The Phillies left the winter meetings with a bolstered outfield, both offensively and defensively, with the addition of Andrew McCutchen and the removal of Rhys Hoskins from the outfield, and they came into the winter meetings with a bolstered infield, offensively and defensively, through the addition of Jean Segura and the return of Rhys Hoskins back to his natural position at first base.

For a team that was in first place for most of the season, that's a good start. It isn't, however, bagging one of the white whales on the Free Agent market that immediately improves the team by something like 5 wins all by themselves.

There are two players still available who can do that, and after managing partner John Middleton's comments about spending "stupid money" this offseason, it would quite frankly be disappointing if the Phillies were to enter next season without having signed one of those two players. In fact, the structure of McCutchen's deal, being backloaded with only $10M committed for 2019 makes it seem as if they're keeping some powder dry for some sort of big signing.

And make no mistake, after a few seasons of running pared down payrolls, in a league where basically every team is making something like $100,000,000 after national and local television revenues, MLBAM share, merchandise, gate, concessions, etc, the Phillies have money to spend. In fact, the Phillies are likely running annual incomes much higher than that $100M estimate, especially considering their partial stake in NBC Sports Philadelphia, which benefits when other local teams like the Flyers (made the playoffs in 2017-18), 76ers (have an exciting young team and made the playoffs in 2017-18), and Eagles (won Superbowl 52, defeating the New England Patriots by a score of 41-33) experience success. Also, John Middleton is worth an estimated $3.2 billion dollars.

So, with gobs of money to spend, how does one land a marquee free agent, in their prime, in the Year of Our Lord 2018/19? Like so:

Season Salary 2019 $60,000,000 2020 $45,000,000 2021 $20,000,000 2022 $30,000,000 ~~Opt Out~~ 2022 $35,000,000 2023 $35,000,000 2023 $20,000,000 ~~Opt Out~~ 2024 $25,000,000 2025 $25,000,000 2026 $25,000,000 2027 $25,000,000

Total: 10 years, $345,000,000.

For practical purposes assume that first year $60 million dollar figure is a combination of signing bonus and salary.

Reasoning:

First, you cover three basics. The player gets bragging rights to the largest contract in Major League Baseball History, the highest average annual value/cap hit in MLB history, and to the highest single-season salary in baseball history. Whether or not they play out those years after the opt-outs is irrelevant. Players and agents are ultra competitive and this checks two of those boxes easily, establishing bragging rights for all parties involved. Also, it's just a whole lot of money going to both of those parties.

Second, you're looking at what is essentially a 4-year, $155 million dollar contract that covers the prime of an elite players career, with an optional 3-year, $90 million dollar extension. Would you do a 4/$155M deal for an elite player at age 26? I don't think there's any question that's not only reasonable, but a bargain. If they're hugely successful, youi've gotten 4 years of an elite talent at a discount. If they're moderately successful they're a bit more likely to accept the 3/$90M option, so now you've got 7 years of All-Star calibre performance, if not MVP calibre performance, for $245M, or a $35M annual cost through age 32. Not too bad.

Third, structure. The deal is structured to allow flexibility for both the player and the team. For the player, you're giving them two options to abandon the deal and re-test free agency, which is obvioulsy player-friendly, and par for the course when it comes to deals for elite players today. In fact, you're giving the player more options, because as far as I know, this would be the first two-opt-out contract in baseball. Second, the first opt-out is a year into the new CBA, which is allows the team some stability entering the new bargaining agreement era, but also allows the player to explore free agency options in the event the new agreement massively changes the landscape in favor of free agent players. Third, the structure of those first four years allows for the possibility that the team can offer a future free agent, say, for example, someone coming to free agency in 2021, the exact same type of deal I just proposed here--a huge number in 2021, staggered salaries thereafter, moderating the yearly team expenditures and the AAV of the contract for luxury tax purposes.

It's not my money, so it's easy to propose this, but on the other hand, if you spent the last year talking about your desire to win, and do so by spending "stupid money" well, this is what it's going to take, in my estimation. At the end of the day the player has the leverage, and can go wherever they like, and also has the ability to play teams against one another, and there's really nothing the Phillies or Middleton can do about that. What they can do, however, is wow the hell out of either of the guys they're targeting and make them an offer that is very, very difficult to turn down, and painful for other teams with significant standing salary commitments to match, which, again, I think this deal accomplishes.

Feel free to cc this post to Matt Klentak if you happen to be a friend of his, or if you happen to be Bryce Harper, Manny Machado, Scott Boras, Dan Lozano or any friend/acquaintance thereof. My consulting fees are more than reasonable.