50 Most Notable Yankees Free Agent Signings: Colluding against Guidry and Randolph

This is no way to deal with franchise legends.

Say what you will about the Yankees’ organization, but once you’re considered part of the “True Yankee” family, they’ll generally always roll out the red carpet for you. Say what you will about his decision making and player evaluation capabilities, but George Steinbrenner was always willing to splash the cash to help the Yankees win, especially in the ill-fated 1980s.

Yet in the winter of 1986-87, George and the Yankees were willing to go along with a scheme to collude against some of the biggest name free agents, and that even included two of the best and most beloved Yankees of their era.

Willie Randolph
Signing Date: January 8, 1987
Contract: Two years, $1.75 million

Ron Guidry
Signing Date: May 1, 1987
Contract: Two years, $1.56 million

Fresh off leading the successful 1984 Olympics in Los Angeles, Peter Ueberroth officially took office as the commissioner of Major League Baseball in October of that same year. At an early meeting with the owners that elected them, Ueberroth reportedly said something that arguably helped kick off a couple years of collusion:

“Let’s say I sat each of you down in front of a red button and a black button…Push the red button, and you’d win the World Series but lose $10 million. Push the black button, and you would make $4 million and finish somewhere in the middle…the problem is, most of you would push the red one. You are so damned dumb.”

Behind closed doors, owners reportedly agreed to limit offers to position players to three years and pitchers to two. Teams would only be also allowed to sign opposing teams’ free agents if the previous team no longer wanted them. If that sounds ridiculous, it’s because it is. As baseball fans, I think most of us would roll our eyes at the purpose of the games and the league being anything other than wanting to win, but that became a opinion that several owners took to heart, and that still seems to be the case these days.

Over the next couple winters, the salaries of the contracts signed by free agents saw a fairly precipitous drop. In some cases, notable players didn’t even receive contract offers, while, in one famous case, Andre Dawson went to the Cubs and told them to name the price after he was failing to get much traction on the free agent market and outright refused to return to Montreal due to injury concerns with their turf.

The MLBPA quite obviously took notice of the massive drop in salaries and would file grievances against the owners on three separate occasions. By 1990, arbitrators had found in favor of the union on several different occasions. In the end, a settlement was reached where the owners ended up giving the MLBPA $280 million to distribute among members. As for Ueberroth, he lasted just one term as MLB commissioner and is one of few who haven’t been elected to the Hall of Fame, and helping facilitate collusion is almost certainly a large reason why.

However, before the collusion ended and things got back onto a more normal path, two Yankees greats ended up caught in the crossfire.

Following the 1986 season, both Ron Guidry and Willie Randolph were set to hit free agency. In addition to being two essential members of the late-1970s championship teams, the two had also been named co-captains ahead of the 1986 season. To say they were beloved Yankees is an understatement.

Guidry had spent his entire career to that point in the Yankees’ organization, having been a third-round draft pick of the team in 1971. He cemented himself in the Yankees’ rotation in 1977, helping them to the first of their back-to-back championships, but the next year was his true masterpiece. With 25 wins, a 1.74 ERA, and nine complete-game shutouts, Guidry put together one of the all-time best single seasons by a Yankees pitcher in 1978. He was unanimously voted AL Cy Young Award winner that season and finished second in MVP voting as well.

He never quite reached those lofty heights again, but Guidry remained an excellent pitcher for the Yankees for most of the next decade. Just two seasons before hitting free agency, he led the league in wins for the first time since his ‘78 epic, winning 22 in 1985. His win-loss record the next year wasn’t particularly shiny, but his rate stats showed that he was still an above average pitcher.

Having been drafted and developed by the Pirates, Randolph played one season for them in 1975, but was soon dealt to New York as part of a deal that sent Dock Ellis, of LSD no-hitter fame, from Pittsburgh to New York for Doc Medich. Randolph hit the ground running in the Bronx, making an All-Star Game in his first real big league season.

Over the next decade plus, he became a steady, dependable presence both in the Yankees’ lineup and on the field at second base. As he accumulated a close to Hall of Fame level 62.1 fWAR, Randolph made five All-Star teams, won a silver slugger, and received down-ballot MVP votes on a couple of occasions, in addition to also being part of the World Series winning teams of ‘77 and ‘78.

The Yankees were a perfectly solid team in 1986, finishing second in the AL East, 5.5 games back of an eventual pennant-winning Red Sox team. Randolph and Guidry were among the best contributors to that team, you would’ve expected the Yankees to be eager to bring them back, never mind their status as team captains. Nonetheless, they ended up among those caught in the owners’ collusion. For as much is made about George Steinbrenner’s relentless determination to win at all costs, it shouldn’t be forgotten that he was willing to along with the other 25 teams in illegally stifling salaries.

After Randolph and Guidry declined arbitration terms in December, the Yankees just… didn’t negotiate with their leaders. It was now a pattern after New York also colluded against popular veterans Tommy John and Phil Niekro the previous offseason, as well. The nature of collusion meant that other teams weren’t particularly making an effort either. Guidry, for example, held talks with the Dodgers, Orioles, and Twins, but those didn’t amount to much. The teams’ “strategy” in holding talks was also that there was a January 8th deadline in which if teams did not re-sign players, they then couldn’t until May 1st.

In the end, Randolph eventually signed before the deadline. On January 8th, he agreed to a two-year deal for $1.75 million. A furious Guidry did not budge, however. The two sides were just $50,000 apart on their negotiations, but couldn’t finalize the deal by the deadline. Afterwards, Guidry was quoted as saying:

”I’m disappointed, but it just didn’t work out. I was the one kneeling down and yet they didn’t want to try. I came down $700,000 in seven hours and it took them two months to come up $25,000. It was a matter of principle then.”

The way the news was reported at the time, it seemed as if the long relationship with the Yankees and Guidry was over, as surely he wouldn’t wait until May. He was one of eight players who hadn’t re-signed with their teams by the deadline (peak Tim Raines the most famous of the group), which hadn’t yet happened in the previous collusion years. However, again, the teams were colluding, and only the Orioles made even a half-hearted attempt at Guidry, and that still didn’t go anywhere. In the end, May came and Guidry eventually agreed on a two-year, $1.56 million deal with the Yankees.

While in the moment, the teams might’ve felt like they’d won in these negotiations, the MLBPA would win their grievances against the owners. Even before the aforementioned $280 million settlement, Randolph and Guidry both received money from a $38 million judgement several players won in October 1989 (by which time Guidry had retired and Randolph had moved on to the Dodgers). Especially in Guidry’s case with the teams just $50,000 apart, Steinbrenner and the Yankees ended up having to give him more than that in the settlements.

In the end, the Yankees got both of those beloved legends back in the fold. Both went on to be coaches for the team after their playing careers, and both still make appearances at Yankee Stadium today, with this period in history all water under the bridge — particularly since they’re most often asked about those ‘70s champions rather than the turbulent ’80s years. However, you could also easily imagine someone wanting to throw up a finger at being treated like that.

Anyway, as a pro-labor lefty, suck my ass, Peter Ueberroth.


See more of the “50 Most Notable Yankees Free Agent Signings in 50 Years” series here.

Category: General Sports