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Jonathan Singleton

Brewers Reinstate Wade Miley, Jesse Winker From Injured List; Designate Jon Singleton

By Mark Polishuk | June 17, 2023 at 11:46am CDT

The Brewers announced four roster moves, including the activation of both Wade Miley and Jesse Winker from the injured list.  Miley was placed on the 15-day IL due to a lat strain on May 17, while Winker has been on the 10-day IL since May 28 due to a cervical strain.  To create space on the active roster, the Brewers optioned right-hander Tyson Miller to Triple-A and designated first baseman Jon Singleton for assignment.

Miley inked a one-year deal worth $4.5MM in guaranteed money to come to Milwaukee during the offseason, and the veteran southpaw has delivered a 3.67 ERA over 41 2/3 innings.  Miley’s 40.4% grounder rate and 10.3% barrel rate are both significantly worse than in recent seasons, though it’s hard to yet make any big projections given the small sample size of innings.  The lefty has made up for those numbers with a borderline elite 5.3% walk rate, as well as his customary good work at limiting hard contact.

Miley will start today’s game against the Pirates, and his return brings some more relief to a Milwaukee rotation that has been hit hard with injuries.  Brandon Woodruff will still be out until at least the All-Star break and Aaron Ashby will miss all of the 2023 season due to shoulder surgery, but with Miley now back on the mound, the Brew Crew are at least a step closer to their initial first-choice rotation.  Adrian Houser will be shifted to the bullpen, leaving Miley, Corbin Burnes, Freddy Peralta, Colin Rea, and Julio Teheran as Milwaukee’s current rotation.

Winker was another offseason acquisition, picked up from the Mariners along with Abraham Toro in exchange for Kolten Wong.  The trade hasn’t worked out for either team to date, as Wong and Winker have each badly struggled with their new clubs.  Winker has looking to bounce back from a relatively disappointing 2022 campaign in Seattle, yet the 108 wRC+ he posted with the Mariners is far above the 60 wRC+ (off a .204/.315/.231 slash line) that Winker has delivered over his first 127 plate appearances in a Brewers uniform.  There’s still plenty of time for Winker to turn things around, as perhaps the three weeks on the IL both healed his neck problem and might serve as a fresh start to his 2023 season.

The Brewers selected Singleton’s contract from Triple-A earlier this month, and he hit only .103/.188/.138 over 32 PA.  While an underwhelming slash line, just making it back to the big leagues for the first time since 2015 marked a personal victory for Singleton, whose battle with marijuana addiction took him out of baseball entirely for three seasons until he launched a comeback in the Mexican League in 2021.  If Singleton clears DFA waivers and the Brewers outright him to Triple-A, Singleton can choose to become a free agent, since he has been outrighted off a 40-man roster in the past.

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Milwaukee Brewers Transactions Jesse Winker Jonathan Singleton Tyson Miller Wade Miley

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Brewers Place Tyrone Taylor, Darin Ruf On 10-Day Injured List

By Mark Polishuk | June 3, 2023 at 6:43pm CDT

Prior to today’s 10-8 win over the Reds, the Brewers placed outfielders Tyrone Taylor and Darin Ruf on the 10-day injured list.  Taylor (whose placement is retroactive to June 2) is dealing with a right elbow sprain, while Ruf has a laceration on his right knee.  In corresponding moves, Milwaukee called up Blake Perkins from Triple-A, and as reported yesterday, Jon Singleton’s contract was selected from Triple-A.

The new faces delivered today, as Perkins hit a grand slam to help the Brewers score the victory in Cincinnati.  However, losing Taylor and Ruf further thins the Brewers’ depth, as the club now has 14 players (six of them position players) on the injured list.  It isn’t yet known when either player could be back, as Bally Sports’ Sophia Minnaert notes, since Ruf’s laceration is quite severe and Taylor will undergo tests to determine the nature of his elbow problem.

Taylor first sprained his right elbow in late February, which kept him out of action for Spring Training and delayed his 2023 debut until May 2.  Whether due to the lost spring prep time, lingering elbow soreness, or both, Taylor has badly struggled at the plate, hitting only .160/.179/.240 over 78 plate appearances.  It’s a big dropoff for a player who had a solid .241/.303/.453 slash line over 729 PA of part-time duty in 2019-22, and it seemed like Taylor might have been in line for a larger role given the rather unsettled nature of Milwaukee’s outfield.

