Five years from now, it may prove the case that 10 minutes of utter chaos were responsible for determining the future shape of the Red Sox.
This year’s August 15 deadline to sign draft picks – or, more specifically, the deadline at 59 seconds past midnight on August 16 – featured a pressurized atmosphere akin to a boiler room. That was true for a number of clubs throughout the game, and it was most certainly the case for a Red Sox team that went down to the wire on six different negotiations with potential draftees.
This was no small matter. The Sox viewed this draft as a potentially pivotal one for the organization.
The team had parted ways with three of its top handful of prospects in the deal for Adrian Gonzalez in the previous offseason. This draft, in which the Sox had four of the first 40 selections, was an opportunity to replenish the farm system.
But in order for that to happen, the Sox would need to sign their picks. And doing so this year represented a challenge unlike any other that the team has experienced in recent memory.
Entering August 15, eight of the top 11 Sox draft picks remained unsigned. The team had committed to pursuing the best players on their board, rather than players who would sign eagerly.
The result was a wild confluence of negotiations that brought the Red Sox front office into a state of furious animation in the minutes leading up to midnight on the deadline day.
“A big blur.”
“Hell in a handbasket.”
Those were some of the descriptions of the final moments of the window to negotiate with draftees. In past years, the Sox had seen a couple of negotiations with picks go down to the waning moments of the deadline, including in 2010, when the team was trying to finalize deals with both sandwich pick Anthony Ranaudo and seventh-rounder Chris Hernandez in the final two minutes before the deadline.
But this year, nearly all of the team’s top picks remained in play. The status of first-rounders Matt Barnes and Blake Swihart, sandwich picks Henry Owens and Jackie Bradley, fifth rounder Mookie Betts and eighth-rounder Senquez Golson was unresolved until minutes before midnight, resulting in a string of negotiations that made the Boston front office sound like a trading room floor.
Based on conversations with a number of sources both inside and outside the Red Sox organization who were involved in the negotiations, here is a glimpse of how the shape of the Red Sox draft class was defined on the night of August 15.
There was a lengthy calm that lasted days before the craziness of the final minutes. As frustrating as it could be for the Red Sox to resign themselves to the reality that most of their deals would come down to the final day before the deadline, the team tried to use the period productively.
While several of the draftees were not yet ready to engage in negotiations on their signing bonuses, amateur scouting director Amiel Sawdaye worked with the advisors to the players to address some of the secondary details of deals. In some cases, the team was able to work out elements such as college scholarship packages for players as well as relevant incentive bonus plans. While not all of the draftees had those details addressed, those that did knock out those specifics could use the time on deadline day as an opportunity for a straightforward bonus negotiation.
The Sox also spent the days leading up to the deadline preparing themselves for each negotiation, thinking through the comparable players whom they would cite in negotiations, and then working to anticipate the potential comps that would be used by the advisors. Mindful that there could be a number of negotiations taking place simultaneously in the final minutes before the deadline, the team did what it could to organize for the chaos.
The team created a negotiating structure, assigning the advisors for different players to different front office members so that a number of deals could be worked out simultaneously. In the office, a support structure was also arranged.
Amateur scouting coordinator Jared Banner would serve as the point person who would send in all of the deals to Major League Baseball as they were negotiated. But in case anything happened to his computer or the Sox’ servers, contingency planning was necessary.
MLB had a hard deadline of 12:00:59 for signings. Word of any deal had to be received in New York by that time – not a second later. There was a chance that a player and team could agree to a deal, only to have a server hiccup – or one painstaking hourglass turning over and over on a screen – result in the deal being null.
The Sox had tried to prepare themselves for such an eventuality as best as they could. And so, in addition to Banner, the team also had other office staffers prepared to send in the terms either by other computers or Blackberries should any delay occur.
The Sox felt prepared for the negotiations, and they felt they had done what they could to address any IT issues that might crop up. The final days leading up to August 15, then, were spent trying (in some cases, unsuccessfully) to make limited headway in some of the negotiations, sometimes by bringing players to Fenway for physicals, and in some cases, by engaging the advisors.
In one case, the Sox discovered that they had a pleasantly unexpected and unusual scenario on their hands.
SENQUEZ GOLSON’S LONG DAY AT FENWAY PARK
Senquez Golson, an incredibly athletic outfielder who was raw but possessed above-average, across-the-board tools, had cracked open a door. A player who had seemed adamant for most of the summer that he would stay close to home to attend college while playing football and baseball at Ole Miss suddenly appeared to be wavering.
