From the All-Star Game to prison with Esteban Loaiza, MLB ace turned drug lord

A hearty crowd of 47,609 crammed US Cellular Field in Chicago, Illinois, for the 2003 Major League Baseball All-Star Game. A further 13.8 million watched on television across America, one of 200 countries that beamed the Midsummer Classic to enrapt audiences. Shortly after 7:40pm CT, Esteban Loaiza, ace of the hometown White Sox and starter for the American League, strode to the mound amid raucous cheers. This was everything the 31-year-old Mexican had ever wanted, his moment on the biggest stage after an arduous journey through baseball’s backwaters. This was the culmination of immense hard work and unwavering faith through years of dedication. This was the zenith of a wild career that soon went down in flames.

Working briskly, the lean Loaiza induced a ground ball from Édgar Rentería to lead off, shortstop Alex Rodriguez scooping and flipping gracefully to Carlos Delgado at first base. Jim Edmonds followed with a dunked single to right, but Loaiza gritted his teeth and retired two all-time greats – Albert Pujols and Barry Bonds – on lazy fly balls to end the inning. The lanky right-hander pitched a scoreless second, as well, getting Gary Sheffield and Scott Rolen to pop out either side of a swinging strikeout by Todd Helton. Seven up, six down, zero runs allowed.

The septet Loaiza faced combined for 3,192 home runs, seven World Series titles and 10 MVP awards in 133 big league seasons. He dealt with them all nonchalantly, though, entirely unperturbed, as if born for such high-stakes drama. Mission accomplished, Loaiza ambled toward the dugout – a shower of appreciation flooding his path, a world of promise at his feet. Nobody knew it yet, but he would never have a better day. There would be many darker days, in fact, the likes of which rarely befall such distinguished professional athletes.

* * *

Esteban Antonio Loaiza Veyna was born in Tijuana, Mexico, in 1971 and hopscotched between there and San Diego until late adolescence. Baseball offered escapism from the bleak and barren terrain, but Loaiza was not especially gifted athletically. The Pittsburgh Pirates signed him as an undrafted free agent pitcher in 1991, but little was expected of young Esteban, who figured to max out as a minor league fill-in. To that end, the Pirates ferried Loaiza through their farm system – from Augusta to Salem to Carolina – until he earned an unexpected call to the big leagues in 1995.

A rubber-armed swingman, the workmanlike righty earned a 4.88 ERA with Pittsburgh, Texas and Toronto over the next eight years. As detailed in an excellent Bleacher Report portrait by Scott Miller, through 2002, Loaiza’s most notable contribution to baseball lore was a tabloid-esque affair with Ashley Esposito, the 19-year-old nanny of legendary Rangers teammate Ivan ‘Pudge’ Rodriguez. Loaiza was married to his first wife, Christina Teadora Varrasso, at the time, and the affair eventually led to their divorce.

On the field, Loaiza signed a cheap minor league deal with the White Sox in 2003, and the discovery of a wicked cut fastball saved his career from mundane obsolescence. Esteban was an aberration in Chicago, a 2.21 ERA in the season’s first half landing him the unexpected All-Star Game start on home turf. Loaiza was perhaps the best pitcher on earth for a transient spell, and even the mighty New York Yankees coveted his services in trade talks. Starting the Midsummer Classic affirmed his growing reputation, and a dazzling performance stoked the hype.

Loaiza finished the 2003 campaign with 21 wins, tied with Fernando Valenzuela for the most by a Mexican-born pitcher in a single MLB season. A 2.90 ERA and 207 strikeouts in 226.1 innings yielded Cy Young Award consideration, and Loaiza finished second to Roy Halladay in the voting, securing a place among the elite echelon of modern pitchers.

Loaiza also made a decent start to the 2004 season and returned to the All-Star Game, held at Minute Maid Park in Houston. Loaiza again faced Rentería, Pujols, Bonds and Rolen, plus the formidable Sammy Sosa, en route to another scoreless inning. Less than three weeks later, he was finally dealt to the Yankees – for José Contreras, another enigmatic pitcher – just one minute before the 4pm ET, July 31 trade deadline.

Loaiza did not adjust well to the bright lights of New York, however, an ugly 8.50 ERA in pinstripes illustrating his struggles. Loaiza was so bad down the stretch in 2004 that he lost his place in the Yankees’ starting rotation. Come October, Loaiza was relegated to bullpen mop-up duty as the Bronx Bombers collapsed infamously against the rival Boston Red Sox. Ignominy beckoned for the once-prized pitcher, whose stock continued to plummet.