Ruf just signed the Brew Crew in the middle of May, coming to Milwaukee after he elected free agency rather than accept an outright assignment to the Giants’ Triple-A affiliate.  Stepping into a first base platoon as the right-handed hitting complement to Rowdy Tellez, Ruf also wasn’t hitting much (.531 OPS) over his first 30 PA for Milwaukee before he badly cut his knee during Friday’s game.  Ruf was chasing a foul ball when he collided with the tarp rolled up on the sidelines at the Great American Ballpark.

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Milwaukee Brewers Transactions Blake Perkins Darin Ruf Jonathan Singleton Tyrone Taylor

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Brewers To Select Jon Singleton

By Anthony Franco | June 2, 2023 at 10:35pm CDT

The Brewers are selecting the contract of first baseman Jon Singleton, reports Robert Murray of FanSided (Twitter link). Milwaukee has an opening on the 40-man roster after releasing Luke Voit this week, so they’ll only need to make a corresponding 26-man move.

It sets the stage for Singleton’s first major league action in nearly eight years. A top prospect during his days in the Astros’ farm system a decade ago, he signed a $10MM extension before reaching the majors. Singleton debuted midway through the 2014 campaign but slumped to a .168/.285/.335 line over 362 plate appearances. He’d get into 18 games the following year, with what seemed to be his final MLB appearance coming in October 2015.

After a season and a half in the upper minors, Singleton was hit with a third career suspension for a failed drug of abuse test. The Astros released him and he was out of the sport entirely for a couple seasons. Singleton has since spoken about his struggle with marijuana addiction. After a few years away, he began a comeback in Mexico in 2021. A monster showing there led Milwaukee to add him on a minor league deal for 2022.

Singleton has spent the past season-plus with the Brewers’ top affiliate in Nashville. He hit .219/.374/.439 there last season. The Brewers re-signed him and carried him on the 40-man roster for a spell over the offseason before waiving him on the eve of Spring Training. He returned to the organization on a new minor league deal and is hitting well for the Sounds.

In 48 games, Singleton owns a .259/.387/.489 line. He’s connected on ten home runs, walked at a stellar 17.5% clip and kept his strikeouts to a lower than average 19.3% rate. Singleton showed plenty of patience and power last season as well but he’s putting the ball in play far more consistently this year. He’s sliced his strikeout percentage more than eight points from 27.7% year over year.

As a result, Singleton earns a promotion that marks a huge moment in an incredible comeback effort. He returns to the big leagues a few months shy of his 32nd birthday having overcome the personal hurdles about which he’s been open. Now that he’s back in the majors, he’ll add a left-handed first base/designated hitter option to Craig Counsell’s bench. The Brewers have Rowdy Tellez and Darin Ruf in a first base platoon. The latter suffered a leg laceration in this evening’s game, however, raising the possibility of an injured list stint.

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Milwaukee Brewers Transactions Darin Ruf Jonathan Singleton

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Brewers Re-Sign Jon Singleton To Minor League Deal

By Anthony Franco | February 10, 2023 at 4:35pm CDT

The Brewers have re-signed first baseman Jon Singleton to a minor league contract, the club informed reporters (including Todd Rosiak of the Milwaukee Journal-Sentinel). He’s back with the organization after being released last month and receives a non-roster invitation to Spring Training.

Singleton hasn’t played in the majors since 2015, his second season as a member of the Astros. A one-time top prospect and recipient of a $10MM extension before reaching the majors, Singleton struggled to a .171/.290/.331 line through 114 big league games. He connected on 14 home runs with a massive 14.3% walk percentage but struck out at an untenable 36% clip.

After spending a couple seasons in the minors, Singleton was released by Houston. That came on the heels of a suspension after failing a drug test, with the left-handed hitter later admitting he has battled marijuana addiction. Singleton was out of the sport entirely for a few seasons but embarked on a comeback in Mexico two years ago. A monster 46-game run there earned him a minor league opportunity with Milwaukee heading into 2022.

