50 Million reasons to trade andrew painter

Numbed by a sport awash in data, whose stadium scoreboards instantly display metrics for thousands of ordinary at-bats and tens of thousands uneventful pitches, whose 30 teams are now steered in part by research directors and quantitative analysts, it is understandable that the average Philadelphia Phillies fan takes little note of a set of numbers that has taken the team four years to compile: $2.9M, $6.9M, $14.3M, and $50.1M.

Those rapidly escalating dollar amounts are what the Phillies will have paid from 2022 through 2025 in Competitive Balance Taxes – the penalty that MLB assesses annually to teams that surpass the salary threshold established for each season by the Collective Bargaining Agreement.

This season’s eye-popping $50-million CBT penalty has two drivers.

One is the Phillies Projected 40-Man Competitive Balance Payroll. At $309M, it races past this season’s $241M threshold by a whopping $68M, registering as the third highest CB Payroll in the National League. It is a remarkable fact of baseball economics that the Phillies 2025 salary is more than the combined team salaries of the Saint Louis Cardinals and the Milwaukee Brewers.

The other driver is the progressive tax rate tied to recidivism. Because this is the fourth consecutive season in which the Phillies will surpass the CBT threshold, and because they are surpassing multiple CBT spending tiers this season, they will be smacked with an effective 80% tax rate on their collective overages. Welcome to the adult table.

This breakneck spending spree is a notable reversal of form for an organization that had never surpassed the CBT before 2022, a parsimonious streak dating back 25 years.

Team owner John Middleton’s laudable largesse has not yet produced a parade, but in a seminal season that finds his team with a mere half-game divisional lead at the All Star break, it does produce questions about the sustainability of the Phillies payroll approach and the direction team executives will pursue at the trade deadline.

Gary Sheffield. Miguel Cabrera. Chris Sale. Hall of Fame caliber talent acquired by GM Dave Dombrowski in three different decades, to bolster World Series runs by the Marlins, Tigers, and Red Sox.

Randy Johnson. Trevor Hoffmann. Elite Hall of Fame talent, traded away by GM Dave Dombrowski when both were raw, unpolished players.

That version of Dave Dombrowski, gunslinger and gambler, who can easily be imagined applauding Jordan Belfort’s excesses and grinning during The Deer Hunter Russian Roulette scenes, has not surfaced here.

Instead, since being named President of Operations in December 2020, Dombrowski’s trades have been safe and uninspired; his role in roster shaping has yielded average returns, especially given the organization’s loose purse strings.

For context, consider that all of the following foundational blocks were assembled on the watch of the oft-maligned Andy McPhail-Matt Klentak regime: the Bryce Harper signing, the initial Zack Wheeler signing, the trades for J.T. Realmuto and Cristopher Sanchez, the amateur selections and signings of Aaron Nola, Alec Bohm, Bryson Stott, and Ranger Suarez. A talented core for Dombrowski to inherit and guide across the finish line.

NO STAIRS WAY TO HEAVEN

In the spring of 2022, following the Phillies 10th straight year of missing the playoffs, Dombrowski got to work, sort of, plugging holes through aggressive spending.

Kyle Schwarber and Nick Castellanos were signed to long-term contracts that added $40M annually to payroll. Both were key contributors in the World Series and 2023 playoff runs. Schwarber has remained a slugging force, a 2025 All-Star now in his walk year.

After the euphoric World Series run, the Phillies extended Dombrowski’s contract for 5 years. He inked Trea Turner to a massive 11-year, $300M deal that winter. Taijuan Walker was signed to an inexplicable 4-year deal for $72M. The tandem added another $45M to annual payroll.

Last off-season, after the NLDS flop against the Mets, Dombrowski traded for starting pitcher Jesus Luzardo at reasonable prospect cost; the move fortified a team strength.

But when it has mattered most the last four years, with an organizational mandate to lay claim to the Commissioner’s Trophy, Dombrowski’s in-season trades and strategic off-season adds have netted Kyle Gibson, Ian Kennedy, Noah Syndergaard, Brandon Marsh (for Logan O’Hoppe), David Robertson, Craig Kimbrel, Michael Lorenzen, Austin Hays, Carlos Estevez, Rodolfo Casto, Jordan Romano, and Max Kepler.

It was retread Syndergaard on the hill for Game 5 of the World Series, opposing Justin Verlander, the AL’s Cy Young Award winner that year. It was 35-year-old Kimbrel (released by LA the previous season) imploding against the Diamondbacks, collecting crucial losses. It was playoff virgin Estevez serving up Franciso Lindor’s backbreaking slam.

