Editorials White Sox

Sailboats, Submarines, and Subterfuge: The Race For MLB’s Two Mammoth Free Agents

Many Major League Baseball teams have been looking forward to the free agency period following the 2018 season with a particular sense of purpose for many years. The reason for such an emphasis on the period following the ’18 season is not because of any structural or rule changes to how free agency would be implemented, but rather, because of the players reaching free agency during this period. While the ’18 free agency class is certainly deep (although perhaps not as deep as one might have expected, due to some players not reaching the market, as well as the falloff in performance by others), make no mistake about it – the ’18 free agency class is primarily about two megastars – Bryce Harper and Manny Machado.

The Moment

For years, Major League front offices have been mapping out their payrolls seasons in advance, trading away players or refusing to sign others making significant salaries, all in an effort to position their respective teams to make a run at one of the most elusive commodities in the game: the superstar player entering the absolute prime of his career.

To be clear, it’s not entirely uncommon for superstar players to reach free agency, however, it is extremely uncommon for players of such awe-inspiring talents to reach free agency at the pinnacle of their powers. This is because Major League Baseball entitles clubs that draft players in the Rule-4 First-Year Player Draft to several years of “service time,” or in other words, to control the rights to a player for essentially six or seven seasons once a player ascends to the Major Leagues. The practical result of this practice is, putting aside questions of equity and fairness, is that even the best players typically do not reach free agency until they are 29 or 30 years of age.

Without digging into too much data, it is generally presumed that the prime years of a ballplayer’s career occur between the ages of 26 and 32. Thus, by the time many players reach free agency, particularly in a market that has almost fully transitioned to a cold reliance on advanced analytics, they already have several of their best seasons behind them.

The Targets

Harper and Machado, as in many other respects, are different in this regard. Both players are reaching free agency at the age of 26. This is because both Harper and Machado reached the Major Leagues in their age 19 seasons. Therefore, it is widely believed that the teams ultimately signing the players will be receiving production from the prime of their careers. And for that, teams will pay handsomely – so handsomely in fact – that it is expected the respective contracts Harper and Machado will each sign will eclipse the total value of the largest contract signed in Major League Baseball history, that of Giancarlo Stanton with the Miami Marlins for $325 million.

Sailboats and Submarines

As one might expect, the early pursuit of Harper and Machado, or at least the reporting by the media of that pursuit, has been dizzying. While certain teams, such as the White Sox and Phillies are obvious fits for one or both Harper and Machado due to their significant payroll capacity below the luxury tax threshold, other teams, such as the Dodgers, Yankees and Cubs, are undoubtedly lurking. As uber-agent Scott Boras commented at the GM Meetings in Carlsbad, CA back in November:

“Look, this is a submarine race, not a regatta. You do not want other teams knowing that you’re interested in a generational player.”

While this is undoubtedly true to some degree, just how many submarines are hunting Harper and Machado beneath the surface is probably a lesser number than Boras and Dan Lozano, Manny Machado’s agent, might have clubs believe. Meanwhile, the White Sox and Phillies have little choice but to attempt to track down Harper and Machado in plain sight, brightly colored sails and all.

Despite all their subterfuge, it is widely believed that without making significant alterations to their rosters, namely moving veteran players with significant salary attached, the Dodgers and Cubs are simply unlikely to make the type of offer necessary to land players of Harper or Machado’s caliber.

While there is no hard salary cap in baseball to technically prohibit any club’s payroll obligations from reaching a certain threshold in any given year, a Competitive Balance Tax (more commonly referred to as the “luxury tax”) is in place which discourages teams from exceeding thresholds, as they trigger significant financial penalties, and in particularly egregious cases of excessive spending, even result in a team’s first selection in the Rule-4 First-Year Player draft being moved back ten spots.

Additionally, both the Dodgers and Cubs have existing rosters among the most talented in baseball. While each would undoubtedly jump at the chance to add a player like Harper or Machado, the addition of one of these players would likely be viewed more as a luxury than as the cornerstone the Phillies and White Sox are willing to pay for. As such, it is unlikely that significant shuffling of existing rosters in both LA and Chicago – already rich with talent – will be viewed as a prudent maneuver due to the risk of fixing something that isn’t broken.

