Young Cashman mapped out Yanks' dynasty

May 18th, 2020

Executive Access is running a series of throwback episodes from 2017, including this week’s episode featuring Yankees senior VP/general manager Brian Cashman.

When Brian Cashman assumed the general manager’s chair shortly before Spring Training in 1998, he inherited a team that had the look of a serious contender.

After all, the Yankees had won the 1996 World Series and returned to the postseason in '97, so he wasn’t exactly starting from scratch.

New York had already made some additions that winter, signing free-agent veterans and . The Yankees also dealt Kenny Rogers to the Athletics for underachieving third baseman , a deal Cashman -- still the assistant GM to Bob Watson -- put together with Oakland GM Billy Beane.

“Bob gave me a lot of autonomy, so as Bob’s assistant, I took all of the young general managers,” Cashman said in a 2017 sit down with the Executive Access podcast. “He was working with the John Harts, the Pat Gillicks, the John Schuerholzes, the Ron Schuelers, the Syd Thrifts; I was given Kevin Towers, Billy Beane, all the younger, newer guys in the game.”

Watson had the final call on the Nov. 7 deal, but less than two months later, those calls belonged to Cashman after Watson stepped down as the club’s GM. Cashman, just 30 years old at the time, was tabbed as his replacement. Watson passed away Thursday at age 74 after a long illness.

Three days after being named GM, Cashman made his first big move, completing a long-anticipated deal with the Twins that brought All-Star second baseman to New York for four prospects and $3 million cash.

Seven weeks later, the Yankees made another big move, signing Cuban defector to a four-year, $6.6 million contract. Cashman said the moves weren’t made in an effort to put his own stamp on the team, but simply as a way to get the Yankees back to the World Series after their disappointing American League Division Series loss to the Indians the previous October.

“Any deal that I’ve made since I’ve been here is not about putting any imprint in any way, shape or form; it’s just about, 'Is this going to make us better?'” Cashman said. “In the short or long term, is this going to have some sort of benefit? Or you don’t do the deal. Whether it’s clearing money, whether it’s improving a position, and in most cases -- especially back then -- it was short-term decision-making. It was about, 'How are we going to put ourselves in the position to be a world champion over the next six months, forgetting the second or third or fourth year out?' All those decisions played out with that type of decision-making in play.”

The 1998 Yankees, who are part of the 64-team field in the MLB Dream Bracket 2: Dream Seasons, opened the season with a 1-4 record, sparking plenty of speculation that Cashman and manager Joe Torre could be in George Steinbrenner’s crosshairs before too long.

“I already knew what I was getting into,” said Cashman, who had been part of the organization for more than a decade. “I grew up here in this Yankee system. I think if you were trained outside the Steinbrenner family and imported in, you were already preconditioned to other stimuli, so to speak, or a certain way about how things operated. I think it would be very hard to adjust to working under the Boss if you had success somewhere else, came here and assumed you could go about your business the same way here.

“I grew up under the Boss’ rule; he was extremely difficult to work for, extremely demanding, and every day potentially the game plan would change. You really just had to adjust and work well with all your co-workers to help support each other to whatever end he wanted on any given day. It was just a different culture compared to the normal environments in other baseball operations throughout the game. I just think I was more prepared because I grew up under him. … That allowed me to have perspective and staying power and roll with everything because nothing was new to me.”

The Yankees went on to win their next eight games, and 22 of the next 24 to seize control of the AL East. They never looked back, winning 114 games in the regular season and 11 more in October, capturing their second World Series title in three years.

Cashman’s first year as the GM had been, in his words, a “magical carpet ride.” Their 125-50 record thrust them into the conversation for greatest team ever, but as the GM assessed his club that winter, he thought back to the 1996-97 offseason.

“After we won in ’96, we brought almost the same team back except for John Wetteland; he left as a free agent, so became the closer,” Cashman said. “We mustered a Wild Card and first-round knockout in ’97 with essentially the same team. That team did not gel like it did the previous year; we had infighting. It was like the Three Musketeers in ’96 -- all for one and one for all -- and in ’97, it was completely different even though it was almost entirely the same personnel. I learned from that.”

had been a key cog in the 1998 machine, going 18-4 while throwing 214 1/3 innings -- and one perfect game. Wells was wildly popular in New York, but Cashman noticed that the pitcher was really soaking in the success, partying hard and putting on weight that winter.

“There was just a little different vibe of, 'Will we be as committed going into next year in ’99 as we were in ’98?'” Cashman said.

Enter , the back-to-back defending AL Cy Young Award winner, who was potentially available via trade. As good as the 1998 team had been, Cashman was intrigued.

“You have to always be open-minded to remake yourself and somehow improve,” Cashman said. “The only thing [Clemens] hadn’t won is a championship. I knew that man was going to be motivated and all in.”

On Feb. 18, 1999, Cashman and the Yankees sent Wells, Homer Bush and Graeme Lloyd to the Blue Jays in exchange for Clemens, the five-time AL Cy Young Award winner.

New York went on to win the World Series in 1999 and 2000, becoming the third Yankees team -- and fourth overall in MLB history -- to win three straight championships.

“We had a lot of discussions internally, and if we could find the right deal, we felt that going forward, Roger would be a huge impact on us,” Cashman said. “We made the tough decisions; that was not an easy one, but we felt it was better as we moved forward, that would allow us to get closer to another championship or championships -- and it played out that way, to be quite honest. It was a tough call, but I think it was the right call.”

Listen to Cashman’s entire interview on Executive Access, available on Apple Podcasts, Spotify, Google Play, Art 19 or wherever you get your podcasts.