Not a Matt Stairs or Joe Blanton in the pedestrian bunch.

WHAT ARE OUR PROSPECTS

The general expectation across baseball, and a source of endless fodder for Philly sports talk radio, is that the Phillies will be aggressive deal makers this trading season. Why have a $309M payroll, and more pointedly, why incur $50M in luxury tax penalties, if not to push more chips to the middle of the table? Why not give this veteran core, motivated by last season’s quick playoff ouster, their final shot at redemption? Prospects be dammed, right?

Well, maybe.

The answers to three questions should guide how the organization plays its hand.

Question One: Is it possible to address the team’s deficiencies and still not improve the team’s chances of winning the World Series?

This requires come-to-Jesus soul searching.

At the All Star break, FanGraphs calculated the Phillies to have a 9.7% chance of winning the World Series – the third best odds in MLB and a nod to the team’s SP talent and playoff experience. The unquestionable favorite is the LA Dodgers at 21.2%.

The road to an NL pennant – let alone a world championship – goes through a team with an enviable roster of star talent (active and injured) hungry for a repeat. It is backed by ownership with an appetite and track record for spending that dwarfs the Phillies: in 2025, the Dodgers are projected to have a Competitive Balance Payroll of $403M and a CBT Penalty payment of $154M.

By the time the playoffs begin, the front of the LA rotation is likely to include ace Yoshinobu Yamamoto, ace Shohei Ohtani, and 2-time Cy Young Award Winner Blake Snell. Expect the Dodgers to use their enviable farm system and surplus of MLB-ready talents like Dalton Rushing, Emmett Sheehan, and Alex Freeland  to bolster their pen and upgrade an OF slot. It should surprise no one were LA to add another accomplished SP at the deadline, too.

If the Phillies do not win the NL East and earn a round-one bye by compiling the second-best record in the National League, they could square off against LA as soon as the NLDS.

Question Two: What is the team’s identity?

After the dick-swinging contest with LA has been completed, an existential question – chewed on by Jean Valjean and countless amnesiacs – awaits owner John Middleton: Who Am I?

Are the Philadelphia Phillies limitless spenders now? Does it give Middleton any pause to know that the team’s current modus operandi has the Phils on track to outspend the Brewers by $170M and yet have one fewer win at the break?

Does paying $50M in luxury taxes come with lost opportunities – dollars that could have yielded improvements if spent elsewhere – or is it just chump-change ante, the cost of a Quixotic quest?

If Middleton truly does not mind paying exorbitant luxury taxes, he is going to love 2026: the team has already committed $163M for only seven players.

And were the Phils to reach agreement with free agent Kyle Schwarber on a deal averaging $30M annually, sign JT Realmuto for $10M as a stop-gap, and pony-up modest service-time bumps to Alec Bohm and Bryson Stott, the springtime 2026 Competitive Balance Payroll would sit at $215M and account for less than half of the opening day roster!

Question Three: How will the voices in the Phillies war room be weighted?

In early July, Baseball America updated its Top 100 Prospects List; it included six Phillies, with familiar names like Andrew Painter and Aiden Miller and a breakout player, infielder Aroon Escobar. This type of representation, a mix of domestic and international players scouted, signed, and developed by Brian Barber and Preston Mattingly the last five seasons, is encouraging.

Both executives are young and talented; Mattingly has risen to a role of Assistant President and General Manager. Barber has risen to Assistant General Manager, with a focus on amateur scouting. Sam Fuld is currently earning an MBA in preparation for a 2026 role as President of Business Operations.

Have the wunderkind executives earned the right to be heard, really heard, on how aggressive the team should be at this year’s trade deadline, a team they will inherit and oversee shortly? Do they favor holding onto as much of this talented crop of kids as possible?

Does Middleton still have full faith and trust in Dombrowski to do Dombrowski things, things that brought titles to two other franchises? Does it matter at all that Dombrowski will be stepping down in two years?

PREDICTION: ALL IN

The Goliathan that is the Los Angeles Dodgers is ignored. Middleton soldiers on with spending and expresses a willingness to take on more contract dollars through trade; there really is no turning back once $50M in luxury taxes is on the ledger.

With full-throated endorsement from ownership, Dombrowski dials a recent ex, the Boston Red Sox. They hook up on an 8-player blockbuster: Alex Bregman, Jarren Duran, and Aroldis Chapman for Alec Bohm, Andrew Painter, Orion Kerkering, Mick Abel, and Justin Crawford .

