It's the type of question that could be a sensitive topic to some, but Blue Jays president Mark Shapiro didn't see it that way. He was open and honest in his assessment of a trade that happened all the way back in 2001 during his first full year as Cleveland's general manager.
"I would like to think -- more importantly 'we' because no trade is made by one person -- have learned from each of our ill-fated trades," Shapiro said. "While there have been those that may be perceived as worse due to outcomes, I feel the trade of Robbie Alomar to the Mets in my first offseason as GM was our most valuable lesson.
"We traded Roberto for Matt Lawton, Alex Escobar, Billy Traber and Jerrod Riggan. That was a trade that was firmly in the middle. We were recognizing that we needed to rebuild with the addition of prospects [in Escobar, Traber and Riggan] but also looking to remain competitive [with Lawton].
"Had we been more firmly committed in one direction -- either contending or rebuilding -- we would have made a trade that netted a better return. We learned from that experience and adjusted to make better trades with Bartolo Colon and those that followed him, providing us a core of talent that formed the teams of 2005-07."
Lawton was a proven Major Leaguer at the time of the deal, and he went on to spend three years in Cleveland, including a 2004 All-Star campaign. He made the Indians better in the short term, but the Tribe finished under .500 during each of those years. By the time Cleveland was ready to contend in 2005, Lawton was sent to Pittsburgh for left-hander Arthur Rhodes.
Shapiro was named the Sporting News' Executive of the Year twice (2005 and '07), and the Indians captured the American League Central crown in '07 before eventually falling to the Red Sox in the AL Championship Series. It was a very successful time in franchise history, but it sounds like Shapiro, with hindsight on his side, thought it could have been even a bit better.
These are important lessons moving forward, because the Blue Jays could find themselves in a similar situation a year from now. Jose Bautista, Edwin Encarnacion, R.A. Dickey, Drew Storen and Brett Cecil are eligible for free agency at the end of the season, and Toronto will have to decide whether it can remain competitive or instead have to rebuild.
With a team expected to contend in 2016, these type of decisions don't need to be made now. The current focus is winning this season, but after that, Shapiro and his front-office team will have to make some tough choices. No matter what they ultimately decide, expect the organization to move in one clear direction, because it's Groundhog Day and Shapiro won't want to repeat those past mistakes.