David Robertson is having an odd winter

It’s not every day that a man becomes a meme. In order to turn a moment in time into an ongoing joke, you need the perfect recipe of a funny reaction, a great camera angle, and enough interest in the scenario for people to create significant chatter. David Robertson was able to accomplish that feat last October with a deflected pitch.

In the sixth inning of the 2017 Wild Card Game against the Minnesota Twins, Robertson’s pitch was tipped right into Gary Sanchez’s...nether regions. All of the powers of empathy inside of the Yankee reliever came bursting out at once, giving the internet a hilarious visual.

He can be quite expressive on the mound, but what’s interesting is that this timeless photo of a man cringing in reactive pain seems to encapsulate Robertson’s bizarre offseason to this point.

Back in October, Robertson fired his agent Scott Leventhal. There was no public reason for the parting of ways, but it’s an interesting move given his last contract. In a stint with the White Sox before coming back to New York, the reliever landed a four-year, $46 million deal. For a bullpen arm, that’s big money.

Now, entering his 12th season in the majors and on the back nine of his career at 33, Robertson has to negotiate the free agent market on his own for the first time. He’s seeking a three-year deal, according to MLB’s Mark Feinsand, which would take him through age 36. However, his confidence isn’t lacking. As he puts it:

I feel like I’m in my prime and I’m ready to go for another three years. We’re trying to just go with the flow. This is my first time representing myself, so I’m taking it slow and weighing my options.

D-Rob has reason to feel like he’s in his prime. He was a staple of the Yankee bullpen in 2018, going 8-3 with a 3.23 ERA. He also ranked 17th in the league in total strikeouts for relievers with 91 over 69.2 innings. Additionally, when Aroldis Chapman went to the disabled list after suffering a knee injury, Robertson was counted on in many high leverage situations for the Yankees. He’s thought of in the organization as a key asset, a trusted hand to help bridge the gap to their closer. Free agency agreements can be tricky, though, especially when off-the-field factors come into play.

An emerging controversy about a players-only meeting in St. Petersburg, Florida, at the end of the season has landed on Robertson. The meeting was to discuss postseason bonus shares. Players are paid for the games they play during the regular season, but not the postseason. For teams who make the playoffs, their players could possibly log up to a month of additional baseball for no pay, from a contractual standpoint.

To account for this, a players’ pool of money is created from the earnings from gate receipts at postseason games. Teams who play in more games, like the World Series champions, get a bigger pot to split than other teams, like a team who lost in the Wild Card Game. Each team gets 25 even shares of pay to split among active players.

The problem is that this pot doesn’t account for other members of the team, like bench players, players who were traded away, clubhouse employees, etc. So, traditionally, teams will hold players-only meetings to decide who they want to give shares to and how much they want to dilute their own earnings. In a league where players have multi-million dollar contracts and those receiving the minimum still make $545,000 per season, it would make sense that these shares are spread to everyone in the organization. After all, assistant coaches, analysts, drivers, and chefs certainly aren’t seeing the kind of money the players are seeing.

At the Yankee players’ meeting in Florida, Robertson held court as he’s been involved in representative meetings in the past. The vote resulted in assistant hitting coach, P.J. Pilittere, only getting a half share while a number of other support staff like Zac Fieroh, an analyst who normally travels with the team, received no shares. That’s a deviation from normal voting outcomes.

While no one knows exactly what went on in that room and Robertson and his one vote can’t fully be blamed for the fallout, as the one running the meeting, this isn’t a good look. Robertson, who runs the High Socks For Hope organization with his wife, Erin, has always had a good reputation in the league. However, this spat may leave a bad taste in the mouths of Yankee management come negotiation time. That might add a wrinkle for D-Rob who is flying solo in free agency for the first time.

So what’s the next move for Robertson after a strange start to his winter like this? In all honesty, not much. He wants to remain a Yankee but is looking for a solid contract. The Yankees want him back and have other holes to fill without having to worry about shoring up the bullpen. The two sides seem to want a deal but an issue could arise where Robertson thinks his numbers put him in the driver’s seat while the Yankees think the postseason share vote situation and their position as a top contender put them in the driver’s seat. A rookie representative may not have the sea legs to steer a ship through those waves.

Whether it helps his case or not, a sign of good faith for the organization would be for D-Rob to pull the team together to pay the non-player members their Wild Card and ALDS bonus money. Even without knowing the specifics of the voting decisions, it’s money the players can and should share. Robertson is a face that fans and players want to see in pinstripes. Hopefully he can fix this situation so that feeling is shared by everyone who makes the team run.