The Yankees’ Josh Donaldson Trade Is Already Drawing Comparisons to Roger Clemens’ 1999 Arrival

Article Highlights:

  • New York Yankees general manager Brian Cashman compared the team’s recent Josh Donaldson acquisition to acquiring Roger Clemens in 1999
  • Both moves involved players who had pre-existing negative histories with the Bronx Bombers
  • The comparison is an intriguing one, although there are significant differences between Clemens and Donaldson’s pre-existing Yankees beefs

It almost sounds like the punchline to a terrible joke. What do New York Yankees third baseman Josh Donaldson and seven-time Cy Young Award winner Roger Clemens have in common?

No, the answer isn’t that both are former American League MVP Award winners.

At first glance, there doesn’t seem like there’d be too many parallels between a 35-year-old third baseman and one of the greatest pitchers in league history. However, Yankees general manager Brian Cashman, the man responsible for bringing both to the Bronx, would clearly disagree with such an assessment.

Yankees general manager Brian Cashman compared the Josh Donaldson trade to Roger Clemens’ 1999 arrival

New York Yankees third baseman Josh Donaldson (L) in 2022 and pitcher Roger Clemens in 1999.
New York Yankees general manager Brian Cashman sees a significant comparison between Josh Donaldson (L) and Roger Clemens | Cliff Welch/Icon Sportswire via Getty Images; Tony Ranze/AFP via Getty Images

Days after the 99-day MLB lockout ended, Cashman stunned the baseball world by trading former All-Star catcher Gary Sanchez and fan-favorite infielder Gio Urshela to the Minnesota Twins for a package involving Donaldson, a three-time All-Star with 251 career home runs to his name.

What made the transactions so shocking is Donaldson’s pre-existing history with the Yankees, specifically ace pitcher Gerrit Cole. The veteran third baseman made waves last season when he suggested the four-time All-Star’s spin rates dropped after the league barred pitchers from using sticky substances.

When Cole faced Donaldson days later, the veteran right-hander struck out nine, including Donaldson twice, in a victory and stared the third baseman down in the first inning.

Yankees fans too young to remember the dynasty years might not know Clemens, who spent two stints with the franchise, had his own issues with the Bronx Bombers. While pitching for the Toronto Blue Jays, he plunked Yankees third baseman Scott Brosius in the back in September 1998 and blamed the issue on a bruised right palm. That didn’t stop Yankees pitcher Hideki Irabu, who hit Blue Jays outfielder Shannon Stewart in the elbow an inning later.

The benches cleared at Yankee Stadium, and then-Yankees outfielder Darryl Strawberry earned a three-game suspension for throwing a punch.

What does all of this have to do with Donaldson? Nearly 25 years after Cashman gave up significant assets to acquire Clemens, he did the same for Donaldson — and Cashman, the Yankees’ general manager since 1998, is staying optimistic that history will repeat in more ways than one.

“When the dust settled, [Clemens] became one of the more impact Yankees I’ve ever had,” Cashman said, according to’s Bryan Hoch.

The comparison is an intriguing one, although there are significant differences between Clemens and Donaldson’s pre-existing Yankees beefs

Cashman’s comparison is certainly intriguing, and it definitely makes sense. It’s also worth noting the Yankees’ longtime GM has never shied away from bringing in ex-rivals, including former Boston Red Sox center fielder Johnny Damon, if it meant helping the team win the World Series.

We’ll let the one championship in 20 years speak for itself on that one.

However, there are two noteworthy differences between Clemens and Donaldson, and one is simple. Donaldson’s issue with the Yankees only involved one player, albeit one who is the team’s highest-paid player and reportedly extremely sensitive. The Clemens incident spurred a brawl in a time when players actually threw punches.

The other difference involves the rosters at the time. Those 1999 Yankees were coming off a 125-win campaign the year before and a second World Series title in three years. However, these Yankees, despite regularly boasting one of the league’s highest payrolls throughout the 21st century, have made a single Fall Classic appearance since the start of the 2004 season.

Clemens arrived to improve an already elite team, one primarily consisting of battle-tested veterans and homegrown prospects, and the Yankees won each of the next two World Series. Donaldson is the latest veteran addition trying to help a team with highly-paid players who might not be perfect fits (see Cole, Gerrit) finally break through and win a pennant for the first time since 2009.

The 2022 Yankees are a team that might quickly need Donaldson to fill a lacking void in the locker room. Conversely, those 1999 Yankees already had that core, and that’s a significant reason why the Clemens trade worked.

Cole and Donaldson at least appear ready to move forward and leave the 2021 kerfuffle in the past

To Cole and Donaldson’s credit, both said the right things following the trade. On Monday, March 14, Hoch reported that both players met in manager Aaron Boone’s office and shook hands upon the third baseman’s arrival in Tampa, Florida.

Cole, who is expected to be the Yankees’ Opening Day starter for the third straight season, said Cashman called him the night before to inform him about the trade.

“It’s actually not all that uncommon for [Cashman] to fill me in on stuff before it hits the wire,” Cole told reporters. “There’s probably a little extra reason why he reached out specifically last night. But look, if you’re committed to winning a championship, this stuff doesn’t matter.”

Donaldson said he believed both players “felt very good” about where things ended after their meeting.

“At the end of the day, we’re here to play baseball,” Donaldson said. “I think those guys in that clubhouse know from watching me, as a competitor, that I want to win baseball games. I think that they respect that.”

If Cole and Donaldson lead the Yankees to a 28th World Series title this fall, something tells us the fans will be more than happy to forget about last year’s kerfuffle.

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