2018-2019 Free Agency: A Complete Guide to Machado/Harper for White Sox fans

For context, please consider reading “Is Rick Hahn hinting at a serious pursuit of Manny Machado?” first.

The 2018-2019 free agent class has the potential to deliver a major jolt to the White Sox rebuild. It is uncommon for two young, elite talents to reach free agency in the same year; with an emphasis on “young”, the last such time this happened was when Manny Ramirez and Alex Rodriguez became free agents in the 2000-2001 offseason. Needless to say, they each signed enormous contracts and were bona fide stars for years. This year, 3B/SS Manny Machado and OF Bryce Harper are both free agents, with each player at age 26 on Opening Day 2019. Before I go into what these players might receive on the open market, let’s address some common concerns that Sox fans may have about free agency.

Why would such a talented player like Machado or Harper want to sign with the White Sox?

Money. Spare me the “the Sox are rebuilding and currently not good, so nobody will want to sign here” logic. Free agency is, and always has been, about money. If the White Sox are offering a player the most money, chances are very high that the player will sign with the White Sox. A recent example of a player signing with a bad team for a lot of money is Eric Hosmer, who agreed to a $144 million contract with the rebuilding Padres just last winter. While Hosmer is not nearly as good as Machado or Harper, $144 million is nothing to scoff at. Now, if the White Sox were to offer a player a fairly equal amount of money as teams such as the Yankees, Phillies, or Dodgers, then I believe the player would, in most cases, sign with another team. Therefore, the key here is that the White Sox need to offer the most money, likely with contract opt-outs for the player, to have a good shot. It’s unlikely, but the Sox have the money to actually pull it off.

Why would the White Sox offer so much money to a single player when their biggest signing ever was Abreu’s $68 million deal?

While this is a more valid concern than the previous one, it is still easy to mitigate. For starters, the White Sox have offered players more than $68 million several times. The Sox were one of the highest bidders for the aforementioned Alex Rodriguez in 2000. They were also one of the finalists for Masahiro Tanaka in 2014. Rodriguez ended up signing with the Rangers for $252 million, and Tanaka landed with the Yankees for $155 million. Chances are, if the White Sox offered either of them $68 million or less, they would not even have been reported as a contender.

Secondly, the White Sox have money, and a lot of it. Per Spotrac, the White Sox only have two non-arbitration players under guaranteed contracts for next season- Welington Castillo ($7.25 million) and Tim Anderson ($1.4 million). James Shields‘ contract option will certainly be declined; if he is to return, it will be for much cheaper than the $16 million option he has. Nate Jones has a $4.65 million option, but, per Baseball-Reference, there is a clause in his contract that states that his option will become for the league minimum if he receives elbow surgery prior to the 2019 season. Jones indeed received elbow surgery in 2017, so if the clause is worded properly, his option will only be for about $550,000. After arbitration and pre-arbitration players are factored in, the Sox still figure to have a payroll of no more than $60 million. There is plenty of room in such a payroll for free agent additions.


Do the White Sox want to spend on Machado/Harper, or wait for future free agents such as Arenado and Rendon?

Nobody can really say for sure whether the Sox are enamored with Machado, Harper, or a future free agent. The only evidence of interest is the trade rumors from last December, when the Sox reportedly considered trading for Machado a year early. The risk of waiting for a future free agent is that there is no guarantee that any future free agent actually reaches free agency- this is a risk identified by Rick Hahn himself. What we know now is that Manny Machado and Bryce Harper will hit the open market, so one might guess that the White Sox will at least pursue one of them. Barstool’s WhiteSoxDave asked Rick Hahn directly at a live podcast recording whether the Sox would have the money to compete for Harper and Machado, and while Hahn did not explicitly commit to players by name (because that would be tampering, or dangerously close to it), he did assure the fans that the money will indeed be available for such a player when the time is right.