Golson was already enrolled at Ole Miss, and two days before the deadline, he participated in his first college football scrimmage. The defensive back picked off a pass in the game.
But while there was plenty of opportunity and satisfaction to be gained by playing two sports at Ole Miss, the reality of the Red Sox’ seven-figure offer started to become difficult to ignore. Indeed, Mississippi football coach Houston Nutt told Golson that he would advise his own son to take the guaranteed money.
While there was a twitter report two nights before the deadline that Golson had decided to sign with the Sox, such a scenario never occurred. However, Golson found the possibility of the $1 million signing bonus that the Sox had on the table appealing enough that, after much discussion with both the Sox, the Ole Miss program and his family, Golson decided to fly up to Boston on Monday to meet with the Sox, take a physical and decide his future.
He missed a plane flight on Monday morning, and certainly, Golson could have thrown up his arms at that point and said that he wasn’t leaving school. But he didn’t.
Instead, Golson, his mother and his girlfriend hopped on a flight through Dallas to Boston. When they landed in the early afternoon, the red carpet awaited.
Sox manager Terry Francona picked up Golson from the airport and drove him to Fenway. At the park, he got the recruiting pitch, with his name on the scoreboard as he got his first in-person glimpse at the field.
Golson met with numerous team officials, including GM Theo Epstein and scouting director Sawdaye. He received a phone call from Carl Crawford, a multi-sport star in high school, to discuss the merits of a baseball career.
Most 18-year-olds would have found it impossible to resist such a pitch. But even with the Sox offering to sweeten the $1 million bonus offer that was on the table when he flew up to Boston, Golson remained indecisive.
He spent the day in a conference room in the baseball operations office. Sox officials, especially Sawdaye, talked to him at length with their pitch.
It was a time-intensive undertaking given the difficulty that Golson was having with his decision. Yet for several hours after Golson set up residence in the conference room in the middle of the afternoon, there was little to be done in terms of negotiations with other players, and so the Sox were more than willing to try to address any concerns the outfielder might have about a pro ball career.
By about 5:30 or 6pm, however, the Sox had a good sense that Golson wasn’t going to sign. They hadn’t given up – indeed, Golson remained in their office past the midnight deadline, with the Sox circling back to him on numerous occasions in hopes that he might make the decision to sign.
Even so, the Sox recognized that with Golson potentially out of the equation, it would behoove them to lay the groundwork to use the money earmarked for him on another player.
THE LATER ROUNDS TAKE SHAPE: MOOKIE BETTS, NOE RAMIREZ AND CODY KUKUK
And so, the team rekindled talks with fifth-rounder Mookie Betts, a player who, like Golson, was an athletic, middle-of-the-field player with significant upside who had a scholarship offer to an SEC school (Tennessee).
Just days earlier, the team had reconciled itself to the idea that Betts might well not sign, as the team had not planned to meet his asking price. Moreover, Betts had declined to come to Boston for a physical, creating not only uncertainty but also the possibility that even if the Sox did strike a deal, it could be voided if some form of infirmity was discovered after the fact.
But with Golson potentially out of the mix, the Sox prepared to increase their offer to Betts. They laid the foundation for a negotiation later in the evening should Golson walk out of Fenway without a deal.
Around that time, the Sox’ first deal of the day became official, with MLB approving a deal with right-hander Noe Ramirez, a fourth-round pick, for $625,000. That deal hardly represented a breakthrough – the grounds for a deal had already become clear in the days leading up to the deadline – but the Sox still had one of their eight remaining players secured, and Ramirez’ was taken out of limbo.
“[The deadline day] was antsy for me,” Ramirez acknowledged after reporting to the Lowell Spinners.
But it likely need not have been, given that his deal represented little more than a formality.
As the day progressed, aside from the talks with Golson, there was only one other negotiation in which the Sox truly engaged. That was with left-hander Cody Kukuk, an athletic, 6-foot-4 left-hander with a fastball that touched as high as 94 or 95 mph and the athleticism to have received a scholarship offer at Kansas to play both as a position player and pitcher.
There was plenty to like about Kukuk, a seventh-round selection. His fastball velocity and ability to spin a breaking ball suggested a high ceiling, even if he represented a relatively raw talent who would need significant development time.
The Sox went back and forth with Rob Martin, the advisor to Kukuk, in the one negotiation of that day that was not conducted against a clock.
