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  • Writer's pictureVillanova Sports Law Blog

Congrats Red Sox...Now Let's Talk Offseason

Updated: Feb 12

By Michael Horvath:

It is officially here, everyone: the offseason we have all been waiting for. If you are a Boston Red Sox fan, then congratulations on winning The Fall Classic; it was well-deserved. However, if you a Phillies fan like myself or a fan of any other MLB team that tends to make you suffer, then you have probably been focused on the 2018-2019 offseason. It is quite an exciting time as this offseason features one of the most anticipated free agent classes in modern baseball, accompanied by several first-year arbitration cases that call upon teams to hand-out large deals.

Three years ago, it was anticipated that this offseason would feature the most-talented free agent class in history. Clayton Kershaw was undoubtedly the best pitcher in baseball. Dallas Keuchel was a Cy Young Award winner and was an utterly dominant force in the Big Leagues. Matt Harvey was the ace pitcher of an absurdly strong Mets rotation, who lost in the 2015 World Series. Bryce Harper and Manny Machado were playing amazing baseball and had the fans speculating that either one could be the first player to sign a $400 million-dollar contract.

But that was three years ago, and in sports, three years is an eternity. Fast forward to 2018 and it seems that the only thing that still holds true from that list is the prowess of Harper and Machado, players working on achieving “Legend Status,” despite some struggles from both this past season. The biggest disappointment for this off-season class has been the free agent starting pitchers. The Los Angeles Dodgers and Kershaw avoided free agency, agreeing to a three-year, ninety-three million dollar contract [1]. Kershaw is coming off his third straight injury-riddled season, and has demonstrated an anathema to winning big games. Harvey, who everyone thought could garner a huge contract this off-season, will be lucky to get a two-year deal. Harvey and Kershaw’s sudden fall from grace can be attributed to multiple injuries and subsequent drops in velocity for both pitchers. Cole Hamels and Keuchel round out what would have been a strong pitching class.

However, the spotlight remains on the position players entering free agency. The question looming throughout the Hot Stove Season: who will get the bigger deal? Machado or Harper? Despite a return to earth after the 2018 All-Star break, Machado remains the gem of the infield free agent class. Machado is expected to receive a massive deal, which could be up to seven years if he so choses, based on his outstanding career statistics and versatility in the infield. [2] Will Machado be the first $400 million-dollar contract in the MLB? While I think he will fall short of that mark, it is not off the table. Ultimately, it will depend on how aggressive teams like the Phillies or Giants are to get back in the playoffs in 2019.

In the outfield, everyone has their eye on Bryce Harper. Harper has been the backbone of the Washington Nationals since he stepped foot on the scene hitting a solid .279 with 184 home runs in his career. [3] The number one overall draft pick in 2010 is finally a free agent and can possibly be the first player to achieve the $400 million-dollar contract. Despite his 2019 first-half slump, Harper seemed to have pulled himself together after an electric Home Run Derby victory in Washington this past season. The Yankees, Phillies, and Nationals all have interest in bringing on Harper, but pursuing a contract as large as his will be no easy task for any team.

Outside of free agency, there is a strong class of young stars that will become eligible for first-year arbitration in January. Some notable first years include: Corey Seager (LAD;SS), Javier Baez (CHC;2B/SS), Francisco Lindor (CLE;SS), and Aaron Nola (PHI;P) to name a few. These players, along with their agents, will complete their player filings under Article VI, Section E, Part 10 (a) & (b) of the CBA by January 12th. [4] The respective teams will then file their numbers on January 16th. [5] Afterwards, the two parties will have until February 1st to negotiate and avoid arbitration. [6] If no agreement is met, a three-person arbitration panel will hold hearings to settle the issue. Although actual arbitration hearings are becoming less common, it would not be surprising to see several first-year players end up in front of the panel, especially considering the talent in this class.

This off-season alone, the Chicago Cubs have four players who are arbitration eligible for the first time (Baez, Schwarber, Montogmery, and Edwards). While the Cubs seem to have a more complete roster right now, it will still be interesting to see how they handle negotiating all of their arbitration cases and attempt to remain under the MLB luxury tax. I would not be shocked to see one, if not more, Cubs players in a hearing come February.

The Yankees also have their hands full. Luis Severino, Greg Bird, and Ronald Torreyes will all be entering first-year arbitration in 2019. The Yankees face a major financial burden. They face several veteran arbitrations this year, several highly-touted free agents to potentially re-sign, and they are pursuing outside free agents, like Bryce Harper. With a hefty amount of salaries to pay in 2019, it wouldn’t be out of the ordinary for the Yankees to be stubborn in their player filings, which could lead to some interesting panel hearings on their end too.

As you can tell, we have a lot going on this off-season. Three years ago, we expected this to be a wild year for free agency and arbitration. Injuries, disappointing on-field performances, and other mishaps have calmed down the hype, but I still believe that we should expect several eye-popping contracts and a decent amount of arbitration hearings this year. Make your predictions now, because the storm is coming soon.

[1]: Gonzalez, Alden. “Clayton Kershaw: New deal gives me chance to prove people wrong.”, 3 Nov. 2018,

[2]: Karraker, Patrick. “Previewing the 2018-2019 MLB Free Agent Class.” MLB Daily Dish, MLB Daily Dish, 7 Sept. 2018,

[3]: Id.

[4]: Sievert, Justin. “Breaking down the MLB Salary Arbitration Process.” Sporting News, 13 Jan. 2018,

[5]: Id.

[6]: Id.

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