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The Problem With Jerry: Buy ... or Sell

Jerry Reinsdorf needs to “pony up” and allocate his resources proactively ... or put the White Sox up for sale

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It’s been a good run.

Well, I suppose that depends on your perspective. But all things considered, since Jerry Reinsdorf purchased majority ownership of the Chicago White Sox for $19 million in 1981, the legacy of the South Side has undeniably improved: Five division titles, an AL pennant, a World Series title after nearly a century-long drought, three MVPs, the recent development of a highly-underrated farm system, an excellent history of community outreach, and a current team valuation of nearly $2 billion.

If Jerry’s tenure ended today, his presence as the owner of the Sox will be remembered as mostly positive. But if he’s not willing to go all-in on the best young team he’s ever built, he needs to sell the team to someone who will.

The fans and the city deserve better. For all of the magical moments and achievements, there is a growing shadow lurking over the team’s reputation. In his 40 years at the helm of the front office, Reinsdorf has paid a proven, top free-agent his true market value exactly three times (Albert Belle, José Abreu, and Yasmani Grandal).

Some defend this as savvy spending, but for all of the relatively successful teams Reinsdorf has built only one claimed a championship, despite playing in a frequently-weak division. This comes in large part from a highly-documented history of passing on marquee free agents. At some point, one needs to ask if more could have been done.

And so, the fans asked. In return, they were promised a new way of doing business.

Rick Hahn, freshly frustrated after losing out on the Bryce Harper and Manny Machado sweepstakes to Philadelphia and San Diego said, “The money will be spent. It might not be spent this offseason, but it will be spent at some point … and it’s money trying to be deployed to put us in the best position to win some championships.”

And you could tell he meant it. But today the window is wide open, and all Sox fans have gotten is a cold draft.

Reinsdorf is clearly gumming up his own works, likely due to his fidelity to the idea that the White Sox are a small-market team. But that feels like a sorry excuse to anyone paying close enough attention. Chicago is the third most-populated city in the country. The fans come in droves when the Sox are winning (and when a global pandemic hasn’t shut the entire world down). It’s clear that the best way to keep the seats filled is to keep the team competitive.

Jerry wants to keep it inexpensive.

Anything You Can Do, I Can Do Cheaper

At present, the Sox have perhaps the best young roster in baseball and only need two or three players to make them a true force for years to come in a competitive, underrated AL Central. But Reinsdorf — who has an estimated personal net worth of $1.5 billion — is gambling on inconsistent projections and crying “poor.” This despite the fact that, at the time of this writing, the current expected White Sox payroll for 2021 is just $128 million.

The Sox payroll in 2011? $127 million.

That was 10 years ago. An entire generation of players has come and gone since. There were at least a dozen free agents of significance available this offseason who would have fit the needs of the Sox perfectly, and every single one of them signed somewhere else. Such negligence is hard to justify, and Hahn isn’t to blame.

Forget inflation: The 2021 White Sox are significantly more talented than a roster where Brent Morel, Gordon Beckham, and Carlos Quentin were starters. Only Mark Buehrle and Paul Konerko turned out to be worth watching, both of whom were closer to retirement than their prime. And yet that roster justified spending as much money as arguably the best young core of talent in organizational history?

The fans deserve better.

Want more perspective? As of this writing, the White Sox are spending less this year than the Giants, Astros, Red Sox, Angels, Nationals, Mets, Phillies, Cardinals, Cubs, and Blue Jays, all teams that are projected to finish the season with a worse record than the Sox.

And perhaps most confounding is that even if the Sox added multiple players to the payroll, they’d be nowhere near the luxury tax threshold. But not doing so drastically decreases their protection against injury, regression, and competitive balance. The Sox don’t have an excuse to neglect to repair their major league roster depth.

Their young core is mostly locked in for years to come. Luis Robert, Eloy Jiménez, Yoán Moncada, Tim Anderson, Abreu, and Grandal have signed long-term deals. Nick Madrigal, Dylan Cease, Michael Kopech, and the promising offensive wunderkind Andrew Vaughn might not all be at the same place in their development, but they are all under team control well into the middle of the 2020s. And it’s widely believed that Lucas Giolito is in line to earn a major extension in the near term (although recent behavior combined with the rapidly rising cost to keep elite pitching talent has Sox fans holding their breath).

But obvious problems remain, and two years have passed since the front office promised this city that verifiably proactive transactions would be made to help the Sox become world champions again. Yet dozens of usable, fitting free agents have now gone by the wayside, often to teams the Sox will have to beat in order to win it all.

It’s clear that the rest of the league remains more steadfast in their efforts to fight for a championship than the Sox, and Jerry should use that as motivation. Instead, he’s gambling with borrowed time.

