When Yankees second baseman and pending free agent Robinson Cano fired Scott Boras as his agent and replaced him with Jay-Z’s Roc Nation Sports and CAA, it was seen as a positive omen for Cano to stay with the Yankees. Gone were the predictions of a contentious negotiation with questions surrounding whether the Yankees would spend the money to meet the demands of Boras and Cano. The threat of the free-spending Dodgers was very real and Boras doesn’t care about team loyalty or legacy—he wants to get his players paid and the players hire him because they want to get paid. If it took a slow dance with the Dodgers or any other team to get the Yankees to put the ring on Cano’s finger, so be it. There’s no pretense nor is there ambiguity.
At first blush, the obvious response to the Jay-Z hiring was that Cano wants to stay with the Yankees. He dumped the agent who left the prospect of him re-signing in question, and hired someone who would facilitate a deal between the sides to avoid the mere possibility of a departure. Now, as time has passed and the contract talks between the sides at a reported impasse, it’s opening increased wonderment as to the wisdom of making the change. Boras wouldn’t have a deal done by now and would advise his client to go through to free agency. If the idea of hiring Jay-Z was to preclude free agency with a preemptive deal, well, that hasn’t happened either and doesn’t look like it will. So what was the point?
The Yankees payroll constraints are one reason that the long-term, huge money contract that Cano wants is not as guaranteed as it would’ve been five years ago, but there are others reasons as well. The Yankees need only look at the albatross that Alex Rodriguez’s contract has become; how Mark Teixeira’s contract is heading in the same direction; at Cano’s age (31 in October); how other players like Albert Pujols who have signed contracts similar to what Cano is going to want have declined, and set a line that they won’t surpass in terms of years or dollars hoping that Cano blinks. Are the Yankees going to be held hostage by Cano and Jay-Z for a ten-year contract and pay a 38-41-year old what will probably amount to 40% of the total value of the deal in those years when Cano will either be declining or finished entirely? It doesn’t help Cano that there is a lack of attractive options if the Yankees don’t want to pay. They’re not going to bid against themselves and they might play chicken with Cano as they did with Derek Jeter and tell him that if he thinks he can do better than their best offer, so be it.
Although Jay-Z has been certified as a player agent, the concept of him sitting across from Brian Cashman and poring through the contract’s fine print is silly. He’s lending his name to a new business and while he’s a savvy businessman, this “hands-on” concept won’t extend to the ludicrous with Jay-Z reading the fine print of a contract that is packed with legalese. While Jay-Z has qualified attorneys and agents handling the actual negotiations, this decision on the part of Cano reeked of panic, desperation and listening to the whispers of others. Changing agents so close to free agency and so soon after hiring Boras defeated the purpose of hiring Boras to begin with. Boras, in fact, never really did any contract negotiating for Cano; all he did was some saber rattling. It was a flighty and flaky move that could end up biting the second baseman and the rap mogul if they don’t get a deal done to the financial satisfaction of the player and the reputation of Jay-Z. And rest assured other agents who are threatened by Jay-Z’s foray into sports representation will latch onto any mistake, small or large, that is made and let players who are considering hiring Jay-Z know exactly what happens when they hire someone who’s not a legitimately experienced sports contract negotiator. Even though CAA is going to handle the contract nuts and bolts, many athletes will only see the end result if Cano winds up with less than the $250+ million he’s going to want or has to leave the Yankees due to overplaying his hand when his first (and probably only) desire is to stay.
When Cano fired Boras there was a sense—from me included—that the change was designed to turn down the rhetoric that was a part of Boras’s negotiating strategy and get something done to avoid even the threat that Cano would leave. But no deal has been struck and the Yankees are clearly going to wait to see what Cano and Jay-Z do after the season. Say what you want about Boras and the manner in which he does his deals, but his main interest is that of his clients. If they want money, that’s what he pursues; if they want to sign a down-the-line deal to stay with their preferred team as Jered Weaver did, he’ll acquiesce to their wishes.
With Jay-Z, Cano is a the test case in the expansion of an empire which tacitly indicates that the goals are not just for the player, but the representatives as well. In fact, Jay-Z might make be even more strident with the negotiations than Boras would to ensure that he’s not seen as a Yankees fan who had the power and sway to acquire a client the stature of Cano and allows that to blur the line between his client’s interests and his own. Whatever the intention was with the hiring, it hasn’t yielded any results as of yet and those results won’t be known until Cano’s fate is determined. That fate is currently up in the air just as it was with Boras, only there’s a different pilot who might not have the skills that the former pilot did. It makes me question the wisdom of changing planes in the first place.