In fairness, Loaiza rebuilt his reputation with the Washington Nationals in 2005, parlaying a reduced 3.77 ERA into a three-year, $21.4 million free agent contract with Oakland. Loaiza showed glimpses of brilliance with the Athletics, but injuries derailed the downward slope of his supernova career. A brief stint with the Dodgers merged into a final flurry with the White Sox before Loaiza retired in 2008, having made more than $43 million in 14 big league seasons. Not bad for an unheralded junkballer, but that handsome fortune was squandered in double-quick time.

* * *

Industry whispers long portrayed Loaiza as a liberal spender who chased the high life. He smoked lavish cigars in the Oakland clubhouse and posed for pictures in the process. He bought fancy clothes from high-end designers. He drove Lamborghini and Maserati cars in rotation. “Oh, how he loved his cars – sports cars, fast cars, sleek cars,” wrote Miller for Bleacher Report. “Luxury watches and clothes, too. He enjoyed every bit of The Show, and the perks that came with the paychecks.”

An air of supposed invincibility engulfed Loaiza. During the 2006 season, he failed a sobriety test while driving a Ferrari at 120mph on the 580 Freeway in Oakland. Athletics general manager Billy Beane banned alcohol in the team’s clubhouse while Loaiza spent a night in jail. At court, Loaiza was convicted of reckless driving and handed a three-year probationary sentence – a harbinger of upheaval to come.

Seemingly unbothered, Loaiza continued to push the boundaries of big league exuberance. According to Miller, Loaiza bought homes for his parents, brother, sister and cousin, in addition to gifting them cars and other luxury items. Those around Loaiza relied on him for sustenance, creating a toxic culture of co-dependency that mangled the athlete’s generosity. Indeed, reports suggested Loaiza had lost most of his career earnings by 2010. The former All-Star lived a hand-to-mouth existence just two years after retiring – a shocking fall from grace that only got worse.

Around that time, in 2010, Loaiza married famed Mexican-American singer Jenni Rivera and frequently appeared on a reality television show – I Love Jenni – that chronicled the exploits of her family. Alas, divorce papers were served in October 2012, only for Rivera to die tragically in a private plane crash two months later.

Loaiza filed a lawsuit against the plane owners – Starwood Management LLC and Rodatz Financial Group – alleging wrongful death. In the complaint, Loaiza argued that the 78-year-old pilot and co-pilot were not licensed to carry paying passengers. Loaiza also claimed a Starwood executive had previously been imprisoned for faking aviation safety records, but the case was dismissed by the Los Angeles County Superior Court.

Interestingly, papers filed during the wrongful death lawsuit explained how Loaiza ‘received and was continuing to receive material support and other valuable financial benefits from Jenni Rivera.’ Indeed, members of the Rivera family accused Loaiza of attempting to profit from Jenni’s death – a sad bookend to a once-illustrious career.

The tone was seemingly set, and Loaiza became fodder for Mexican gossip columns post-retirement. Rumours surfaced of an affair between Loaiza and Jenni’s daughter, Janney Chiquis Marin, with some reports saying it prompted their eventual divorce. Marin denied those rumours, which have never been proven, but the stench of taboo followed Loaiza wherever he went.

In 2013, for instance, Loaiza entered another tempestuous relationship – this one with Cristina Eustace, a singer and television host. The couple even had a son together before another messy public breakup in early 2016. Loaiza saw his love life splashed across the tabloids, though he eventually settled into a lengthy relationship with Mexican businesswoman Ross Labra. Chaos reigned behind the scenes, and an emphatic coup de grâce bubbled to fruition.

* * *

Seemingly broke, Loaiza gradually became embroiled in the seedy underworld of California crime. An ongoing drugs probe by San Diego Police and the Organized Crime Drug Enforcement Task Force (OCDETF) led to surveillance of Loaiza, who was eventually pulled over by officers – driving a Mercedes Benz SUV – on 9 February 2018. Though sniffer dogs did not find drugs in the car, the vehicle was laden with cocaine when Loaiza took possession of it. The former pitcher drove to a townhouse he rented in Imperial Beach and hid the drugs before being stopped by police, who found the illicit address on a handwritten note while searching the SUV.

Searched under warrant, more than 20 kilograms of cocaine – street value: $500,000, according to the San Diego county sheriff’s department – were found at the townhouse, stored beneath baseball equipment bags and in a parked Nissan minivan. Loaiza was charged with felony counts of possession or purchase of narcotics and transportation or sale of narcotics. He duly swapped Yankee pinstripes for a khaki jail jumpsuit – disgrace a constant companion.