Even though there are only two or three glaring holes, durability and progression across the board remain a legitimate concern. Are they better than last year? Yes. But are they good enough to win it all? That’s still very much unclear.

A Gambling Problem

A few quality supplemental moves have been made in recent memory, which (combined with Hahn’s now-infamous comments) led the fans to believe more would surely come. Signing Grandal was an excellent decision that has already paid massive dividends. Bringing in Liam Hendriks gives an already-impressive Sox bullpen a clear upgrade over new rival Alex Colomé. New Sox skipper Tony La Russa gives this young team some experienced leadership. And, despite the lack of fanfare, trading Dane Dunning for the wildly-underrated Lance Lynn was a shrewd use of prospect capital to upgrade a weak starting staff.

It’s undeniable the team is technically better now than it was in October.

But how much better? Is this team qualified enough to beat the best teams in seven games? To surpass the Yankees and the Twins? To keep pace with the burgeoning Blue Jays? To hold fast with the remarkable organizational depth of the Rays and the A’s? To beat the Padres, Braves, or Dodgers if the Sox are lucky enough to make it to the World Series?


Grandal, Hendriks, and Lynn are all on the wrong side of 30, as is Dallas Keuchel. La Russa’s hiring drew more scrutiny than praise. And worse, gaping holes at DH, right field, and the starting rotation remain despite the additions made so far. With Dylan Cease struggling to reach his projections and Reynaldo López pitching below replacement level, beyond Lynn, Keuchel, and Giolito the best young Sox team ever assembled is declaring itself World Series favorites while essentially resting its fate on a three-man rotation, seven-man lineup, and hope that their remaining top prospects can evolve into high-end major leaguers by June.

Speaking of Lynn, as Leigh Allan deftly points out in his piece about short-term player rentals, the evidence that he would sign an extension with the Sox is hallucinatory. Not only do these trades have near-zero retention rate for the team acquiring the veteran, Reinsdorf has a well-known history of refusing to pay players in their prime what they’re worth, never mind someone in their mid-30’s who just recently became a perennial Cy Young contender.

The only major signing this offseason (Hendriks) replaced a decent relief pitcher the Sox already had (Colomé); no moves were made to fill a previously-existing gap. For a ball club that has invested in so many veterans on the back end of their career, it should go without saying that this course of action is as disappointing as it is risky.

Losing the Harper and Machado sweepstakes now reads as a prelude to a recurring theme. The potential of acquiring George Springer, Marcell Ozuna, Nelson Cruz, or Michael Brantley devolved into paying an aging Adam Eaton, who is nothing more to this team than a platoon player, $8 million. And with all four of the above accepting deals that were well within the Sox budget, fans are supposed to believe Jerry couldn’t afford them?

Meanwhile, as Vaughn figures to share DH/1B duties with Abreu when he’s ready for the big leagues, the rookie will have no room for error on a team that needs to compete right now. And the alternative, more affordable version of the four big bats listed above, Kyle Schwarber, is no longer available either, as he went to the less-competitive Nationals. It’s truly the Sox loss, as he would have fit their needs perfectly, providing a dominant DH presence in the lineup and a decent outfielder to occasionally spell Jiménez, whose defensive skills are no better than Schwarber’s.

But the likelihood that Jerry would have even considered that route is slim and none.

That’s not the worst of it. In their own division, Minnesota remained persistent in their intention to compete by bringing Cruz back, adding the best lefty on the market (J.A. Happ), the best defensive shortstop in baseball (Andrelton Simmons), and luring Colomé from their division rival to close out games.

Cleveland is also still clearly vying for a division title despite unloading its biggest star; their pitching staff was the best in baseball in 2020 and they still have perennial MVP candidate José Ramírez at the center of a great, young lineup.

And while Detroit and Kansas City will be lucky to win 80 games, both have a propensity towards beating the Sox in games they should lose. But one more quality bat and quality starter would give the South Siders a significant divisional advantage. All this to say, Jerry is not maximizing his opportunity for success.

And he’s certainly not playing the odds.

Rick’s Juice Is Worth The Squeeze

Meanwhile Hahn, who has been unsurprisingly quiet with the press this offseason, seemed despondent when introducing La Russa and didn’t seem excited again until Hendriks was introduced. Rick made it clear that his intentions were to bring in marquee free agents and a manager with recent experience in October. None of that has come to fruition, but that’s not his fault.

The venerable Sox owner, however, who has literally increased the financial value of his team to 100 times what he bought it for, is neglecting to give the best roster in his 40-year tenure as the owner a competitive payroll. And the claim that the pandemic is to blame has been debunked by varying independent economists across the nation. (Never mind that Jerry could literally throw $200 million away and he’d still be a billionaire.)