Bregman adds slugging to this year’s team and can be extended through the 26-27 seasons, providing cover against the loss of Schwarber. Duran is an athletic OF under club control — a blend of pop and speed with the ability to play left and center. Chapman is a rental with deep playoff experience; at age 37, he has posted a 40% K rate this season and still averages 99 mph on his sinker.

The Sox get Philadelphia’s 1st, 4th, and 6th ranked prospects, along with Bohm — who has one year of club control remaining — and an intriguing 8th-inning arm in Kerkering. The Painter and Abel acquisitions address one of the few areas of need for Boston’s stellar farm system.

The all-in approach satisfies the Phillies fanbase. The team does not win it all. Middleton, who once turned smoke into $2.9B, is left to ponder the irony of watching $50M go up in smoke.

Twenty Five Years of Phrustration:

The Phillies, Outfielders, and the Amateur Draft

Are you good at guessing hardcore Phillies trivia? What do Kyrell Hudson, Cord Sandberg, and Cole Stobbe have in common?

All were third-round selections by the Phils in the MLB Amateur Draft. All were outfielders — taken in 2009, 2013, and 2016. All never made it above the AA level.

I know this minutiae because I recently took a deep dive into the Phillies amateur draft history on www.thebaseballcube.com, an archival treasure trove.

I was interested in finding out the last time the Phillies drafted an impact outfielder, using this filter: a major league regular who earned full-time at-bats (500+) for more than 2 consecutive seasons.

The results of the search startle and disappoint in equal measure, revealing only one such player: Pat The Bat Burrell in 1998.

That’s 25 years of drafting ignominy.

Twenty five years of Greg Golson, Dylan Cousins, Kelly Dugan, and Roman Quinn.

Twenty five years of Mike Costanzo, Zach Collier, Larry Greene, and Cornelius Randolph.

Twenty five years of Mickey Moniak, Adam Haseley, Luke Williams, and Scott Kingery.

To be clear, the players listed above are not late-round dart throws. They were all selected in the first 3 rounds of drafting, signifying that in the estimation of the Phillies thinktank they were among the Top 90-100 baseball talents available from the domestic collegiate and high school ranks.

In three amateur drafts since 1998, the Phils did not select any outfielder in the first 10 rounds.

Brown, Byrd, and Bourn

While identifying only Burrell as an impact outfielder, my search did turn up a few near misses. Dom Brown, a 20th rounder in 2006 (you probably forgot he was picked that late) played two full-time seasons in 2013 and 2014 and made an All-Star team; the rest of his resume produces agita.

Marlon Byrd was a 10th rounder in 1999 who compiled 25.8 WAR over a decent (late-blooming) career. But Byrd only had 1,000 career at bats for the Phils, and just one season with over 500. He was traded to Washington for the immortal Endy Chavez in 2005.

If there’s a pony in the pile, it’s Michael Bourn, a second rounder in 2003. Mind you, Bourn only had 144 plate appearances as a Phillie but he was intriguing enough to be traded to Houston in 2007 for a package that returned Brad Lidge. Bourn compiled 22.8 WAR in his career and twice had 60+ SB in a season, both for the Astros.

I point out the WAR totals of Byrd and Bourn because they both ended up amassing higher career WAR than Burrell, who labored a bit defensively while playing nine seasons for the Phillies and 12 seasons overall.

PHlailing In International Waters, too

The Phillies have also failed to mine outfielders from burgeoning international markets. They unearth shortstops and pitchers and the occasional catcher, just not anything resembling productive outfielders.

This drought is happening against the backdrop of savvier organizations regularly plucking and grooming MLB caliber outfielders, including transformative talents like Ronald Acuna, Juan Soto, Julio Rodriguez, and soon, Jackson Churio.

The failure on the international front is not from lack of aggression. In 2015, the Phils lavished Jhailyn Ortiz with a $4M signing bonus, but that grand gesture fizzled and now stings; Ortiz was designated for assignment last week.

When they do sign athletic, toolsy outfielders, like current hopefuls Johan Rojas and Yhoswar Garcia, their hit tools invariably seem to plateau and their prospect status downgrades from promising to platoon-type player. Fingers crossed on Rojas.

It is important to remember that MLB dictates the size of the annual spending budget available to teams for international signings, leveling the playing field for smaller markets like Pittsburg and Kansas City. So it is not a matter of the Phillies getting consistently outspent by the Yankees or Padres or Dodgers or Mets on the international stage; they simply have a systemic inability to identify and develop outfield talent – on a college campus or on a backfield in the Dominican Republic.

