Yankees Christmas Shopping Through the Years

By Mike Whiteman

December 24, 2023

The holiday season is here! For many, this is a time to slow down a bit, take some time off, and connect with family and friends. That's not necessarily the case in the Major League Baseball offseason. The news that Yoshinobu Yamamoto has spurned the Yankees for the Dodgers was not the holiday cheer that fans were waiting for. It has created the need for Brian Cashman to pivot quickly and improve the team in other ways. So, he'll likely be working over the holidays. He won't be the first Yankee GM to do so. Here are some notable acquisitions the team has made this time of the year . December 19, 2002 - Godzilla comes to New York! The Yankees announced that Hideki Matsui, one of the greatest sluggers in Japanese baseball history, has agreed to a contract. It was a great signing for the Yanks, as Matsui slashed .292/.370/.482 in Pinstripes, and was even better in the postseason - .312/.391/.541, including the 2009 World Series MVP.

December 21, 1995 – David Cone had been acquired during the stretch run of 1995, and his 9-2, 3.82 mark helped propel the Yankees to the American League Wild-Card. On this day, the Yanks and Cone came to an agreement on a three-year contract.

Cone became a beloved Yankee, going 51-24 over the next four seasons, helping lead the team to three World Series titles and hurling a perfect game in 1999.  

December 27, 1984 – Well, not all gifts are winners. The Yanks signed free-agent pitcher Ed Whitson to a huge (for the time) contract worth $4.4 million over five years. The signing was a mystifying one then and now, as he came to the Bronx with a career losing record and 3.60 ERA. Sadly, Whitson was not a good fit, with a brutal 5.38 ERA in a season-plus with the Yankees and an infamous fight with manager Billy Martin.

December 28, 1995 – Future Hall-of-Famer Tim Raines joined the Yankees in a trade with the Chicago White Sox. Raines was a shadow of the great player he had been for the Montreal Expos, but was a useful role player and a positive veteran influence in the late 1990s Yankee teams.

December 28, 2015 – In one of the more controversial deals made in recent team history, the Yanks picked up lefty reliever Aroldis Chapman, at what many called a discount price, in a swap with the Cincinnati Reds. Chapman had been under MLB investigation for domestic violence at the time of the trade, and was eventually suspended for 30 games in 2016. He was later dealt to the Cubs at the 2016 trade deadline, then signed by the Yanks as a free agent after the season was over. Chapman's Yankee stats look pretty good (153 saves, 2.94 ERA), but postseason failings and his ugly exit hang a cloud over his time with the team. December 30, 1995 - Another signing that didn't work out as hoped - the Yankees signed Kenny Rogers to a free agent contract. The lefty was at least serviceable in 1996 (12-8, 4.68, 107 ERA+) as the Yanks returned to glory with their World Series win. A 5.65 ERA in 1997 landed Rogers on the trading block, and he was dealt to Oakland for future World Series MVP Scott Brosius. December 31, 1974 - The first big free agent, Jim "Catfish" Hunter, inks a huge (for its time) five year - $3.75 million contract with the Yanks. Hunter was Cy Young Award caliber in 1975 (23-14, 2.58) and good, thought not great, afterwards. Many say the Hunter signing set the tone for the transformation of a franchise that hadn't won anything since 1964 to the team that won three consecutive AL flags and two World Series championships.

January 1, 2005 - Hero of the 1996-2001 Yankees Tino Martinez returns to the Yanks. Martinez had left the team after the 2001 season as they pursued free agent Jason Giambi. Tino and Giambi split time at first base in 2005, with Martinez a frequent late-inning defensive replacement. The Yankees declined to retain Tino after the season was over, and he subsequently retired. Happy Holiday to all readers! Thank you for reading and commenting on my articles in 2023, and I'm looking forward to more great Yankees talk in 2024!