.

Silva, playing professionally in Mexico at the time, says, "Every time we heard from him, it was: 'I'm with Jenni. We're here. We're there. If you guys are in town, come to a show.'"

The marriage widened both Loaiza's world and his popularity in Mexico. The stars awarded him and Rivera in Las Vegas represented only the second time a couple was so honored. The first was Gloria and Emilio Estefan, who shared a star.

"They were basically the J-Lo and A-Rod of Mexico before J-Lo and A-Rod," says John Boggs, Loaiza's longtime agent.

"Together, it was the perfect storm."

Yet while with Rivera, Loaiza was running with some people who made his family uncomfortable, according to several friends and acquaintances. Who knew who was coming and going in her entourage? Certainly, they were different from the baseball crowd.

"I never liked her," one longtime family friend says. "I told him, 'Why marry this woman?'"

But Loaiza was swept away by, as the friend says, "that crowd."

They were basically the J-Lo and A-Rod of Mexico before J-Lo and A-Rod.
— John Boggs, Loaiza's longtime agent, of Loaiza's relationship with Jenni Rivera

Says Janice Deaton, Loaiza's defense attorney: "Everybody's lives just kind of changed after that. That's just not what they were accustomed to."

The marriage, Rivera's third and Loaiza's second, lasted barely two years. By the end of what became a tempestuous relationship, there was speculation that one reason they split was because of rumors Loaiza was embroiled in an affair with the eldest of Rivera's five children, Chiquis, who said it didn't happen. In an interview with the Spanish language news program Primer Impacto, Loaiza said "I've always respected everyone in the household and have no need to get involved with other things and get in trouble because I had my wife and I got married and was in love. I was happy...I married her and had no need to get involved with anybody else."

As the cheers for Loaiza had faded, so, too, had the income that not only afforded him the fast cars and major league lifestyle but also helped support the rest of his family.

Rivera, then 43, filed for divorce Oct. 1, 2012. Ten weeks later, on Dec. 9, she was killed when her plane crashed following a concert in Monterrey, Mexico. Six others, including the two pilots, also died.

Conjecture and conspiracy theories swirled, among them that the crash was tied to a Mexican drug cartel and its kingpin, although a former U.S. Drug Enforcement Administration official told the San Antonio Express-News that he believed the crash was "quite simply an act of God."

At the time of the crash, according to published reports, the Las Vegas-based company that owned the plane was under investigation by the DEA, and the agency had seized two of its planes earlier in the year in Arizona and Texas. The exact cause of the crash has never been determined, and a report by the Mexican Directorate General of Civil Aeronautics found the probable cause to be "loss of control of the aircraft for undetermined causes."

In an audio interview recorded a few months before her death, but not released until December, Rivera revealed that she had received several death threats before the crash.

Had the couple not separated, someone close to Loaiza says, he almost certainly would have been on that plane.

Instead, it wasn't long before he was back in Mexican gossip columns because of another relationship, this one with Cristina Eustace, a singer and television host with whom he had a son, Andreas Esteban Loaiza—and, again, a breakup made very public.

One friend of the Loaizas shakes his head sadly. He's spoken with Esteban's parents since the arrest and says that, initially, they were "devastated."

"His parents didn't believe it," he says. "But they say the way he was making his life lately, anything can happen."

Frozen in time, Loaiza's and Rivera's stars continue to shine brightly on the Las Vegas Strip across from the MGM Grand Hotel and Casino—even given Loaiza's incarceration.

"Once we put a star down, we don't take it out," Pablo Castro Zavala, co-founder of the Walk of Stars, tells B/R. "His is based on sports. We don't deal in private life."

When contacted by B/R for comment on her sister's time with Loaiza, Rosie—Jenni's sister—emailed back: "No thank you. Please don't ask again."

At Loaiza's sentencing March 8, 2019, prosecutors recommended 67 months in custody plus five years of supervised release.

From their perspective, it was a case that warranted more time than the 36 months he received. Not only had Loaiza rented the stash house in his name, but it was also just a block away from an elementary school. He transferred the cocaine from one vehicle to another in the garage of the property. Additionally, through the search warrant that was executed, investigators found bank documents in Loaiza's backpack revealing a number of transfers into accounts in his name along with some withdrawals.