You Get 20 Million, And You Get 20 MillioN…

The long-standing failure of the Phillies to draft and develop outfielders is more than a curiosity; it is a flaw that forces the organization to mimic the largess of Oprah Winfrey in order to sway and pay free agents they desperately need to compete in a tough division.

Trace the trail of tears that began in 2013 — Randolph, Kingery, Williams, Moniak, and Haseley — and it leads directly to the big-ticket, long-term contracts proffered to Schwarber and Castellanos — $20M per year each for one-dimensional sluggers better suited for DH and roles on the dirt, but who have found themselves manning corner OF spots since their arrivals.

So here we are at the start of the 2023 season, and the Phillies are strapped to a 40-man Competitive Balance Tax total of $255 million – the fourth highest in baseball and $22M over the threshold.

It is their second consecutive overage, subject to 30% penalty. On this year’s Opening Day payroll of $243M, nearly 30% of it was allocated for the salaries of three free-agent outfielders.

It feels like this is an organization at a bit of a crossroad — with all chips pushed to center table, desperate for an encore — but already taking in water from injuries that cannot be plugged deftly because of the limits of roster construction and shallow minor league depth. Will they continue adding to the bloated payroll? Do they grasp at the brass ring once more while Aaron Nola is still in pinstripes?

While I appreciate John Middleton’s generosity and public optimism, the approach does not seem sustainable or realistic.

The naked truth is that the Phils only have two low-cost, controllable assets – Alec Bohm and Bryson Stott — to ameliorate the breakneck spending. Brandon Marsh may develop into a reliable player; he also may be fronting an Allman Brothers tribute band within five years. Ranger Suarez could be a bargain for the next few years, but the health of his left arm became a most unwelcome question mark this spring.

Critically important to the overall outlook, the Phillies will soon learn whether crown jewel Andrew Painter will pitch again this year, possibly contributing to the team in the second half, or require elbow surgery that stalls his full-time arrival in South Philly for a year, maybe more.

Where Have You Gone, Johnni Turbo?

Speaking of the naked truth, to satisfy your morbid curiosity, I created a table that lists all of the outfielders taken by the Phillies in the Amateur Draft since 1998. Enjoy the trip down misery lane. For the record, Johnni Turbo (2006) and Gauntlett Eldermire (2010) are real names.

And be sure to stew on this nugget: from 2004 through 2017, the Phils selected an OFer in the first round six times. These six first rounders combined to collect only 421 mostly-empty ABs with the big club, a return worse than banks provide on savings accounts.

I am a Phillies fan, so it is my sincerest hope that the outfielder taken in the first round in 2022, Justin Crawford, is at least half the player his father was and that the young man delivers ten years of productive outfield play for the Phillies.

The last time that happened, Ed Rendell was mayor and Blockbuster was still operating 6,500 stores.

OUTFIELDERYEARDRAFT ROUND
PAT BURRELL19981
ERIC VALENT19982
JORGE PADILLA19983
JASON MICHAELS19984
JASON COOPER19992
MARLON BYRD199910
2000NO OF PICK FIRST 10 ROUNDS
CHRIS ROBERSON200019
JAKE BLALOCK20025
MICHAEL BOURN20032
JAVON MORAN20035
JORDAN PARRAZ20036
GREG GOLSON20041
SEAN GAMBLE20046
MIKE COSTANZO20052
JERMAIN WILLIAMS20057
JEREMY SLADEN 20058
JOHHNI TURBO20064
QUINTON BERRY20065
MICHAEL TAYLOR20075
ZACH COLLIER20081
ANTHONY GOSE20082
KELLY DUGAN20092
KYRELL HUDSON20093
AARON ALTHERR20099
GAUNTLETT ELDERMIRE20106
LARRY GREENE20111
ROMAN QUINN20112
DYLAN COUSINS20123
CAMERON PERKINS20126
CORD SANDBERG20133
2014NO OF PICK FIRST 10 ROUNDS
CORNELIUS RANDOLPH20151
SCOTT KINGERY20152
LUKE WILLIAMS20153
MICKEY MONIAK20161
COLE STOBBE20163
ADAM HASELEY20171
DAULTON GUTHRIE20176
MATT VIERLING 20185
2019NO OF PICK FIRST 10 ROUNDS
BARON RADCLIFF2020*5
ETHAN WILSON 20212
JORDAN VIARS20213
JUSTIN CRAWFORD20221
GABRIEL RINCONES20223