Kukuk had emailed all 30 clubs prior to the draft to say that he was only interested in signing for $1.05 million. The Sox had offered $500,000. The two parties met in the middle, with Kukuk receiving an $800,000 bonus around mid-evening.
And then… crickets.
THE BUILD-UP TO THE BIG FOUR
The Sox were engaged on Betts and Golson. But there had been little contact with the representatives of the four top picks: Barnes, Swihart, Owens and Bradley. Yet the Sox did not want to show their hand or betray any urgency that might reflect vulnerability in the negotiations.
On the one hand, the Sox felt strongly that patience is a critical part of negotiations. Bad deals are the byproduct of rushed deals that are borne of desperation. On the other hand, the team recognized that there was risk associated with a strategy that offered little room to blink.
“If this is a game of chicken that everyone really wants to win,” noted one participant to the negotiations, “everyone may lose.”
Aside from checking in on Golson, who by 10 or 10:30 had told Epstein, Sawdaye and the Sox that he was almost certainly planning to go back to school, the Sox used the hours as mid-evening transitioned to prepare for the brewing flurry of down-to-the-wire negotiations, reviewing the comps that would frame the discussions.
“We were preparing for the storm that we knew was around the corner,” said a team source.
Around 11:30, the Sox started to make some headway in negotiations. While Bradley was represented by Boras, who had in turn suggested that the outfielder would consider returning to South Carolina for his senior year, the threat was viewed as hollow given the absence of negotiating leverage that a senior possesses.
And so, it came as little surprise when representatives from Bradley’s side reached out to the Sox around 11:30pm. It was taken as evidence that a deal would get done, likely before the real chaos set in.
The development was in some respects expected. Bradley was viewed as a tremendous defensive center fielder with good bat speed and power potential, a player whom the Sox were thrilled to land with the No. 40 pick (perhaps two dozen spots after where he was expected to go at the start of the year). But Boras had several players who were bound to sign last-minute deals.
Boras had players such as No. 1 pick Gerrit Cole, No. 4 pick, Bubba Starling, No. 5 selection Anthony Rendon, former Sox draftee Alex Meyer, second-rounder Josh Bell and high school catcher Austin Hedges who would be in line for far greater paydays in a matter of minutes.
And given that the Sox had their own picks with undetermined fates, there was a mutual interest in concluding a deal for Bradley. Talks moved rapidly, to the point where Bradley suggested that his negotiation was done for $1.1 million by 11:47pm.
“That was the time where I got the call that we agreed,” said Bradley. "Just being able to meet inside the box to what I wanted the money to be, that was all there was to it.”
The prevailing atmosphere in the Sox front office during the Bradley negotiation remained calm, even as the deadline crept ever closer. There would be exchanges in the office, inquiries about whether the team had begun engaging yet with certain players and their advisors. For some, the answer was yes; for others, there was essentially no real dialogue on the deadline day until after 11:50pm.
But then, with just 10 minutes left to the deadline, the time for waiting had ended. The Sox needed to finalize Bradley while also sifting through negotiations with Barnes, Swihart, Owens and Betts, and also taking a final run at Golson.
“Between 11:50 and 12 it was straight chaos,” said one witness to the maelstrom. “Five people were on the phone at the same time with five different agents negotiating five different deals.”
Responsibilities were drawn. Sawdaye – who one year earlier had negotiated with advisor Greg Genske on the Hernandez deal – would once again handle talks with Genske, this time on Swihart, the switch-hitting catcher who was considered the toughest sign.
Epstein would sort out the last details of the Barnes negotiation. Special Assistant to the GM Dave Finley, after the Bradley deal was done, was assigned to negotiate the deal for 6-foot-6 lefty Henry Owens with his advisor, Joe Urbon of CAA. VP of Amateur Scouting and Player Development Mike Hazen was left to talk with Dan Lozano about the final details of a Betts deal.
That was the task in front of the Sox with 10 minutes remaining. A day in which time had been measured in drips suddenly transforming into a one where the seconds seemed to come as a flood. The Sox felt that their planning for those minutes had positioned them to handle them with an organized chaos, but it was chaos nonetheless.
Members of the front office would shout updates about the remaining time to the deadline, first in minutes, then in seconds. Meanwhile, as negotiations were moving, several people were yelling terms at Banner at once – a jumble of bonus figures and payment schedules that needed to be kept in order.
Betts got done around 11:54 or 11:55pm, agreeing to a $750,000 bonus that would be spread over five years. Under other circumstances, the Sox might have fought harder to trim perhaps a few thousand dollars or so from that final figure. But given the pressures of the deadline and the need to race through a number of deals, they were willing to move on once they reached a price point with which they felt comfortable.