The Yankees, however, are a more curious case. Not only are they Major League Baseball’s premier franchise, they happen to find themselves in a position that is unlike any other in baseball: significant payroll capacity below the luxury tax and a talented roster which has reached the postseason each of the last two seasons.

Despite this confluence of desirable attributes, something the Yankees don’t necessarily have is a drastic need for either Harper or Machado. An outfield depth chart featuring Giancarlo Stanton, Aaron Judge, Aaron Hicks, Brett Gardner and Jacoby Ellsbury seems to allow little room for an addition of Bryce Harper.

Machado, on the other hand, is believed to be viewed by most teams as a better defender at third base than his natural shortstop position he played prior to moving to accommodate Baltimore shortstop J.J. Hardy. The emergence of Miguel Andujar, despite his defensive shortcomings, would put the Yankees in a somewhat awkward position of considering a trade of a young potential all-star should they wish to add Machado at his most effective defensive position on the diamond.

While Machado could certainly begin the season at shortstop for the Yankees, as Didi Gregorious is expected to miss a significant portion of the ’19 season recovering Tommy John surgery, the question of who will play where when Gregorious returns would likely be a problem Brian Cashman is open to solving. And yet, Cashman is holding his cards close to his chest when it comes to a potential Machado fit somewhere on the left side of the Yankees infield, and owner Hal Steinbrenner has made it clear he did not enjoy Machado’s “Johnny Hustle” comments in the midst of the Dodgers postseason run. Confusing, you say? That’s likely just the effect Cashman desires in his team’s potential pursuit of Manny Machado.

The Phillies and White Sox, to work off of Scott Boras’ marine metaphor, never had much of a chance to submerge their desire to land one or both of Harper and Machado. Whether it be due to very public and obvious payroll data showing significantly light financial commitments on the horizon, or a need to placate proud fanbases desperate to emerge from the depressing doldrums of extensive rebuilding efforts, the Phillies’ and White Sox’s intentions have been suspected by even the most novel seaside observers for months, if not years. The outlook on the chances of each, however, could not be more different upon first glance. Phillies owner John Middleton brazenly and famously commented (and almost certainly by now wishes he hadn’t) “[w]e’re going into this expecting to spend money, and maybe even be a little stupid about it.”

Meanwhile, White Sox owner Jerry Reinsdorf, who despite paying Michael Jordan more than $30 million in consecutive seasons more than twenty years ago, is seen as extremely conservative when it comes to putting so many eggs in one basket. To date, Reinsdorf has never signed a contract for a White Sox player with a total value of more than $68 million.

Despite the perhaps extreme juxtaposition of their views on finances, the organizations Middleton and Reinsdorf control share more commonalities than differences. While the Phillies’ rebuild is likely one year ahead of the timeline of that of the White Sox, both organizations are well-positioned to succeed in the near future. Each organization is in various stages of building a young, affordable, and most importantly, talented roster. Each organization, as a result of the above, has significant capacity to add payroll below the luxury tax.

And perhaps most importantly, each organization is either currently (the Phillies are set to enter the fourth year of a 25-year, $5 billion deal), or in the coming seasons (as in the case of the White Sox) primed to experience an increase in revenues related to a lucrative television contract. While big dollar television contracts in major markets are becoming more commonplace among Major League Baseball teams, they have the inevitable result of counteracting the League’s efforts at leveling the playing field, whether through caps on international spending, the First-Year Player Draft, the luxury tax and revenue sharing.

Television money – particularly an infusion of nine-figures annually – allows clubs in major markets an advantage middle and small market teams may stave off for some time, but likely cannot overcome over the long haul.

The Negotiations

At Major League Baseball’s annual offseason spectacle, the Winter Meetings, and perhaps in the weeks leading up to it, Bryce Harper and his agent Scott Boras met with potential suitors and exchanged information on a number of topics, including current rosters, farm systems, potential off the field marketing opportunities, etc.

Manny Machado, along with his agent Dan Lozano, are expected to visit somewhere between three and six organizations beginning the week of December 17th. The known destinations on the Manny Machado tour are the White Sox, Phillies and Yankees, and each will likely pitch the twenty-six year old star on a long-term marriage likely to result in sustained postseason success.