Naturally, the hypotheticals are intriguing.

In the unlikely event that the Sox had signed Trevor Bauer, Liam Hendriks, and George Springer and left Eaton off the roster, they would still have kept team salary just under the $200 million mark. In time, they surely would risk crossing the luxury tax threshold, but that seems worth the cost and effort if the outcome is a much better shot at multiple championships.

Hahn knows this, Ken Williams knows this, the entire baseball world knows it, and it’s almost certain that Jerry knows it too. But the only thing Jerry is paying for so far are his sins.

Even so, dream scenarios aside, if just one of the four marquee players in this free-agent class was added to what the White Sox have done so far, the team would still likely spend the next five years as king of the American League, or at least as legitimate threats to be. Instead, they have a reasonable chance to be kept out of October baseball — unless everything goes right.

Too bad it almost never does.

The conservative estimates of risk-assessment on regression from Abreu, Keuchel, Lynn, and Grandal might not be offset by the progression of younger players. Injuries are always a problem for every team under normal circumstances, lest we forget that baseball hasn’t had a full, 162-game season in nearly 18 months. And neither the league nor its fans know how the restrictive new Covid-19 regulations will impact play throughout a six-month span.

The forecast for the success of the Sox is astronomical despite an incomplete roster. The pieces put in place are premier talents who figure to evolve into some of the best impact players in baseball. Even so, fans and pundits alike recognize that their roster is not yet complete and a clear lack of financial support seems to be the only factor in keeping things unresolved. Hahn has done everything he possibly can to put the Sox into a position to be consistent winners.

If (or when) his expectations aren’t realized, he will not be to blame.

The Last (Twenty) Five Years

The Sox have spent the last half-decade following the example of the Rays, Cubs, Astros, and Dodgers. But there suddenly seems to be a complete change of direction in how the front office is steering the ship. Harper, Machado, Cole, Wheeler, Springer, Bauer, Ozuna, Cruz ... they all would have been to the Sox what so many other stars were to their respective championship teams. And while only the free agent can ultimately decide where he plays, it’s the owner’s job to make them an offer they can’t refuse.

Imagine if the Dodgers didn’t get Mookie Betts, or the Cubs didn’t get Jon Lester, or if the Astros didn’t bring in Justin Verlander, or if the Red Sox didn’t get Chris Sale, or if the Nationals didn’t get Patrick Corbin, or if the Rays didn’t get Charlie Morton. The Sox needed Grandal to get over the hump, but he’s not the same kind of difference-maker. Adding Lynn and Hendriks might have fit the bill if the team weren’t still short a quality starter and an everyday right fielder.

The Padres, Braves, and Phillies are following the same blueprint, and more confidently so. San Diego brought in the aforementioned Machado (not to mention four ace starters) and Philly snagged superstar Bryce Harper (and added Zack Wheeler for good measure). Atlanta, who brought in Marcell Ozuna as the veteran anchor in the lineup last year, retained his services for the next four seasons with an option for a fifth, and added Charlie Morton to an arsenal of starters who had an excellent 2020 campaign.

As their respective youth develops, all three teams are poised to pounce on their opportunities. Meanwhile in Chicago, Giolito, Moncada, Jiménez, and Robert have the potential to be superstars, but they’re not yet. Grandal will likely boast All-Star caliber numbers this year, but just by way of his age and positional placement, he won’t be a cornerstone franchise player. And it’s unfair to assume Anderson and Abreu can carry that weight alone year after year when the pitching staff puts a minor leaguer on the mound every fifth start.

Springer and Bauer obviously would have solved this issue, but now they’re playing for the competition. Even Ozuna, Corey Kluber, or the ideal Marcus Stroman would have been major difference-makers, but all three are now their rivals. Instead, the Sox are days away from pitchers and catchers reporting with no remarkable additions beyond the bullpen. Grandal, Lynn, and Hendriks do not a superstar make, and the only reason Sox fans have been given for these shortcomings is that they’re a “small-market team.”

Jerry’s reliance on this excuse has exhausted fans for decades. He and Jerry Krause made the same mistake in the ’90s by letting the best basketball team ever built disperse because they feared spending money one year too long. The Bulls went from being the best team in the world to the worst in the league almost overnight. And while Jerry made financial gains as a result, the city of Chicago was left to wonder what might have been if the front office had better supported its players and coaches.

