The Yankees have experienced all the highs and lows, of draft compensation

After six seasons of service time, MLB players get a chance to hit the free agent market without restriction. This stands in contrast to leagues like the NFL and NBA, which offer teams the chance to unilaterally decide to keep the player with the use of the franchise tag or by matching contracts in restricted free agency.

The only aspect of free agency that may resemble some form of restriction is the draft pick that a signing team must forfeit when acquiring a player that has a received a qualifying offer. The system of draft-pick compensation has existed in many forms in MLB, but the foundation of the system is simple: a team that signs a great player often has to forfeit a compensation pick, while the team that loses said player adds a compensation pick to its coffers.

The risk-reward calculation favors the proven commodity of an established big leaguer, and that’s specially true under the latest CBA, which made it so only the signing upper echelon players cost high draft picks. That said, the Yankees’ experience with compensation picks in recent years illustrates the wide range of outcomes that are possible with the system.

In fact, only a quick glance at a two-year period in the mid 2010’s involving the Yankees can serve as an example of the varied impact this whole exchange can have on teams for years to come. Let’s take a look.

The Best-case scenario

Nick Swisher found himself in the Bronx at the beginning of the 2009 season after a miserable one-year stint in the south side of Chicago. The former Oakland A’s first round pick played arguably his best baseball in pinstripes, with a very successful four-year run in the Bronx.

After 2012, Swisher entered free agency and ultimately signed with Cleveland. That move granted his former team the 32nd pick overall in the compensatory round of the 2013 MLB Draft. That pick was used to draft Aaron Judge, a player you made have heard of.

Even Nick Swisher himself would probably admit that this turned out pretty well for GM Brian Cashman, and for a team not known to spend big like the now-Guardians, this outcome must sting a bit, even if there’s no guarantee Cleveland would have picked Judge if they were in position to do so. To date, Judge has hit 144 home runs as a Yankee, and has a career 148 OPS+ across six seasons.

The Good-case scenario

Rafael Soriano had a successful two-year tenure with the Yankees, tossing 107 Innings to the tune of a 145 ERA+. He joined the team after one year with the Rays without a comp pick tag slapped on him, but left with one attached.

The departure of the Dominican reliever to the Washington Nationals netted Cashman his second pick in the compensatory round of the 2013 MLB Draft, the 33rd overall. That pick was used to draft a high school pitcher, Ian Clarkin. While the left-hander out of San Diego never reached the majors he was a part of an important trade in 2017 that sent him, Tyler Clippard, and Blake Rutherford to the Chicago White Sox for Todd Frazier, David Robertson, and Tommy Kahnle.

Each one of those players had a significant impact for New York on their road to coming just one game shy of the American League pennant.

The other Good-case scenario

Before the 2014 season, the Yankees decided to really bolster their major league roster, and one of their biggest signings was that of Braves catcher, Brian McCann.

The left-handed slugger moved to New York and the Braves received a compensation pick, oddly enough the 32nd overall as well, and they selected a high school left-hander out of North Carolina, Braxton Davidson.

Davidson currently pitches for the Schaumburg Boomers in the Frontier League and Brian McCann went on to post 8.2 fWAR over a three year period in New York. A pretty good mark, even if he was never the same hitter as he was with the Braves. This simple demonstrates how teams that forfeit picks can often don’t feel any sort of sting in doing so.

Bad-case scenario:

Another significant signing during that 2014 season was the three-year deal for 37-year-old Carlos Beltrán. Subsequently. the St. Louis Cardinals used the 34th pick overall of the 2014 MLB Draft, received as compensation, to draft current ace Jack Flaherty.

Beltrán was actually productive in the Bronx, to the point where the ball club was able to flip him to Texas at the 2016 trade deadline for a prospect package. Although the minor leaguers never really panned out, they represented useful farm system depth at the time. Later on, their presence came in handy when the Yankees used acquisitions Dillon Tate and Erik Swanson as parts of the Zack Britton and James Paxton deals. That said, just as the McCann signing showcased one of the many times when draft picks and prospects don’t pan out, Flaherty’s ascension certainly worked to the Cardinals’ favor.

Worst-case scenario:

What happens when you sign a player you shouldn’t, and forfeit a pick that ends up being a key part of a rival’s success?

Ask the Yankees.

Beltrán and McCann received great paydays, but not on the same level as Jacoby Ellsbury. The center fielder made the switch from Boston to New York after accepting a seven-year, $153 million dollar deal.

Ellsbury could barely stay healthy for a little over the half of his contract, and fell off a cliff performance-wise after his initial season in New York. He never played again after 2017, and left hip surgery in early 2019 effectively ended his career.

As if that wasn’t enough, the Boston Red Sox received the 32nd overall pick in retur,n used to draft a high school right-hander by the name of Michael Kopech. Kopech kept improving as a prospect and wound up being an integral part of the Chris Sale trade alongside Yoán Moncada.

Sale is in line to make his 2021 debut tomorrow after missing significant time due to injury. If you happen to find yourself seeing any part of that game — or perhaps glimpsing the 2018 World Series banner at Fenway — remember that it all began with Jacoby Ellsbury.

As a final note, I cannot stress enough the fact that compensation picks don’t (or shouldn’t) come heavily into play when a team like the Yankees is deciding to invest in free agency. In the end, it’s mostly just interesting to trace transaction trees all the way back to their roots. It’s fascinating to see all the twists and turns that can occur, all starting with a simple little piece of draft compensation.