Make no mistake about it, however, this game of high-stakes poker is just beginning. Once the presentations have been given, and the various organizational luminaries have been presented, Scott Boras and Dan Lozano will begin soliciting the organizations for their initial offers. It’s unknown exactly how many of the particulars will be included in these initial offers, but it’s expected that the teams will each leverage their own unique situations to attract the player.

For example, the White Sox and Phillies might offer contracts that are frontloaded – where the player receives a disproportionate percentage of the contract in the initial years of the contract – thus providing greater present day worth versus a contract where more of the money comes in later years or is even deferred beyond the term of the contract.

The contracts that Bryce Harper and Manny Machado ultimately sign will undoubtedly be complicated and innovative in nature. They will guarantee more than three-hundred million dollars, will span 10 years or more in duration, and they will contain provisions for the player to opt out after a designated number of years. The following is a discussion of what the structure of these contracts might look like.

The Money 

Giancarlo Stanton signed a 13 year, $325 million dollar contract with the Miami Marlins in late 2014. It eclipsed the total value of Miguel Cabrera’s 10 year, $292 million contract with the Detroit Tigers signed earlier that year, as well as Alex Rodriguez’s 10 year, $275 million pact with the Yankees in 2008. In late 2015, Zack Greinke signed a 6 year, $206.5 million deal with the Arizona Diamondbacks, and established a new record for average annual value, at $34.42 million per year.

Scott Boras and Dan Lozano will both be looking to better both the total value, as well as the average annual value of the Stanton and Greinke contracts, respectively. While it is unknown just how long a duration Harper or Machado are open to, if we assume each player requires at least a 10 year contract, that would establish a floor of approximately 10 years, $345 million for each player. Does a market exist for each player for a contract of this magnitude? I believe it does.

As discussed earlier, both the Phillies and White Sox have significant payroll capacity below the luxury tax threshold to sign either Harper or Machado without threatening this number. In fact, each team could likely sign both players without approaching it. For example, the White Sox, even with recent additions Yonder Alonso and Ivan Nova, have less than $36 million committed in 2019, not counting arbitration-eligible players (the White Sox figure to approach $55-60 million after paying arbitration-eligible players).

Signing both Harper and Machado to 10 year deals in the $375 million range would result in a 2019 payroll in the $140 million range, well below the luxury tax threshold of $206 million for 2019.

As for the submarines, the Yankees have significant payroll capacity despite inheriting the previously mentioned contract of Giancarlo Stanton, whom they traded for last year, due to an otherwise relatively young and inexpensive roster.

The Dodgers, on the other hand, have pre-arbitration commitments near $150 million for 2019, and have gone on record in a document prepared for investors stating that they plan to stay below the luxury tax threshold through 2022. Adding a player such as Harper would likely push the Dodgers right up against this threshold, barring any significant reductions in their payroll as a result of trades.

Finally, the Cubs. While they are rumored to be one of Harper’s preferred destinations, they have pre-arbitration commitments for 2019 of $167 million, with Kris Bryant, Kyle Hendricks and Javier Baez expected to raise that number by $20 million or so. Adding Harper would push them over the luxury tax number for 2019, but more importantly, would set in motion a subset of other difficult decisions regarding their core position players, including the aforementioned Bryant, Baez, and Willson Contreras. Without an unforeseen offloading of a significantly salaried player, such as Jason Heyward or Yu Darvish, which seems incredibly unlikely, it just doesn’t make much sense for the Cubs to put their core at risk to add Harper to a roster that is widely expected to continue to compete for postseason births without him.

The Opt-Outs 

A reality of luring premier free agents is the necessity to provide the player with the ability to opt-out of the terms of his contract and to take another bite at the free agency apple. As both Harper and Machado are only 26, it is extremely likely that Scott Boras and Dan Lozano will be seeking an opt-out for their clients after their age 29 seasons.

While there is nothing magic about age 30, the allure of the option of hitting the market to capture an even larger payday prior to the big 3-0 will likely be too appealing to pass up. To guarantee even further flexibility, it would surprise no one if the agents also sought an additional opt-out beyond a year three opt-out, perhaps after year 5.

While the market may not be as generous for after their age 31 seasons, an opt-out will provide additional insurance to the player in the case that success eludes the team, or a particularly productive age 31 season.