Singleton spent the year with the Brew Crew’s top affiliate in Nashville. He struck out at a near-28% clip and only hit .219, but he more than compensated with his typical blend of patience and power. Singleton walked at a 20.1% clip to reach base at a strong .375 rate and popped 24 home runs in 581 plate appearances. It didn’t get him a big league call but impressed Milwaukee’s front office enough they re-signed him to a minor league deal at the start of the offseason and quickly added him to the 40-man roster to prevent another team from taking him in the Rule 5 draft.

He didn’t retain that roster spot into the season, as he was designated for assignment once the Brew Crew signed Brian Anderson. After clearing waivers and spending a few weeks on the open market, he circled back to the Milwaukee organization. He’ll have to earn his way back onto the 40-man roster, where he’d hope to join Rowdy Tellez and Jesse Winker as lefty bats in the first base/designated hitter rotation.

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Milwaukee Brewers Transactions Jonathan Singleton

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Brewers Release Jon Singleton

By Anthony Franco | January 26, 2023 at 9:59pm CDT

The Brewers have released first baseman Jon Singleton, according to his transactions log at MLB.com. The move comes a few days after he was designated for assignment once Milwaukee signed Brian Anderson.

Singleton didn’t appear in an MLB game with the Brew Crew during his brief stint on the 40-man roster. He hasn’t played in the majors since 2015, his second season as a member of the Astros. A one-time top prospect and recipient of a $10MM extension before reaching the majors, Singleton struggled to a .171/.290/.331 line through 114 big league games. He connected on 14 home runs with a massive 14.3% walk percentage but struck out at an untenable 36% clip.

After spending a couple seasons in the minors, Singleton was released by Houston. That came on the heels of a suspension after failing a drug test, with the left-handed hitter later admitting he has battled marijuana addiction. Singleton was out of the sport entirely for a few seasons but embarked on a comeback in Mexico two years ago. A monster 46-game run there earned him a minor league opportunity with Milwaukee heading into 2022.

Singleton spent the year with the Brew Crew’s top affiliate in Nashville. He struck out at a near-28% clip and only hit .219, but he more than compensated with his typical blend of patience and power. Singleton walked at a 20.1% clip to reach base at a strong .375 rate and popped 24 home runs in 581 plate appearances. It didn’t get him a big league call but impressed Milwaukee’s front office enough they re-signed him to a minor league deal at the start of the offseason and quickly added him to the 40-man roster to prevent another team from taking him in the Rule 5 draft.

Unfortunately for Singleton, the Brewers’ high rate of turnover this offseason squeezed him out of the picture. Assuming he goes unclaimed on release waivers, he’ll be free to explore other opportunities as a free agent.

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Milwaukee Brewers Transactions Jonathan Singleton

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Brewers Designate Jon Singleton For Assignment

By Darragh McDonald | January 23, 2023 at 1:40pm CDT

The Brewers have officially announced their signing of infielder/outfielder Brian Anderson, making that deal official. In a corresponding move, first baseman Jon Singleton has been designated for assignment, per Curt Hogg of the Milwaukee Journal Sentinel.

Singleton, 31, has had one of the more unique baseball journeys. Drafted by the Phillies in 2009, his strong work in the minors got him onto top prospects lists, jumping onto Baseball America’s top 100 in 2011. At that summer’s deadline, he was one of four players traded to the Astros in the deal that sent Hunter Pence to Philadelphia. Singleton continued to impress after switching teams, launching home runs and walking at very high rates for the next few seasons.

In June of 2014, just as he was to be promoted to the majors, he and the Astros agreed to a five-year, $10MM extension that also came with three club options. The club hoped for Singleton to be a staple of their lineup for years to come and locked him in at an affordable rate before he could increase his earning power. Unfortunately, the plan didn’t come to fruition. Singleton hit just .171/.290/.331 in 2014 and 2015. That led to a wRC+ of 81 indicating he was 19% below league average. He was kept in the minors for the next few seasons and released in May of 2018. At that time, Singleton had just been given his third suspension for a failed test for a drug of abuse. He would later go on to speak publicly with Adam McCalvy of MLB.com about his battle with marijuana addiction.