Barnes was done soon thereafter. The Sox had been happy to grab the UConn right-hander when he remained on the board at the No. 19 overall pick, but the team had made clear from the outset that – as a college junior with little leverage – he was unlikely to see a bonus that was vastly in excess of the MLB slot recommendation of $1.386 million.
In the end, the Sox were entirely confident that he wouldn’t go back to school. They understood the pitcher’s desire to be treated fairly according to the standards of the deep pool of college pitchers taken in the first round, but they would not extend for him. They offered $1.5 million, and the pitcher (through advisor John Courtright, who was at Barnes’ house that night) accepted.
“I could have gone back to school. I could have played independent ball. I wanted to sign and start my professional career,” Barnes said. “11:59 was when my agent told me. It was exciting. He was there with [Barnes’ family], too, so we had talked throughout the entire day. It was exciting to finally become apart of the organization."
The team made a last run at Golson, who offered a final no – a disappointing outcome for the Sox, to be sure, but one that impressed the team’s decision makers. It is no small thing for an 18-year-old to not only turn down more than $1 million, particularly after receiving the red carpet treatment. Yet he still remained uncertain enough about his desire play pro baseball that he could say no to the Sox proposal, offering his answer directly to Epstein and Sawdaye.
And then there were two.
The Sox were in a position of strength in their negotiations with Barnes and Bradley, given where they went in the draft and the desire of both to turn pro rather than returning to school with little leverage.
But Blake Swihart possessed nearly as much leverage as anyone in the first round. He was the consensus top catcher in the draft, and a player who had been the top offensive performer on Team USA the previous summer. But given that his lifelong dream was to play at the University of Texas (Swihart’s wardrobe was dominated by Longhorns gear), his threat of going to school was credible – especially since, as a 19-year-old, he would be eligible to be drafted again after his sophomore year.
Owens, meanwhile, had made clear his interest in signing with the Sox. But the 6-foot-6 lefty had slipped in the draft largely as a result of signability concerns. He had been seeking a $2.5 million bonus to pass on a scholarship offer to Miami. As one of the most advanced high school lefties in the draft, he was in a strong negotiating position, a pitcher with the potential to be a first-round selection if he went to school.
Negotiations with both players started late and ran into the final minute, with the numbers shifting with startling rapidity.
Swihart had initially been seeking $6 million with about five minutes left to the deadline. A couple minutes later, that number dropped to $4 million while the Sox moved up to $1.75 million, the conversations getting more revved up as the deadline moved closer.
Finally, with about 20 seconds left, and a commotion in the Sox office as the remaining seconds were being shouted out, the sides met at $2.5 million – the third biggest bonus ever given to a Sox draftee under Epstein, but well short of the $4 million that many in the industry thought it would take to get Swihart done.
As for Owens, that, too, shifted several times in the last minutes, going from a $2.5 million bonus figure to $2.3 million to $1.9 million. In the last minute, Owens’ number was a $1.7 million with the Sox having come up to $1.5 million; the two sides reached their agreement in the final moments for a $1.55 million deal.
The final numbers were shouted out for the email to the Commissioner’s Office.
Of the eight players with whom the Sox had been negotiating, seven had reached agreements. Yet even then, with 12:01am having arrived, the anxiety could not yet end. The Sox waited anxiously to find out whether the deals had indeed arrived and met with MLB approval by the 12:00:59 deadline.
It took about 10 minutes for the dust to settle and for the Sox to get official word that, indeed, the servers had done their job, and all of the deals had gone through. It was a unique dynamic that required some time to digest, with members of the baseball operations department lingering in their subterranean lair for a couple hours before finally emerging into the early-morning air.
The Sox had committed more than $7.5 million to five players in a matter of minutes, acquiring a mix of high school and college talents whom they hope can impact the system for years to come. The team had shot high and landed almost all of its targets.
Yet as frenzied and compressed as the negotiations had been, the assessment of what the team accomplished will follow a very different schedule. It is one thing to draft players, another thing to sign them, and yet another thing to see what they will become.
Several years from now, the Sox may refer to the transformation of their organization achieve in the final minutes of August 15, 2011. Or they may bemoan the enormous expenditures that did not deliver the anticipated impact. Perhaps both.
Either way, the chaotic minutes that led to the players’ entries into the Sox system will now give way to a years-long examination of what they will be.