Opt-outs will not be something pursuing teams will be fond of, but they are likely the price of playing poker. One strategy to deter the player from opting out is to make the years immediately following the opt-out provision particularly lucrative. Consider the table below, depicting one potential strategy to deter the player from opting out after year 3:

2019 2020 2021 OPT-OUT 2022 2023
$30m $30m $35m ——————- $50m $50m
OPT-OUT 2024 2025 2026 2027 2028
——————- $40m $35m $35m $30m $30m


Stacking the annual compensation in such a way may serve to dissuade the player from walking away from the most lucrative years of his deal. In this instance, a player opting out after year 3 would be walking away from not only two consecutive $50m annual salaries, but a total salary of some $270 million over 7 years, a tough deal to beat even as a 29 year-old hitting free agency.

Besides financial incentives to deter a player from opting out, it’s likely that teams may offer other innovative clauses to counteract a player’s ability to opt-out, should such an opt-out be provided.

Because much of the concern a player has when requesting the ability to opt-out of a long-term pact is centered around a) a more lucrative marketplace for his services; and/or b) the desire to exit a situation wherein success is eluding the organization, it’s possible that clauses might be put in place by the organization which could be triggered by certain events that essentially void the player’s ability to utilize his opt-out clause.

Potential conditions could be individual performance escalators which kick in if certain targets are reached, but also void an opt-out clause, or perhaps something more innovative still, such as postseason appearances or team payroll spending thresholds. Conditions such as these offer protection to the organization from being put in the awkward position of having a star player opt-out after just a few years of a long-term contract, while protecting the player against changing market conditions (or even new collective bargaining agreements) or projected team success simply not materializing.

The No Trade Clause 

No trade clauses have become fairly common requests for premier free agents in the last two decades, and in large part, organizations seem willing to concede them. This is in large part because players generally seem willing to waive a no trade clause to escape the type of situations that generally lead an organization to wish to trade them.

What a no trade clause can provide the player, however, is some level of control over which organization he is ultimately traded to, which in most cases is the more important right preserved by no trade clauses, rather than the ability to remain with the organization he initially contracted with.

A recent example is Giancarlo Stanton. When new Miami Marlins ownership determined it was in their best interests to move Stanton’s hefty contract off their payroll, they engaged in discussions with many teams, including the San Francisco Giants and St Louis Cardinals.

It was widely reported that Stanton, who had a full no trade clause, refused to waive the clause to facilitate a deal with either club. However, when the Yankees agreed to the framework of a deal with Miami, Stanton agreed to waive his no trade rights. While he had no desire to remain with a Marlins organization that had no desire to continue to build around him, he was able to utilize his no trade rights to control which team he would be traded to.

Another example is current Arizona Diamonback Zack Greinke, who reportedly has a limited no trade clause which includes fifteen major league clubs. While it is possible, should the Diamondbacks choose to move Greinke, that he could ultimately waive his no trade rights and accept a deal to a team currently on his limited no trade list, the clause protects him against being dealt against his wishes to what amounts to half the League.

A final word about no trade clauses: while they have become somewhat of a foregone conclusion in recent years in the contracts of premier free agents, notice that both Stanton, who holds the current record for total contract value, and Greinke, who holds the current record for average annual value, have either been traded already (in the case of Stanton), or are the subject of current trade rumors (as in the case of Greinke).

Signing a premier free agent may seem to point to an optimistic future for both player and organization, but unforeseen events can and do occur, often outside the control of either party, and thus, the parties must protect themselves appropriately when engaging in such significant agreements.

My Tea Leaf Predictions

Bryce Harper – Public speculation is that the Phillies and White Sox both have the desire and the ability to sign Bryce Harper to a record-breaking long-term contract, rumored to be anywhere between 10 and 12 years in duration.

Meanwhile, the Dodgers, Yankees and Cubs all appear to have interest, but either a lesser desire, or a lesser ability to land the superstar outfielder. Guessing Harper’s preferences are a bit more difficult. It is anticipated that he values off the field opportunities, proximity to his Las Vegas home, and an organization capable of sustained competitiveness. That being said, make no mistake, what Bryce Harper values the most with this contract – most likely to be the best opportunity to optimize on the field earnings of his career – is, you guessed it, money.