Why it might happen: Challenging public perception

Much of the White Sox rebuild has included the front office challenging the public perception of the team’s operating procedures. First, the common belief was that the White Sox would never execute a full-scale rebuild. The Sale trade was the start of that myth being put to rest. Then, there were doubts that the White Sox would pay a hefty 100% penalty for signing an amateur free agent, but they did exactly that by signing Luis Robert for a grand total of $52 million, including the penalty. Finally, when Jose Quintana trade rumors were heating up, the Yankees, Pirates, and Braves were considered top suitors with the Cubs being an afterthought, perhaps due to an idea that the teams would never make major trades after the Sammy Sosa trade worked out like it did. Regardless, Quintana was traded to the Cubs out of nowhere. The new doubt out there is that the White Sox will never reel in a big time free agent. While the odds of doing so are obviously not ideal, this myth could be next on the front office’s board.

What might these contracts look like?

Say it’s early-mid December (or even November, if we’re lucky and the market moves very quickly), and Sox fans open Twitter to see it – that one tweet that turns their productivity at work/school down to zero. Whether it’s Ken Rosenthal, Jon Heyman, or even a local reporter, the White Sox are expressing heavy interest in one or both of Machado/Harper. Any team that signs these players has to be careful that a contract does not hamper their long term financial resources, but chances are that both players will command contracts for north of $300 million. There is a small possibility that they do not receive initial offers to their liking, prompting them to sign one year deals for outrageous sums, but assuming teams provide them with substantial offers, each player should sign for deals in the 8-12 year range for $275 million (at the low end) to $350 million, including player opt-outs after the 3rd year or so. A team like the White Sox may benefit from frontloading the contract to maintain spending flexibility down the road, meaning that the player would receive higher sums earlier in the contract and smaller sums as he ages, rather than the same amount of money each year. However, the risk there is that the team frontloads a contract to pay around $40 million per year for the first 3 years, only for the player to exercise his opt-out after the 3rd year, leaving the final deal as 3 years, $120 million, an almost guaranteed overpay regardless of how well the player performs. Despite this risk, I would guess that Machado and Harper each end up signing deals for about 10 years and $325 million with at least one opt-out around the third year.

Time for the hardest part

Whether you’re reading this during the MLB playoffs, the dead period between the end of the playoffs and free agency, or even later, the hardest part for White Sox fans must be waiting for the bidding to begin. Many factors will be in play for the eventual deals that Machado and Harper agree to, but there is not a team in baseball that is better suited financially for long-term spending at the moment than the Chicago White Sox. At the very least, I expect the Sox to be heavily involved in the bidding process. Even if they do not sign one of the two premier talents, I think fans will be pleased with how aggressively the team pursues them, and the contract offer(s) (if leaked by reporters) will be competitive. As I said earlier, if we offer one of the players more money than any other team, chances are very high that the player would sign with us, even if Twitter has you convinced that nobody is ever signing with us. Thus, it’s time to see if Hahn can deliver on what may be a defining winter for the rebuild. The franchise-altering talents are there, the money is there, so if what he has said to fans is true, the time is now.

Featured photo: Bleacher Report
Second photo: Sports Illustrated
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  5. Please. The Sox will play the “we were right there until the end” card. Neither signs with the Sox. But I’m pretty sure there is a .220 hitting DH out there with the first name of Adam the they will be all in on



  6. No Major Market team is better posied to pull this office than the Sox. They could sign both of them to 30m plus and still be in the 130 to 150 million payroll range.

    It’s time to play yo with the big boys.
    The Sox are going to have to end up being close to 200 million.

    The signing of both these guys will send season tickets sales soaring and attendance reaching 3 million.

    There national and international exposure would be through the roof.
    This ownership owes us a compelling product.



  7. Harper will cost the team signing him a draft pick, Machado will not. Machado has also out-WARed Harper over the last 3 seasons. I can see the Sox get into a bidding war over Machado, but they will tread much more lightly with Harper.



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