One of the biggest free agents on the market – Manny Machado – has reportedly agreed to a 10-year, $300M deal with the San Diego Padres as first reported by Jeff Passan. This ends a long saga that saw the Padres enter the sweepstakes late and most not giving them much of a chance to sign the generational talent who is just 26 years old.

As the Padres are my second team after living in San Diego for my college years and another 10 years after that – this is great news for the team. This confirms that the Eric Hosmer signing was indeed their Jayson Werth Moment – a moment that transformed the Nationals from the perennial losers they had been as the Expos for the previous two decades into the annual powerhouse they have been since.

My 3 key takeaways from this deal are as follows:

1. The money is really not that big a deal. In fact, the Padres might have gotten a bargain.
2. The length is not that big of a deal either.
3. With a couple of pitching additions, the Padres can be competitive every season starting in 2020.

Let’s dig into the first one: the money. Yes, it is a lot and big flashy round numbers. 10 years and $300M. That comes out to about $30M a season. In 2018 Clayton Kershaw was the highest paid player in Major League Baseball at nearly $36M, followed by Mike Trout just north of $34M, Zack Greinke at $34M, Miguel Cabrera, David Price, Jake Arrieta, and Albert Pujols at $30M. According to Spotrac and their Best Value Ranking, only Mike Trout is worth it.

The concern I do have about the money is how it might hamper future needs for the Padres. Their payroll entering Tuesday was at about $75M. Machado pushes that over $100M and no team has ever won a World Series with one player taking up 30% of their payroll.

Wait – there is more. Kevin Acee wrote this great article back in January about how the Padres current ownership inherited a lot of debt and worse debt deals from the previous ownership group after a failed sale to Jeff Moorad. In a fashion that only Padres fans could nod their heads and say, “Yep”, the Padres have been chipping away at that debt with about 8% of the annual revenue. Furthermore, after a splurge of signing and trades in the winter of 2014 – nearly ALL of which failed – the Padres still owe players long gone – but that phase is nearly done. The most egregious example is Hector Olivera, who was part of the trade that sent Matt Kemp to the Braves after they got him from the Dodgers but faced domestic abuse charges. He is owed $7.5M from the Padres in 2019. Yet Acee points out a key fact:

In 2019 and 2020, the Padres are on the hook for a net of $28.75 million payable to players no longer with the team. That number shrinks to $8.5 million in ’20 and to zero afterward, giving the Padres further financial flexibility — or money to spend on players that will actually play for them.

Enter Manny Machado. Ten years though?

Ten years is a long time, but Cliff Corcoran of The Athletic did a great piece about the actual history of 10-year contracts in MLB history. We tend to remember the ones that turned out really badly thanks to the availability heuristic – like when we hear about a plane crash and think our next flight is doomed. There have been just 7 10-year free agency contracts (now 8), and 7 players have signed extensions of 7 years or more, though only four of those were a single contract and not a second re-up. So for example, both Giancarlo Stanton’s and A-Rod’s contracts were technically extensions or restructuring of current contracts, not brand new contracts like Machado’s. Stanton, of course, is in a 13-year, $325M contract and A-Rod opted out of his original Rangers contract for a 10-year, $275M contract.

Yet Dave Winfield signed a 10-year deal with the Yankees which, disagreements with George Steinbrenner aside, worked out pretty well. A-Rod’s original deal with the Rangers actually worked out well, as well as a 10-year extension for Derek Jeter with the Yankees and some restructuring the Rockies did with Todd Helton.

It is easy to point out the 10-year deal of Ryan Braun and Albert Pujols – but those were not given at 26 years old with 5 solid seasons of performance. Corcoran ends his examination much more poetically than I could myself, so he has this to say:

Yes, the surest way to be right is to predict failure. The universe trends toward entropy. Eventually, the naysayers will be proven correct. However, to build a winner, teams have to bet against entropy with real money. That’s why it’s hard. That’s also why it’s fun. Because winning is the act of dodging inevitable failure, of postponing inescapable decay. It’s temporary, but it’s exhilarating, and teams can’t do it by hoarding their money. Bryce Harper and Manny Machado are two of the most compelling free agents to hit the market in years. They’re young, they’re talented, and they will help their new teams win. All those teams have to do is pay them.

My final point is for those that are saying Machado doesn’t care about winning…only the money. First of all, the Padres really do have some exciting prospects at or near the major league level, including 2nd ranked (in some places first) overall prospect Fernando Tatis Jr. You can question what good prospects are until proven performers, but the team is closer than most would think looking from afar. Joey Lucchesi, Eric Lauer, and Robbie Erlin form a nice young trio that with some growth can keep their team competitive. Mackenzie Gore, Chris Paddack, Cal Quantrill, and others are the future of his ball club. This team really needs another strong starting pitcher or two – but with their prospect depth, the team can use that depth in trades likely next winter heading into 2020.

The National League West is also in shambles. The Giants are in full rebuild mode (unless they sign Bryce Harper?), the D’backs are rebuilding, and the Rockies have one more season guaranteed of Nolan Arenado. The Dodgers will always be strong – but after back to back World Series losses you have to wonder what that does to their psyche? Not to mention the fact that they only won the West last year thanks to a win in Game 163. By all measures, they under-performed where they “should” have been, but will certainly be the Padres nemesis for the foreseeable future.