Experts and non-experts alike have been speculating for years as to just how much money Bryce Harper would receive in this free agency period. Projections have ranged from $250 million to $500 million. More recent expectations have narrowed that range to something between $300 million and $400 million.

Harper struggled a bit out of the gate in the first half of the season, and despite a better second half, it may have limited the top end range a bit. Additionally, with the fairly rapid shift to advanced analytics among Major League clubs, teams have increasingly better predictive models from which to value on-field contributions. While premier free agents will always elicit a larger difference of opinion regarding a player’s potential worth than more commonly available free agents, the industry has shifted to decision-making which relies significantly more on data than on emotion.

As mentioned previously, if we believe it is important to Harper and agent Scott Boras to eclipse both the total value record of $325 million set by Giancarlo Stanton, and the average annual value record of $34.2 million set by Zack Greinke, assuming a 10 year contract, it is likely the floor of any offer Harper might accept is 10 years, $345 million.

Such a floor all but eliminates the Chicago Cubs and the Los Angeles Dodgers – barring trading players earning significant salaries – due to financial constraints created by the luxury tax consequences of such an offering. Thus far, neither the Cubs, nor the Dodgers have been able to find a taker for some of their higher salaried players.

This is likely due to the fact that the very clubs with enough payroll capacity to entertain such a transaction also happen to be the clubs competing against them to sign Harper and/or Machado. Therefore, it is very unlikely that a team like the Phillies or White Sox, who might be interested in deploying capital if it were attached to talented cost-controlled young players, might entertain such a construct while Harper and Machado remain on the market.

That could change, however, if the Cubs or Dodgers threw caution to the wind and signed Bryce Harper or Manny Machado prior to moving some of their higher salaried players. While this would likely remove some of the Cubs or Dodgers’ leverage, it is possible that teams missing out on the megastar free agents might see such a trade as a worthwhile manner in which to deploy their capital.

While the Yankees could potentially offer such a contract to Harper, they currently don’t have the roster flexibility to play Harper in the OF, and the idea of the two parties agreeing to such a lucrative deal to fill first base seems far-fetched. All of Yankee GM Brian Cashman’s public comments support such speculation.

As stated above, this leaves the White Sox and the Phillies as the two parties in the best position to offer Bryce Harper the kind of record-breaking long-term deal he and agent Scott Boras will demand. While the Phillies have more payroll commitments on the books than the White Sox, the practical difference is fairly irrelevant. Each team has the payroll capacity to offer Harper well above the current 10 year, $345 million contract required to eclipse Stanton and Greinke’s milestones. So, what gives?

It is this author’s contention that the White Sox find themselves in a better position here than the Phillies, for several reasons. First, the Phillies, while they would love to have Harper, are said to prefer Machado, due to positional need. Unless Machado were to sign before Harper, with a team other than the White Sox, it is likely the Phillies will prioritize Machado over Harper.

Second, the Phillies play in the same division as Harper’s previous team, the Washington Nationals. While plenty of players have gone on to play for divisional rivals, it requires the player to frequently revisit his previous stomping grounds, exposing him to booing, taunting, etc. It is unlikely that this is a nonstarter for Harper, but it simply may not be his preference. Third, Philadelphia is nowhere close to Harper’s hometown of Las Vegas. Again, not likely a deal-breaker, but another minor strike against the Phillies.

One thing the Phillies have going for them that the White Sox do not, is the win-loss record. The Phillies won 80 games in 2018, and are likely at least one year ahead of the White Sox in regards to reaching a truly competitive window. They’ve only added to their lead this offseason, trading for Jean Segura and signing Andrew McCutchen. While they did lose Carlos Santana, they will simply move Rhys Hoskins to 1B and slide McCutchen into the outfield spot vacated by Hoskins. And yet, despite this recent success, the Phillies stumbled badly down the stretch, and had the second worst record in baseball after August 7th.

The White Sox, on the other hand, have a number of their own shortcomings to overcome in any pursuit of one of Major League Baseball’s brightest stars. First, and most obvious, is their spectacular failure over the previous two seasons.

While much of this was by design, as nearly every player of any consequence was shipped off for future returns of prospects and salary relief, it is widely believed that even the White Sox front office was surprised that the team lost 100 games in 2018.