Per court documents, bail was initially set at $200,000, and Loaiza’s counsel approached three separate bondsmen in San Diego, seeking support. One of those firms, Acme, agreed to guarantee a bail bond with a 12% deposit. However, Loaiza was unable to pay the $24,000 fee, and subsequently appeared at San Diego County Superior Court in Chula Vista, California, on 14 February 2018. There, Loaiza entered a not-guilty plea, but deemed a potential flight risk, saw his bail bond rise to $250,000. Defence attorney Janice Deaton proposed a bond reduction, saying Loaiza was ‘broke or close to it.’ A series of hearings gradually reduced the bond, and Esposito – the aforementioned nanny of Pudge Rodriguez who lived with Loaiza for eight years and co-parented their son – used her Texas home (valued at $166,000) as collateral to guarantee the bail funds. Loaiza was then released on house arrest on 11 May 2018.

Three months later, in August 2018, Loaiza agreed a plea deal, admitting charges of intention to supply cocaine in return for a reduced prison sentence. Amended bail conditions allowed Loaiza to work via furlough while awaiting sentencing, and in October 2018, the former All-Star took a job working the sunrise shift at Corner Bakery Café in Fashion Valley, San Diego. “He worked predawn hours in the kitchen,” reported Miller, “making cinnamon roll French toast, All-American scramblers and bacon and cheddar paninis.”

In a sentencing memorandum, while seeking a more lenient penalty, Deaton highlighted the charity work undertaken by Loaiza, who built baseball fields in underprivileged areas of Mexico during his career and donated equipment to poor kids. Nevertheless, on 8 March 2019, the former All-Star ace was sentenced to three years in prison for knowingly and intentionally possessing 20 kilograms of cocaine with intent to distribute.

“As a professional athlete, Esteban Loaiza earned tens of millions of dollars and the admiration of baseball fans across the U.S. and Mexico,” said Robert Brewer, prosecuting attorney, while summing up the case. “And yet he sacrificed his reputation – and now his freedom - to become a cocaine trafficker. No one is above the law, and that includes Major League pitchers.”

Karen Flowers, a special agent with the Drug Enforcement Agency, offered a similarly succinct conclusion: “Mr. Loaiza lived every young boy's dream as an All-Star baseball player. And yet, he chose to be a drug dealer. He chose to break the law for profit. He chose to make a buck off someone's addiction. Today, society chose to hold him accountable and took away his freedom.”

Prisoner number 68072-298, Loaiza served his sentence at Federal Detention Centre, SeaTac, in Seattle, Washington. In an ironic yet unintentional nod to baseball’s regular season, Loaiza earned 162 days off for good behaviour, according to the Daily Mail, and was released on 6 August 2021. Deportation to Mexico followed soon thereafter, his rapid demise complete.

* * *

Back in Tijuana, Loaiza feared for his life, according to reports. Mexican media outlets carried news of death threats and questionable acquaintances. It became difficult to discern fact from fiction in the murky post-retirement morass of Esteban Loaiza, and presumptive conjecture often replaced substantiated fact in discussions of a fallen giant.

However, just as it did decades earlier, baseball offered an escape, a passport to a better life. Loaiza returned to the game in April 2023, joining El Águila de Veracruz of the Mexican League as pitching coach. “It is a pleasure to be on the playing fields, and I feel especially honoured to wear the Águila uniform after so many years of not being active in baseball,” Loaiza told the Excelsior newspaper. “I seek to contribute my knowledge to assemble a good team for this season.”

A quandary arose early in the campaign, though, when Veracruz travelled to Laredo, Texas, for a three-game series against the Tecolotes de los Dos Laredos, who split time between Mexico and the US. As a deported felon, Loaiza was not allowed to cross the border, per the Los Angeles Times. The consequences of his misjudgement echoed for years, a legacy resistant to repair.

* * *

There is an unmistakeable Breaking Bad vibe to this entire story, which seems destined for the pathos-drenched, sepia-toned hyperbole of Netflix – all ominous desert vistas, cars abandoned at roadside and the background hum of canned ballpark crowd noise. Though it may seem morose, the whole story fascinates me, not least because I watched Esteban Loaiza during his prime, and his unforeseen demise is a reminder of human fallibility.

Elite professional sports can often seem abstract to gawping fans – a soap opera devoid of feeling. But this is real life, with real consequences – both for Loaiza and for others, including those who may have succumbed to the drugs he tried to push. Still, for all his troubles, there is part of me that wishes the guy well. I hope he lives more peacefully these days, with the fresh perspective that comes from being humbled.

Loaiza is now 52, and though terms of his deportation were never disclosed, I hope he can return to the US one day – if desired. More pertinently, I hope he can be welcomed back into the baseball fraternity, thawed as a stigmatised pariah. After all, this game should not turn its back on former players – especially in their hours of gravest need. With the right safeguards in place, and with rehabilitation following retribution, it would be good to see Esteban Loaiza at the ballpark again – to forgive, if not to forget, and to give a cavalier character a more dignified conclusion.


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