Can the Cincinnati Reds pry Mookie Betts or Xander Bogaerts from the Boston Red Sox?

You won’t find a single Top 100 prospect list that features young Average Annual-Value. Despite its reputation and aura growing by the year, AAV doesn’t seem to get the same recognition as the likes of Jeter Downs, or Hunter Greene, or Cristian Pache when it comes to accurately assessing importance to a team’s planning.

Dumb metaphors aside, AAV has become something that an increasing number of teams have to focus on this time of year, as the luxury tax in baseball becomes increasingly cap-like to the teams who spend more than their peers. Just last year, the Cincinnati Reds were able to leverage that in their massive deal with the Los Angeles Dodgers, a club who was trying to shed salary to avoid excess luxury tax payments themselves. The Reds improved their roster by taking the likes of Yasiel Puig, Alex Wood, and Kyle Farmer, but one of the key cruxes of the blockbuster was the move of Homer Bailey for Matt Kemp - due in large part to Bailey’s AAV hit being slightly lower than Kemp’s for LA’s bottom line. The deal cost the Reds Downs and Josiah Gray, a pair of prospects who improved their status greatly in 2019, but it brought light to a market that hasn’t really existed in the baseball landscape before.

It showed that clubs with payrolls nowhere near the luxury tax level can help bail out their peers who are facing that penalty. In essence, it opened up a way for mid-payroll teams to exert almost the same kind of advantage that the big-spending teams used to push their payrolls to the limits in the first place: increased spending potential, thanks to the mere power of having their level of spending not be taxed. A charitable donation, if you will, to help LA skip down a tax bracket.

The merits of the Dodgers/Reds deal can be discussed and broken down in another space, but the fact remains that the Reds basically helped the Dodgers skirt their would-be tax penalty by taking on their expensive veterans. It was a strategy we’ve not really seen from any other mid-market team in such a notable fashion, but is one that certainly could still be employed by the Reds, or any of their spending peers, again this winter.

The team most likely to play the role the Dodgers played last year, you ask? Well, it that sure looks more and more like the Boston Red Sox, the 2018 World Series champs who already parted ways with former GM Dave Dombrowski in 2019, in part because of how their payroll had skyrocketed while their farm system dried up.

As Michael DePrisco noted for NBS Sports Boston back in September, the Sox will end up paying some $13 million in tax penalties for their payroll excess in 2019, and it appears more and more that they’d prefer to not get hit with that kind of levy again in 2020. That will take some serious financial juggling, since Boston already has a projected payroll of some ~$230 million for 2020 - both on the books already and with the estimates for their fleet of high profile arbitration-eligible players - and is coming off a season where they clearly showed their roster still needs massive improvement to compete with the likes of Houston and the Yankees. In other words, for them to have any shot at dipping down below the tax threshold, they’re going to have to move a pile of salary to do so while still trying to get better, which is a very tough concept to pull off.

The Sporting News picked up on that in detail just over a month ago, as Tom Gatto outlined the ways in which the Red Sox could possibly shed enough salary to dodge the tax penalty. And if you’re a Reds fan looking for the club to up their payroll to bring in established stars in some form or fashion, seeing the likes of Mookie Betts, J.D. Ramirez, Chris Sale, and Xander Bogaerts floated as potential movers should certainly pique your interests.

From the Cincinnati angle, it’s going to be interesting to see exactly how 2020 centric their ambitions are in this aggressive winter. Obviously, their mid-2019 pickup of Trevor Bauer (at the cost of top prospect Taylor Trammell) suggested that 2020 is a hyperfocus, as Bauer is set to be a free agent at the end of 2020. So, too, is Betts, and with a projected salary of some $27 million stands out as both the single best potential acquisition and the most short term of the Red Sox stars, a tough combo for a Reds team that would still have to give up a prized package to land him. The inverse of Betts is likely Bogaerts, the 27 year old star shortstop who is controlled potentially through the 2026 season, but comes with up to $140 million owed his way for those services.

Reds President of Baseball Operations Dick Williams has gone on record saying that he expects the team to have ‘more financial resources at our disposal’ for 2020, as he told The Enquirer’s Bobby Nightengale in October, but the question obviously becomes to what level? Is it possible to think that in order to land Bogaerts, for instance, that the Reds could also take on, say, David Price and the $96 million he’s owed through the 2022 season, too? That would add a blistering $52 million to the team’s 2020 payroll alone, though it would fill a gaping hole at SS while also reuniting Price with pitching coach Derek Johnson as part of the burgeoning Reds/Vanderbilt concoction brewing in Cincinnati. The idea would also certainly have to feature a few financial makeweights like Kevin Gausman (~$10.6 million), Freddy Galvis ($5.5 million), or even Jose Peraza ($3.6 million) going the other way along with a reasonably touted prospect to slightly lessen the burden while still bailing out Boston, but it’s certainly a concept that would seem to fit the mold of how the Reds and Dodgers did business this time last winter.

It all will come down to just how motivated the incredibly resourceful Boston ownership group is to save themselves a few million bucks, really. It seems odd on the surface that a cadre of billionaires who have hung nearly a fistful of banners over the last decade and a half would be willing to shed so much talent to save 10, 12, 15 million bucks, but in firing Dombrowski and turning to Tampa expat Chaim Bloom and his concept of ‘sustainable competitiveness,’ it certainly feels as if that’s precisely what Boston has in mind both this winter and in the near future. And that, on paper, would certainly seem to dovetail well with a Reds club on the opposite end of the spectrum at the moment, one who is looking to pounce in the near term with the financial flexibility to pull it off, for once.

Maybe that’s Mookie Betts. Maybe that’s Xander Bogaerts. That Boston is even considering moving on from either is tantalizing as can be, but that the Reds seem to be quite well positioned to potentially be an ideal landing spot for either is the most tantalizing part of it all.