Second, the White Sox are not even the most popular team in their own city. The Cubs have dominated the city in recent years, particularly since arising from the ashes of their own rebuild and reaching four consecutive postseasons, including their first World Series title in more than 100 years in 2016.

While Chicago still has all the allure of one of the nation’s premier cities, the White Sox’s secondary status seems to almost diminish them as a destination even for players not being pursued by the Cubs.

Third, the White Sox, despite winning a World Series (2005) more recently than more than half the League’s teams, have not qualified for the postseason since 2008 and lack much of a winning tradition that any twenty-six year old would recognize.

So what advantages do the White Sox have over the Phillies again? In their pursuit of Harper, I believe there are many.

First, despite their secondary status in their own city, Chicago is still Chicago. It is a larger market than Philadelphia, with a significantly larger population, with fewer competing major markets in the direct vicinity. It has one of the richest cultural and sports histories of any city in the United States. Other than perhaps New York City and Los Angeles, Chicago provides an opportunity for an athlete to build a brand that other major cities simply cannot match. Just ask the world’s most popular athlete of all time, Michael Jordan.

Second, despite the White Sox’ 62-100 record in 2018, they have an attractive future to sell. While the Phillies may have more pieces in place on their Major League roster, the White Sox have a number of potential all-stars waiting in the wings. First among them is Eloy Jimenez, the 3rd ranked prospect in all of baseball. Not far behind Jimenez is Dylan Cease, widely regarded as one of the best starting pitchers in minor league baseball, and recent recipient of MLB Pipeline’s Pitcher of the Year award.

Behind Cease, the White Sox feature a number of other high-ceiling prospects, among them Luis Robert, Nick Madrigal, and Zack Collins. The White Sox system is not simply top-heavy either; there are as many as 15 projected Major League regulars among their top 30 prospects. The Sox also have a number of young players that have reached the big league club that show significant promise. Among them are Yoan Moncada, Tim Anderson, and recent Tommy John recipient Michael Kopech.

While choosing the White Sox would require some faith on the part of Bryce Harper, they are on a similar trajectory as recent World Series winners in the Chicago Cubs and Houston Astros.

Third, the Kris Bryant effect. Bryant is one of Harper’s best friends, as they grew up together in Las Vegas. While it is likely that Bryant and Harper always dreamed of playing on the same big league club together, perhaps starting for opposite teams in the same major city is a nice consolation prize? We shall find out.

Fourth, and this may seem curious at first (stay with me here), is the White Sox’ recent  acquisition of Cleveland Indians’ first baseman/designated hitter Yonder Alonso, who also happens to be the brother-in-law of Manny Machado. How does the White Sox’s acquisition of Manny Machado’s brother-in-law help them acquire Bryce Harper? Well, it provides the White Sox with something other teams pursuing Machado do not have – one of his best friends – and someone Machado looks up to immensely.

The prospect of the White Sox having an inside track on Machado may force Harper and Boras’ hand out of concern that should the Sox sign Machado and fall out of the market, he could be left without negotiating leverage with Philadelphia. Therefore, Harper may choose to preempt a potential White Sox signing of Machado by signing with the Sox himself.

So where does Bryce Harper ultimately choose to sign what will likely be the largest contract in the history of Major League Baseball? I believe the stars will align with Bryce Harper and the Chicago White Sox. The Dodgers, with their pedigree, proximity, and star power, will provide temptation to Harper to take less money and less years, but ultimately they will come up short.

Boras and Harper will simply not be willing to take the type of haircut necessary for him to land in la la land. That being said, Boras will absolutely use the specter of the Dodgers to make the White Sox and Phillies offer a significantly more lucrative framework than that of LA.

If both teams do so, Boras will pit the two against one another in a game of high stakes poker. This is again where Manny Machado has the ability to affect the Harper bidding. Machado, as mentioned above, is believed to be preferred by the Phillies, and it would not be surprising if they back down at some point to refocus their efforts on the infielder. That, combined with some speculation that Harper isn’t particularly interested in Philadelphia, may be what ultimately delivers Harper to the White Sox.

My prediction on Harper: White Sox, 10-years, $375 million, opt-outs after years 3 and 5, full no-trade clause, perhaps with some innovative clauses built-in to provide protection to the club against the opt-outs.

