I decided to put together a list of the most memorable moves of the last 25 years. By "most memorable", I don't mean "best". Sometimes a move seems great at the time it's made and then turns out to be a bad one or an insignificant one. I'm judging this by the my own memory of which moves excited or intrigued me most as they were made. I chose one move (or two related moves) each year. The list is below. Keep in mind that 1989 (for example) indicates the move was made in between the last game of 1989 and the the first game of 1990.
1989 - After a horrible 103-loss season, the Tigers acquired free agents Tony Phillips and Lloyd Moseby at the December Winter Meetings. It was a different world back then. I was at graduate school at UConn and had no television or computer. Even though the moves were officially made two days apart, I learned about both of them on the same day in the newspaper.
1990 - Rob Deer was signed as a free agent the day after Thanksgiving when usually nothing is happening. I knew his limitations, but he was an intriguing player and the timing of the deal made it memorable. They later traded pitcher Jeff Robinson for Mickey Tettleton. I should have liked that move more, but it just didn't have a big impact at the time. It was another one that I learned about in the paper a couple of days after it happened.
1991 - This was a quiet off-season, but I'll go with the signing of outfielder Dan Gladden. He was a bad player, but I remembered his grit in the Twins 1987 and 1991 championship seasons and I somehow believed that would help the Tigers.
1992 - One of my favorite players - Kirk Gibson - returned the Tigers and he of course would make them a winning organization again.
1993 - The Tigers signed pitcher Tim Belcher. He was coming off a poor season, but he had quite a bit of past success and I was surprised the Tigers were able to sign him. He and another free agent acquisition David Wells were surely going to give the Tigers the winning pitching staff they lacked the last few years.
1994 - Wow, I've got nothing. How about selecting outfielder Todd Steverson in the Rule 5 draftt?
1995 - The move of the off-season didn't happen until spring training. Pitchers Cade Gasper and Sean Bergman were traded along with Steverson to the Padres for catcher Raul Casanova, pitcher Richie Lewis and outfielder Melvin Nieves. There was Todd Steverson creating more off-season excitement. Plus, I knew that Casanova and Nieves would be two important building blocks of a future champion.
1996 - One of the many Brad Ausmus deals was made during the winter meetings. Ausmus went to the Astros along with Jose Lima, Trever Miller, C.J. Nitkowski and Daryle Ward. In return, the Tigers received Doug Brocail, Brian Hunter, Todd Jones and Orlando Miller. Boy, what a wheeler and dealer Randy Smith was. The Tigers were finally in good hands.
1997 - On expansion draft day, the Tigers moved Travis Fryman to Arizona for Matt Drews, Gabe Alvarez and Joe Randa. I didn't care for that move, but it was memorable because of Fryman and the uniqueness of the expansion draft.
1998 - The Tigers signed Dean Palmer. I knew he wasn't that great and that the Tigers overpaid, but it was unusual for the Tigers to make such a high profile signing. The later signing of Gregg Jefferies and trade of Luis Gonzales on the same day made me seriously question Smith's competency as a GM.
1999 - This was a big one and it came very early in the Hot Stove season. Juan Gonzalez, Danny Patterson and Gregg Zaun came from the Rangers in exchange for Alan Webb, Fran Catalanotto, Francisco Cordero, Bill Haselman, Gabe Kapler and Justin Thompson. All of that for ONE year of Juan Gonzalez? There was no longer any questions about the competency of Randy Smith.
2000 - Another big Brad Ausmus deal by Smith - Ausmus, Brocail, Nelson Cruz (no, not that Nelson Cruz) went to the Astros in exchange for Roger Cedeno, Chris Holt and Mitch Meluskey. I actually liked that deal because Meluskey was going to be a stud.
2001 - Juan Encarnacion and Luis Pineda were traded for Dmitri Young.
2002 - Pitchers Mark Redman and Jerrod Fuell were traded to the Marlins for pitchers Rob Henkel, Gary Knotts and Nate Robertson. Firmly in the internet era now, we knew ahead of time that Redman had been traded and I wasted a lot of time trying to figure out who they would get back.
2003 - That was a fun off-season after a miserable regular season. First they signed second baseman Fernando Vina and Rondell White as free agents, moves that inspired a press conference at the time. Yeah, that was a different time. Then they stole Carlos Guillen from the Mariners. The most ,memorable move came in January though - the signing of Pudge Rodriguez. The Tigers were a real organization again.
2004 - Another big free agent signing in Magglio Ordonez. Not quite as shocking as the Pudge signing, but still a big deal.
2005 - Signed Kenny Rogers. Big free agent signings were becoming less exciting now.
2006 - Gary Sheffield from the Yankees for pitchers Anthony Claggett, Humberto Sanchez and Kevin Whelan. I was a Sheffield fan and liked this deal.
2007 - The most memorable Tigers move of my lifetime - MIGUEL CABRERA. THE MIGUEL CABRERA came to the Tigers in an eight man-player with the Marlins. I couldn't believe they were able to trade only prospects for the best young hitter in the game.
2008 - Finally a quiet off-season. The biggest move was Matt Joyce for Edwin Jackson. The most memorable thing about it was getting my unexciting blog posting linked by Rob Neyer. He was apparently looking for a Tigers blogger who didn't like the trade and I fit that description.
2009 - The Tigers lost Curtis Granderson and Edwin Jackson and acquired Phil Coke, Austin Jackson, Max Scherzer and Daniel Schlereth. I hated this deal at the time.
2010 - Victor Martinez was signed. Some felt the Tigers overpaid, but I liked this signing.
2011 - Prince Fielder was signed. It was hard to dislike what basically seemed like a gift from owner Mike Ilitch, but it didn't seem like a great fit and it appeared that the money could have been better spent..
2012 - The signing of Torii Hunter was the biggest move of a relatively tame off-season.
2013 - Fielder was traded for Ian Kinsler in what was seemed like a genius move by GM David Dombrowski
2014 - Is the Anthony Gose deal going to be their most memorable moment this off-season? They also re-signed Martinez but that too predictable to be memorable.