After getting let go by the Astros, Singleton sat out a few seasons, not playing official baseball anywhere from 2018 to 2020. He joined Diablos Rojos del México of the Mexican League for 2021 and impressed enough to get a minor league deal with the Brewers for 2022. He spent all of last year with the Triple-A Nashville Sounds and produced well overall. He struck out at a 27.7% clip but drew walks at an incredible 20.1% rate and popped 24 home runs. That led to a batting line of .219/.375/.434 and a wRC+ of 118, indicating he was 18% better than league average.

That wasn’t enough for Singleton to get called up during the season, but the Brewers did re-sign him to another minor league deal in October. A few weeks later, they were evidently concerned someone might take him in the Rule 5 draft and added him to the roster prior to the deadline. However, since that time, the club has been quite active despite a lack of splashy free agent signings. In addition to signing Anderson, the Brewers also signed Wade Miley and Blake Perkins and traded for William Contreras, Jesse Winker, Bryse Wilson, Javy Guerra, Payton Henry, Abraham Toro, Owen Miller, Janson Junk, Joel Payamps and Elvis Peguero, in addition to grabbing Gus Varland in the Rule 5 and Tyson Miller off waivers. All of those additions seem to have nudged Singleton out of his roster spot.

The club will now have one week to trade Singleton or pass him through waivers. In the latter scenario, Singleton has a previous career outright and could reject such an assignment in favor of electing free agency. For any club that needs first base help, Singleton could make for an intriguing flier as he’s coming off a strong campaign in the minors and still has less than a year of service time. However, he’s out of options and would need to hang onto a roster spot or else be designated for assignment again.

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Milwaukee Brewers Transactions Jonathan Singleton

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Brewers Select Jon Singleton, Cam Robinson

By Darragh McDonald and Anthony Franco | November 15, 2022 at 5:00pm CDT

The Brewers announced they have selected first baseman Jon Singleton and right-hander Cam Robinson to their roster ahead of tonight’s Rule 5 protection deadline. They also previously announced that infielder Brice Turang and right-hander Abner Uribe have been selected.

Singleton has had a remarkable journey to get back onto a 40-man roster. A member of Baseball America’s Top 100 prospects lists every year between 2011-14, the power-hitting first baseman signed a $10MM extension with the Astros in June 2014. That came in conjunction with his first big league promotion, a precursor to pre-MLB guarantees for players like Scott Kingery, Eloy Jiménez and Luis Robert. Houston’s hope was they’d found a middle-of-the-order presence for years to come, but the left-handed hitter didn’t meet the lofty expectations.

Over the next season and a half, Singleton sputtered to a .171/.290/.331 line in 114 MLB games. After playing the 2016-17 seasons in the high minors, he was released in May 2018. That came on the heels of a third career suspension following a failed test for a drug of abuse. As McCalvy chronicled in greater detail this past spring, Singleton has been open about his battle with marijuana addiction.

Singleton spent a few years out of the game but returned to professional baseball in Mexico last year. He spent the entire 2022 campaign with the Brew Crew’s top affiliate in Nashville, putting together a solid season. Through 581 plate appearances, he hit .219/.375/.434. His batting average isn’t eye-catching, but he connected on 24 home runs and drew walks in an incredible 20.1% of his trips to the dish. Even with an elevated 27.7% strikeout rate, he ranked 15th among 148 International League hitters (minimum 300 plate appearances) in on-base percentage and tied for seventh in long balls.

That wasn’t enough to earn him an MLB roster spot last season, but he re-signed with Milwaukee on a minor league deal last month. He’ll now get back onto the 40-man roster, giving him an inside track at returning to the big leagues for the first time in eight years.

Robinson was a 23rd round pick out of a Florida high school in 2017. The 23-year-old is a pure reliever who’s pitched his way up to Triple-A Nashville. He struggled there but excelled earlier in the year at High-A Wisconsin and Double-A Biloxi. Between the three affiliates, he posted a 2.49 ERA with a 31.6% strikeout percentage over 65 innings.

