What are the Boston Red Sox Thinking with Ryan Dempster?

Jayne Kamin-Oncea-USA TODAY Sports

He does an absolutely horrible Harry Carey impersonation, but certainly comes across as one of baseball’s most likable guys. This Canadian is one of baseball’s hardest workers and certainly gives you a solid effort day-in and day-out. But considering his age (35) and the Tommy John Surgery he had back in 2003, was a two-year $26.5 deal really in the best interest of the Boston Red Sox?

Let’s rewind a bit to last season. Dempster was having one of his best seasons as a professional for the Chicago Cubs. Since the Cubs were such a terrible team, they decided it would be in their best interest to trade Dempster. They had a trade worked out with the Atlanta Braves, but Dempster invoked his no-trade status and killed the deal. He eventually wound up on the Texas Rangers, but there was bad blood on both sides. Rumors in the Chicagoland area started to surface that Dempster was having some off-the-field issues with his family and that caused his indecisiveness on the original trade. After he went to the Rangers, he wound up 7-3 but with an ERA of 5.03.

So it makes me wonder why the Red Sox would give Dempster a two-year deal? I cannot imagine teams were lining up longer-term deals for him, so why would the Red Sox give him that extra year of pay? There’s been a lot of wear and tear on his arm, and at his age, he isn’t getting any better. Unless the Red Sox thing much higher of Dempster than I do, but even so, this just doesn’t make a whole lot of sense in the whole grand scheme of things.

Last season, after it became obvious the Red Sox weren’t going to make the playoffs, they decided to unload several high-priced players and long-term contracts. It was a good move at the time, but with where this team currently is, this move totally defies logic.

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