Thinking about it a little more:
The Orioles were not good when they traded for Glenn Davis. They were coming off a 76 win 1990 season but there was some reason for optimism. 1989 had been great and with Ben McDonald and Mussina in the wings, there was some young talent to look forward to. If they don't trade for Davis and keep Schilling, Finley and Harnisch, they might not be as bad in 1991. And in 1992, they could have won more than the 89 games that they won. The whole 1990s probably looks a lot different for this franchise, including the playoff years of 1996 and 1997.
I'm 50/50 on this one, honestly. I can see it both ways.
There's nothing stopping a team from not offering guaranteed contracts, other than the fact that the only players you would get are the guys no other team will offer a contract to. Guaranteed contracts are a drop in the bucket to the Yankees, Red Sox, and Dodgers. They can afford the inevitable losses on some of those deals. Teams like the Orioles and Rays can't afford those huge losses and have to be much more careful. There's no way that the Yankees and the other rich teams will ever give up that competitive advantage and stop offering guaranteed contracts..
Thinking about this in @Sports Guy's choose one thread:
There are two absolutely atrocious franchise altering deals that this franchise has made. I'm probably missing another obvious one like the Eddie Murray deal. While that deal was bad, I don't think it comes close to the Chris Davis contract and the Glenn Davis trade.
The Orioles traded Curt Schilling, Pete Harnisch and Steve Finley to the Astros for Glenn Davis before the 1991 season. Davis was a tremendous flop, could never stay healthy while Curt Schilling went on to a borderline HoF career, Steve Finley hit 300 homers and stole 300 bases, won Gold Gloves and Harnisch ended up being a very solid pitcher.
I don't think anyone could have predicted back then that those three would go on to reach the heights that they did. Now I was 9 when the Orioles traded for Glenn Davis, I remember being excited about it. I'm not sure what older and more sophisticated fans were thinking.
I don't need to re-hash what a disaster the Chris Davis contract has been. The issue here for me is that we can see what Schilling, Finley and Harnisch did over their careers and while they might not have been able to replicate those careers in Baltimore, it's easier to think that they could have done so.
With the Davis contract, the "what if's" become a lot more murkier. If we let Davis walk, do we re-sign Machado? What else could that money have been spent on? What would the roster look like today? It's a lot harder to say.
So Glenn Davis vs. Chris Davis. Which was the worst in the history of this franchise?