NBC 7 San Diego @nbcsandiego

Watch: Former All-Star pitcher Esteban Loaiza appears in a U.S. court and pleaded not guilty to drug charges involving 44 pounds of suspected cocaine. https://t.co/w6DyTQ8g4D https://t.co/3h5ILay21y

"We believed the quick withdrawals were drug proceeds destined for Mexico," Assistant U.S. Attorney Lawrence Casper, lead prosecutor at the time of the sentencing, tells B/R. "So we argued that this was someone who was involved not in one simple transaction but who had considerable involvement."

In paperwork filed with the court, Loaiza's attorney stated, "Mr. Loaiza made a huge error in judgement [sic] when he agreed to commit this crime" and "Mr. Loaiza pleaded guilty and has waived his appellate rights."

The judge considered a number of mitigating factors, including the fact that Loaiza had virtually no criminal history, just one misdemeanor: the reckless driving charge near Oakland in '06.

"It's tough news for the whole country," says former longtime major leaguer Vinny Castilla, both a countryman and teammate of Loaiza's. "Because he was a celebrity in Mexico."

In baseball, though, where no misstep is overlooked for an opportunity to troll someone, when news of the arrest broke, friends teased Young, who had once been dealt for Loaiza: Hey, you were traded for El Chapo!

During those 13 months between his arrest in February 2018 and Loaiza's sentencing, Loaiza's family and friends rallied around him as best they could. Ashley and Sage traveled back and forth from Texas to San Diego to be present at the court appearances. Boggs, his agent, wrote a note to the judge asking for leniency, explaining that this is a man who, among other things, once donated $50,000 to a San Diego Padres project to build a baseball field for underprivileged children in Tijuana even though he never played for the Padres.

Ashley recruited Ed Cassin, the White Sox's longtime director of team travel, to write a similar letter.

To the judge, he, too, lauded Loaiza's generosity. He wrote of the time the Sox were on the road, brought one of their visiting clubhouse managers and the guy raved to Loaiza about the Tommy Bahama shirt he was wearing.

"After the game, Esty calls him over to his locker and says, 'Take the shirt,'" Cassin recalls in a conversation with B/R.

When the clubbie protested, Loaiza insisted.

"He wouldn't take no for an answer," Cassin says. "He ended up leaving the park that night in a T-shirt. It was just an example I wanted to give to the judge."

Loaiza spent the final days before starting his 36-month sentence preparing breakfast at a San Diego cafe.
Loaiza spent the final days before starting his 36-month sentence preparing breakfast at a San Diego cafe.Scott Miller

Loaiza's last public appearance for the White Sox was at their fan fest in 2018—less than two weeks before his arrest—and, to many there, the retired pitcher, who few knew essentially was now living hand-to-mouth selling his own brand of caps in Mexico, seemed gaunt and tired.

"He didn't have the energy he had," Cassin says.

Others saw signs of decay on social media. Especially alarming to many friends was an Instagram post at the beach revealing a stunning weight loss shortly before he went to prison. Turned out that, aside from everything else, Loaiza had Type 2 diabetes.

Lopez texted after the arrest, but Loaiza failed to reply. Silva visited with his childhood friend and former teammate while Loaiza was out on bail but purposely didn't pry. What Silva figures is that Loaiza got himself in over his head and couldn't escape the deep end.

"That's what I think. You never know what people are into," says Silva, who, while staying in touch, also made sure to keep interactions with Loaiza to a minimum. "You don't know. I would hate to get pulled over with someone who has something on them and now you're in a mess and I lose all my business with my kids.

"What do you say? Everybody he met, always, he tried to help everyone out. Who knows what happened, if he got forced into something. The thing with [Rivera] getting killed, or murdered, in the plane crash, that was all fishy.

"A lot of things are just weird, you know?"

U.S. District Court Judge Janis L. Sammartino, at the sentencing, cited Loaiza's years as a baseball star and delivered a message.

"The story changes," she said to him. "It's not just a success story...But it's still something people can learn from."

Loaiza spent his final days of freedom in a work furlough program at a Corner Bakery chain restaurant at a San Diego mall. He worked predawn hours in the kitchen, making cinnamon roll French toast, All-American scramblers and bacon and cheddar paninis.

A manager, citing corporate policy, says he is prohibited from commenting.

"But he was a really nice guy; everyone here liked him," the manager says. "If you see him, tell him his Corner Bakery family says hi."


Scott Miller covers Major League Baseball as a national columnist for Bleacher Report. Follow Scott on Twitter and talk baseball.


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