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Milwaukee Brewers Transactions Cam Robinson Jonathan Singleton

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Brewers To Re-Sign Jon Singleton To Minor League Deal

By Anthony Franco | October 31, 2022 at 11:43am CDT

The Brewers are re-signing first baseman Jon Singleton to a minor league contract, reports Adam McCalvy of MLB.com (Twitter link). The 31-year-old will be in big league Spring Training as a non-roster invitee, McCalvy adds.

It’s a second straight season in the Milwaukee organization for Singleton, who hasn’t appeared in the big leagues since 2015. A member of Baseball America’s Top 100 prospects lists every year between 2011-14, the power-hitting first baseman signed a $10MM extension with the Astros in June 2014. That came in conjunction with his first big league promotion, a precursor to pre-MLB guarantees for players like Scott Kingery, Eloy Jiménez and Luis Robert. Houston’s hope was they’d found a middle-of-the-order presence for years to come, but the left-handed hitter didn’t meet the lofty expectations.

Over the next season and a half, Singleton sputtered to a .171/.290/.331 line in 114 MLB games. After playing the 2016-17 seasons in the high minors, he was released in May 2018. That came on the heels of a third career suspension following a failed test for a drug of abuse. As McCalvy chronicled in greater detail this past spring, Singleton has been open about his battle with marijuana addiction.

Singleton spent a few years out of the game but returned to professional baseball in Mexico last year. He spent the entire 2022 campaign with the Brew Crew’s top affiliate in Nashville, putting together a solid season. Through 581 plate appearances, he hit .219/.375/.434. His batting average isn’t eye-catching, but he connected on 24 home runs and drew walks in an incredible 20.1% of his trips to the dish. Even with an elevated 27.7% strikeout rate, he ranked 15th among 148 International League hitters (minimum 300 plate appearances) in on-base percentage and tied for seventh in long balls.

That wasn’t enough for Singleton to get a big league look, but it was sufficient for the Brewers to bring him back on another minor league deal. He’ll get a chance to compete for an MLB job next spring. Milwaukee can retain both of their 2022 first basemen, Rowdy Tellez and Keston Hiura. Like Singleton, Tellez is a left-handed hitter whose profile is carried by his power and plate discipline. He’s clearly above Singleton on the depth chart, although he’s projected by MLBTR contributor Matt Swartz for a $5.3MM salary in his second year of arbitration eligibility. That’s not an insignificant sum for a Brewers team with a huge arbitration class, and as MLBTR’s Maury Ahram explored earlier this month, it wouldn’t be a surprise if Milwaukee fields trade offers on Tellez this offseason.

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Milwaukee Brewers Transactions Jonathan Singleton

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Brewers Sign Tyler White, Jon Singleton To Minors Deals

By Anthony Franco | December 9, 2021 at 6:05pm CDT

The Brewers announced this morning that they’ve signed first baseman Jon Singleton to a minor league contract. Robert Murray of FanSided, meanwhile, reported (on Twitter) that Milwaukee is also in agreement with first baseman Tyler White. Minor league contracts for players not a 40-man roster at the end of last season are still permissible during the lockout.

White and Singleton are both best-known for their time with the Astros. The former debuted in the majors in 2016, serving as a part-time righty bat to work into the first base/designated hitter mix. After a very strong .276/.354/.533 showing across 237 plate appearances in 2018, White looked on his way to cementing himself as a long-term fixture on the roster. The former 33rd-round pick struggled to a .208/.308/.304 mark in 279 trips to the dish between Houston and the Dodgers the following season, though, and he hasn’t made it back to the big leagues since.

In 2020, White signed on with the SK Wyverns of the Korea Baseball Organization. He only made nine appearances in South Korea, and he returned to the U.S. this past season. White signed a minor league deal with the Blue Jays last winter. Despite a .292/.424/.476 showing with the Jays’ top affiliate in Buffalo, he didn’t get a big league shot with Toronto. White, owner of an impressive .306/.406/.523 line across five seasons at Triple-A, will try to play his way back into the big leagues with the Brew Crew.

Singleton has only appeared in two major league seasons, but he may be the more well-known of the Brewers’ two new first basemen. The left-handed hitter appeared among Baseball America’s top 100 overall prospects every season from 2011-14. In June 2014, Houston signed Singleton to a $10MM contract extension before he made his major league debut, a precursor to similar pacts for players like Scott Kingery, Evan White, Eloy Jiménez and Luis Robert.