Manny Machado – The Manny Machado free agent tour begins on Monday, December 17, as he officially visits the White Sox. Agent Dan Lozano, as well as Jon Heyman, claim there are six teams seriously interested in Machado’s services: the Yankees, Phillies and White Sox, as well as three (say it with me) “mystery teams.” It is unknown whether these three mystery teams actually exist, or are an effort by Lozano to expand the market for his superstar client. Mystery teams notwithstanding, the visits for the three named teams will occur the week of December 17-21, wrapping up in Philadelphia on Thursday the 20th.  

Machado is known to have an affinity for the Yankees, and except for the speculation that Hal Steinbrenner won’t authorize Brian Cashman to offer a record-breaking contract to Machado that beats current Yankee Giancarlo Stanton, they would undoubtedly be the heavy favorite. However Steinbrenner was vocal in his criticism of Machado’s “Johnny Hustle” comments in the wake of his strange behavior during the Dodger’s postseason series’ with both the Brewers and the Red Sox.

Additionally, the Yankees, as mentioned above, already have the League’s largest contract on their payroll, as well as players on their existing roster (despite Didi Gregorious recovery from Tommy John surgery, which will result in a late return for him in the ’19 season) to fill out the left side of their infield. It is simply unknown whether the Yankees will determine it is in their best interests to ink Machado to a record-breaking long-term contract.

The White Sox also have interest in Machado, despite some believing their true preference is Harper. They have been searching for a decade or more for an above-average player to take the reins at third base, and also appreciate Machado’s star power. To be fair, Machado has long been the more likely opportunity to land a premier free agent, however, the smaller than expected Harper market caused the White Sox to dream big and go for broke.

That being said, even should they miss on Harper, Machado would be one hell of a consolation prize. Secondary target or not, the White Sox have not hidden their desire to attract Machado. In a statement that speaks on its own to anyone not hiding under a rock (as mentioned above), the Sox went as far as to acquire Machado’s brother-in-law Yonder Alonso, who is known to be very close with the him. Should the Yankees determine it is not in their best interests to shell out the kind of cash necessary to compete with the White Sox and Phillies, the White Sox might have an edge over the Phillies through their acquisition of his close friend and mentor, Alonso.

We should not overlook the Phillies when it comes to Machado. The Philadelphia brass, including Andy McPhail and Matt Klentak, were with the Orioles front office when Baltimore drafted Machado 3rd overall in the 2010 First-Year Player draft. It is likely that the same front office that drafted the player would very much like to sign the player, particularly since both McPhail and Klentak departed Baltimore prior to Machado reaching the big league club in 2012 and progressing on to superstardom.

Additionally, as noted previously, the Phillies are the benefactor of a 25-year, $5 billion television contract, and thus, whether one truly believes ownership’s comments regarding spending “stupid” money or not, they are in prime position to deploy some of those riches to engage Machado’s services for many years to come.

Missing out on both Harper and Machado, despite their significant payroll capacity, would be a significant swing and miss for the Phillies, and potentially negate the step forward taken by the franchise in 2018. There are 350 million or more reasons to believe they will go all out to land at least one of Harper and Machado, with Machado being the more likely acquisition.

As the negotiations play out during and shortly after Machado’s free agent tour, it’s likely to be portrayed as the Yankees’ mystique, versus the White Sox family connection, against the Phillies’ “stupid money.” Critical to this dynamic is whether Bryce Harper decides to wait out Machado’s decision, or if he takes the plunge and signs with the Dodgers, Phillies or White Sox before Machado.

Personally, I believe Harper may very well wish to avoid a game of musical chairs in which he must choose between a team less to his liking and a team offering significantly less years and money. As a result, I believe we see Harper signing with the White Sox, prior to Machado making his decision, in an attempt to avoid this scenario. While we cannot guarantee the White Sox would fall out of the Machado market in this instance, and there are some signs that they might not, it still remains unlikely that after committing to the largest contract in Major League Baseball history, that they would still have the resolve to outbid Philadelphia on Machado.

This would set in motion a choice for Machado between his heart and his mind. The allure and mystique of the Yankees versus the familiar Phillies’ front office and their pockets bulging with television revenue.

My prediction on Machado: Phillies, 10-years, $375 million, opt-outs after 3 and 5 years, full no-trade clause.

You can follow Mark on Twitter at @iamshack24



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