Those trends carried over to baseball, from the player’s strike in the 90’s well into the 21st Century, as the 1994 Sox that were robbed of a chance at a title were forced to disperse and the 2005 Sox team that put on one of the greatest postseason performances in baseball history deteriorated into a top-heavy, unreliable organization. Rather than rewarding the players who made their success possible, Jerry challenged them to find work elsewhere.

Over time, they always called his bluff and the Sox were eliminated from October baseball all but four times over nearly three decades. Yet even after he finally decided to let Hahn spend all this time and effort rebuilding the entire organization with a new vision for the long term, Reinsdorf has now elected to revert to his old ways.

Some things never change.

No More Excuses

It stands to reason that the time has come for the Sox to open up the checkbook. After all, if not now, when? The window of contention has opened ahead of schedule, the rest of the division is relatively evenly matched, the farm system has depth it never before possessed, and the owner is an octogenarian. After years of letting excellent players go elsewhere because he refused to pay elite wages for world-class services rendered, the time has come for Jerry to adequately invest in his own team’s success.

But if he won’t, he needs to sell the team to someone who will. The Sox are now left with no free agency options that will vault them into the same stratosphere as their counterparts, and thus will be forced to trade their hard-earned prospect capital to bring someone else in. If he can’t bring himself to elevate the Sox now, Reinsdorf is sending a clear message that he would rather keep his money and risk watching it all go to waste than invest in dramatically increasing his chances at success.

And at age 84, there’s no reason to believe that will ever change.

Make no mistake, the Sox are still very good. On offense and in the field, they have their infield solidified for the foreseeable future with Moncada, Anderson, Madrigal, and Abreu. They have an elite young outfield duo in Robert and Jiménez with a solid platoon in Eaton and Adam Engel to alternate the corners. And with Danny Medick and a healthy Leury García, the bench figures to be versatile and effective, particularly on defense.

The pitching, for all of the uncertainty surrounding it, could still be effective. Lynn and Keuchel should each provide the rotation with 180+ innings of competitive pitching. Carlos Rodón is as good a bounce-back candidate as anyone, especially for the team that drafted him. And as Cease makes forward progress with newly-minted pitching coach Ethan Katz, Giolito might just be the most underrated frontline starter on any ball club. But even if only three out of the five live up to their expectations, Grandal, arguably the best catcher in the game today, will be their battery mate.

There’s also a very good chance that the other three top Sox prospects will play a sizable role in 2021. Vaughn, Kopech, and the electric Garrett Crochet all have very high floors and look phenomenal in their limited collective professional experience. Plus, if Eaton is the worst player on the team, that’s not a terrible problem to have, even if he is making more than 5% of the entire team’s payroll in 2021.

So although the concern about how the team allocates its resources is thoroughly warranted, Jerry deserves some acknowledgment, too. Not just for what he’s done in recent memory, but for the work he’s done over the years, both on the field and in the peripherals of the organization.

From picking broadcasters to outfitting his stadium, Reinsdorf’s work has been masterful. And his willingness to meet the civil rights movement in 2020 with proactive, actionable change (and support for his players and the city) shines a spotlight on the high caliber human being Jerry is at his core.

Plus, his reputation for being loved by and loyal to his employees precedes him. He’s pleasant in interviews and a genuinely caring and thoughtful philanthropist who loves the city of Chicago and its varied communities. These critiques say nothing of his character or his personality beyond genuine concern for the state of team operations.

Make no mistake: Ultimately, he’s done much more good than harm.

But the time is now. Resting on his laurels will not fill in the gaps and owning a sports franchise includes carrying responsibility when goals are not met. It’s clear Jerry wants to win. That has never been in question. What has fans and the media concerned is his clear desire to avoid spending money to do so. These fears could be assuaged in one fell swoop. There isn’t much left to do; acquiring one or two more top-tier talents would both silence his critics and give his team the best possible chance of success.

Otherwise, what is the point of all this?

Of course, “the devil you know” is something all fans contemplate when there’s ownership change; Hopefully, someone like Tom Ricketts never buys this blue-collar gem on the South Side of Chicago. But if the next maestro puts their money on the field, the focus would be there too.

All this is good reason to keep giving Jerry the benefit of the doubt. But it’s an undeniable fact that he’s had four decades to build sustained success, something that Chicago deserves. And yet, now in his mid-80’s and his opportunity as glaring as it has ever been … he still hasn’t.

The fans and the city have grown tired of relying on unlikely odds, and if Reinsdorf can’t bring himself to deliver the finishing touches on the rebuild now, there’s no reason to believe he ever will. So Jerry either needs to reinvest the fortune he made on the team that gave it to him... or walk away now and let someone else deliver for the city that deserves it. For his sake, he must do one or the other soon.

If he doesn’t, his legacy might not be remembered as he hopes.