The Singleton deal didn’t pan out as the Astros had hoped, as he hit just .171/.290/.331 across 420 MLB plate appearances from 2014-15. He spent the next two seasons in the high minors, and Houston released Singleton in May 2018, not long after he was suspended for the third time in his career after testing positive for a drug of abuse. (Singleton had been open in the past about his struggle with marijuana addiction).

Singleton hasn’t played in affiliated ball since his release from the Astros, but he did return to professional baseball this year. Now 30 years old, he suited up with the Diablos Rojos del México, mashing at a .321/.503/.693 clip over 189 plate appearances. That’s a small sample in an incredibly hitter-friendly environment, but it was eye-opening enough to earn him another chance in the affiliated ranks.

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Milwaukee Brewers Transactions Jonathan Singleton Tyler White

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The Astros Made A Precedent-Setting $10MM Investment…That Didn’t Pay Off

By Mark Polishuk | May 16, 2020 at 8:05pm CDT

It isn’t any secret young and controllable star talent is just about the most valued commodity in baseball, and over the last three offseasons, we’ve seen four instances of clubs looking to gain even more potential control (and score a future payroll bargain in the process) by extending players before they have made their Major League debuts.

Scott Kingery inked a six-year, $24MM deal with the Phillies in March 2018 that also contains three club option years, meaning that Kingery’s contact could ultimately become a nine-year, $65MM pact.  The White Sox inked both Eloy Jimenez and Luis Robert to six-year deals (with two club option years) over the last two offseasons, with Jimenez signing receiving $43MM and Robert $50MM in guaranteed money.  The Mariners also got in on the action with first base prospect Evan White last November, signing White to a six-year deal worth $24MM in guaranteed money and up to $31.5MM more over three seasons’ worth of club options.

The logic for the teams is simple.  An early-career extension eliminates any of the service-time manipulation we so often see with top prospects, and thus the Phillies, White Sox, and Mariners were or will be able to get the players into their lineups as soon as possible.  The clubs were willing to bet that their youngsters would provide immediate dividends at the MLB level, and thus would become more expensive as they entered their arbitration years, so these extensions lock in cost certainty over those arb years and also give the teams control over 2-3 free agent seasons.  Those free agent years could become extraordinarily valuable if, as hoped, these players develop into star big leaguers — we’ve already seen quality production from Jimenez and Kingery in 2019.

From the perspective of the four players, there is also sound reasoning in signing these extensions so early in their professional careers.  The quartet has guaranteed financial security for themselves and their families before even seeing so much as a big league pitch…or, in White’s case, even a Triple-A pitch.  (In Robert’s case, this is actually his second big payday, as Chicago gave him a $26MM bonus as an international amateur in 2017.)  No matter how confident a prospect may be in their ability, the transition to the majors is always something of an unknown.  There’s always the risk of a fluke injury scuttling a promising career, or perhaps a player — like so many star minor leaguers in the past — simply doesn’t produce against MLB competition.

It’s also fair to assume that, before putting pen to paper on their extensions, Kingery, Jimenez, White, and Robert all considered the case of Jon Singleton.  The former Astros first baseman was the first non-international player to sign an extension before the start of his Major League career, agreeing to a five-year, $10MM deal with Houston back in June 2014.  Singleton’s deal contained three club option years that added up to $20MM if were all exercised, plus another $5MM more in potential bonuses.

All in all, it could have been a $35.5MM contract over eight seasons had Singleton lived up to his potential.  Unfortunately for both Singleton and the Astros, that promise didn’t develop into a reality.  After hitting .171/.290/.331 over 420 plate appearances in 2014-15, Singleton never played in the big leagues again, and didn’t play any affiliated ball in 2018-19 before signing with a Mexican League team this past April.

