Will Reinsdorf finally put his money where his mouth is?

Jerry Reinsdorf will have some difficult financial decisions to make soon as owner of the Chicago White Sox.
Jerry Reinsdorf will have some difficult financial decisions to make soon as owner of the Chicago White Sox. / Nuccio DiNuzzo/GettyImages

The Chicago White Sox's problems on the field this season could pale in comparison to those coming soon off the field.

The White Sox and owner Jerry Reinsdorf will have numerous important and pivotal payroll decisions to make starting after this season.

Pitchers Lucas Giolito, Kenyan Middleton, Reynaldo Lopez, catcher Yasmani Grandal and infielders Elvis Andrus and Hanser Alberto will be unrestricted free agents at the end of this season.

But that's just the start of the White Sox pending free agent parade.

The contracts of shortstop Tim Anderson and pitchers Liam Hendriks, Mike Clevinger, Lance Lynn, Kendall Graveman, and Joe Kelly will expire after 2025.

Pitchers Dylan Cease and Michael Kopech and third baseman Yoan Moncada could jump into the free-agent waters after 2026.

The Chicago White Sox are a team that needs help going forward.

The White Sox's lack of impactful roster moves in recent years is about to come to an end.

That's the good news, given the team's disappointing performance on the field the last two seasons. The bad news, as the old saying goes, is that he who pays the piper calls the tune.

Will Reinsdorf, the one who has to pay the piper for the White Sox's now frustrating rebuild, pick all of the right tunes?

Will he even pay the piper?

Don't forget that the White Sox refused to pay first baseman Jose Abreu after the 2022 season, even though the Houston Astros got him for just $58.5 million for three years.

Also don't forget that the White Sox are one of just three current teams (along with the small-market Oakland Athletics and Kansas City Royals) to never give out a contract of at least $100 million.

The largest contract in White Sox history is the $75 million given to Andrew Benintendi this past offseason for five years through the 2027 season. Grandal got $73 million for four years through the end of this season.

The Chicago Cubs gave one player (Dansby Swanson at $177 million) this past offseason more than the Sox gave Benintendi and Grandal combined. That's how two teams in the same city supplement a rebuild.

The Sox try to cut corners financially. The Cubs throw their wallets around.

So, yes, don't expect the White Sox to jump with both feet into the Shohei Ohtani sweepstakes after the season. Joc Pederson and Jorge Soler, who will also become free agents this offseason, are more the White Sox speed.

Nobody is saying Reinsdorf is cheap or doesn't spend money. He's paid failed general manager Rick Hahn for a decade after all. The White Sox also have the 11th-highest payroll in baseball this season at roughly $184 million.

Shouldn't $184 million buy you a team better than 23-35 two months into the season.

Reinsdorf actually should be commended for being close to the top third in all of baseball in payroll. The Sox, after all, is 23rd this year in home attendance and 29th in road attendance, reinforcing the fact that the franchise is a small market team trapped in a big market.

The White Sox live in a big market but they are simply paying rent. The Chicago Cubs own the market, averaging 32,000-plus fans a game. That's why they can afford a $177 million shortstop.

Will the Sox give Anderson $177 million this offseason or next? That seems like a stretch for a team averaging 18,000 fans a game.

But don't blame Reinsdorf for being a little hesitant to open up his wallet. He's been burned repeatedly through the years.

Does anybody think Benintendi is worth $75 million? What about the $73 million Grandal got starting in 2020? Those are the most lucrative contracts the White Sox have ever paid out and they have gotten about a 50-cent return on their investment for every dollar.

Remember the $55.5 million the Sox gave Dallas Kuechel for three years starting in 2020? You can bet Reinsdorf remembers.

Reinsdorf, given the White Sox's failures in free agency, simply won't throw his money at problems. If he did he would have gone out and bought a real manager this offseason (see Bruce Bochy in Texas) to correct a problem (Tony La Russa) he created himself.

It's difficult as a Sox fan to trust Reinsdorf.

This is a guy who, after all, said when he bought the team in 1981 that he sees his job as a public trust.

A decade later Reinsdorf was seriously threatening to move the White Sox to Florida.

Reinsdorf, through Hahn and Kenny Williams, asked White Sox fans to be patient through the rebuild because championships were coming. So they then go out and supplement the rebuild with Kuechel, Grandal, and Benintendi and are now a dozen games under .500.

Is another full-scale rebuild coming?

Reinsdorf is now 87 years old and might not cherish the thought of another long, painful rebuild. But never forget that his only loyalty over the past four-plus decades with the White Sox and the Chicago Bulls is to his faithful employees, investors, and, of course, bottom line.

Notice we didn't mention fans or the standings.

He's not going to change, not at 87 years old. But if he doesn't change, the Sox will let a ton of talent walk out the door one by one over the next three or four years.

It's doubtful Anderson and Giolito, after all, will preserve the White Sox's tradition of never handing out a contract of at least $100 million.

Giolito, who will turn 29 in July, will likely seek something along the lines of four or five years for well over $100 million.

Giolito is certainly not Gerrit Cole, who signed a $324 million deal with the New York Yankees in 2020. But two guys who can never stay healthy got $162 million (Carlos Rodon) and $185 million (Jacob DeGrom) this offseason.

Anderson, despite his slump this year, likely won't sign anywhere for under $150 million when he becomes a free agent after next season. He will turn 30 later this month and this will be his first and likely last chance at a huge deal.

Four shortstops signed the past off-season, ranging from Dansby Swanson ($177 million) to Trea Turner ($300 million). Carlos Correa got $200 million despite teams worried about his long-term health.

Wander Franco got $182 million after his 2021 rookie season from the cash-poor Tampa Bay Rays.

Moncada, Kopech, and Cease might also shatter the White Sox's $100 million glass ceiling in a few years. Luis Robert, a free agent after 2028, and Eloy Jimenez (after 2027) will more than likely get north of $200 million.

Reinsdorf is heading into a new, expensive baseball world he simply might not be able to handle. That very same reason, after all, was why he was able to buy the White Sox in the first place in 1981 from Bill Veeck.

Veeck, who couldn't afford to even paint old Comiskey Park, was devoured by free agency in the late 1970s. Why do you think one of the first things Reinsdorf did as Sox owner was to sign Carton Fisk?

He wanted to show he was a more capable owner than Veeck, who really wanted to sell the team to Eddie DeBartolo Sr.

Veeck, though, had an excuse for his struggle as an owner. He bought the team after the 1975 season before anyone really knew what free agency was going to do to the sport.

Reinsdorf has no excuse.

He bought the team with Eddie Einhorn and roughly three dozen investors for just $20 million. The White Sox are now worth just under $2 billion. The Bulls, which he bought for about $9 million in 1985, are now worth around $4 billion.

The Sox, we remind you, fixed their second base problem this offseason by signing an aging Elvis Andrus for $3 million for one year and replacing La Russa with Grifol, a former Kansas City Royals bench coach.

Is Anderson or Giolito worth a $150 million investment? Certainly not right now. What bout Cease and Kopech in a few years? Robert, Moncada, and Jimenez aren't going to sign anything under nine figures.

It really doesn't matter whether or not the players deserve the money. The market, not Reinsdorf's stinginess, will determine all of that.

You either pay up or start over.

History tells us the Sox will simply start over. Again.

Next. The 15 worst contracts in Chicago White Sox history. dark