Singleton was an eighth-round pick for the Phillies in the 2009 draft, and he came to Houston as part of the trade package in the deal that sent Hunter Pence to Philadelphia at the 2011 trade deadline.  As one of the early building blocks of the Astros’ total rebuild process, Singleton picked up where he left off in the Phils’ farm system, beating up on minor league pitching and quickly becoming a staple of top-100 prospect lists.  His stock was never higher than during the lead-up to the 2013 season, as Baseball Prospectus ranked Singleton as the 25th-best prospect in the sport, and MLB.com and Baseball America weren’t far behind in slotting Singleton 27th.

In both 2012 and 2013, however, Singleton tested positive for marijuana, and he served a 50-game suspension during the 2013 season.  Marijuana addiction was an ongoing problem for Singleton, as he spoke openly in 2014 about his efforts to break his addiction, including a month-long stay in a rehab facility in 2013.  As it happened, Singleton’s issues continued to plague his career, leading to a 100-game suspension prior to the 2018 season after the first baseman failed a test for a drug of abuse for the third time in his pro career.  Houston released Singleton in May 2018.

Needless to say, these off-the-field problems provide an important detail in looking back at Singleton’s decision to accept the Astros’ offer.  Signing the first “pre-career” extension made Singleton a notable figure in baseball transaction history, and it also opened him up to some rare public criticism from his peers.  Such veterans as Mark Mulder and Bud Norris were open in their displeasure with Singleton’s deal (and, more specifically, the advice given to Singleton by agent Matt Sosnick), arguing that the Houston prospect had shortchanged his future earning potential.  As Mulder put it in a tweet, he questioned if Singleton “doesn’t believe in himself to be great.”

Almost six years after the fact, of course, Singleton made the right choice.  Shortly after his extension was announced, MLBTR’s Jeff Todd wrote a detailed piece about the wisdom of Singleton’s decision in the context of several other top first base prospects and comparable players, noting how relatively few of those players ended up topping Singleton’s $10MM guarantee, and many of those who did top the $10MM figure had the benefit of some actual Major League success.  Plus, there was also the additional element of Singleton’s drug issues — coming off two suspensions and a lackluster 2013 season in the minors, one can certainly understand why Singleton was attracted by the security of an eight-figure contract.

Looking at the extension from the Astros’ end, the Singleton extension can be chalked up as a definite miss.  Calling it a true “mistake,” however, is a stretch.  Considering the money Singleton surrendered due to his 2018 suspension, the Astros’ overall investment in the first baseman ended up being less than $9MM, which was a more than reasonable bet to make considering Singleton’s high prospect ceiling at the time.

The early-career extension was a key tactic of then-general manager Jeff Luhnow, as he navigated through all of the young players amassed in trades and draft picks during the Astros’ lean rebuilding years.  George Springer also received an extension offer before his MLB career even began, as Houston reportedly tabled a seven-year, $23MM deal in September 2013.  Matt Dominguez and Robbie Grossman also received extension offers either before or just after their big league careers got underway.

These other examples illustrate the pros and cons any young player must face in deciding on an extension.  In Springer’s case, he made the right call in turning down that extension, as he has already made more than $28MM in his career and had agreed to a $21MM salary for 2020 (though that number will now be reduced by an as-yet-determined amount due to the shortened 2020 season).  On the flip side, Dominguez and Grossman probably both would have been happy to have Singleton’s $10MM deal in hindsight — Dominguez hasn’t played in the majors since 2016, and Grossman has yet to hit the $10MM mark in career earnings despite racking up 675 appearances with the Astros, Twins, and A’s over the last seven seasons.

It could be telling that there was almost a four-year gap between Singleton’s contract and the next pre-career extension in Kingery, as teams may have been wary of making such a commitment given how Singleton underachieved.  Baseball’s transactions marketplace also underwent some significant changes between 2014 and 2018, with the stagnant free agent winters of 2017-18 and 2018-19 perhaps underscoring how free agency was no longer a guaranteed pot of gold at the end of the service time window for many players.

With four pre-career deals in three years, it stands to reason that we will see more of these contracts in the future — especially perhaps in the wake of the coronavirus pandemic, as financial security could become even more of a priority for players.  Much will depend on how Kingery, Jimenez, Robert, and White live up their deals, and whether or not Singleton will continue to be the lone cautionary tale for teams trying to score themselves a bargain on the extension front.

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Houston Astros MLBTR Originals Jonathan Singleton

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