As the MLB non waiver trade deadline slowly approaches, the Toronto Blue Jays fans wonder quietly and very loudly through twitter and other means of communications on whether or not GM Alex Anthopoulos will make a trade to upgrade their pitching. While we wait and see if anything will be done, let us look at some of the memorable trades Anthopoulos has made since he was made GM in 2009.

Blue Jays Can’t Repeat Past Trade Mistakes

In early 2011, former Blue Jays all-star Vernon Wells contract became an obvious problem ($126 Million over 7 seasons) Anthopoulos managed to send him to the LA Angels of Anaheim in return for Mike Napoli and outfielder Juan Rivera. This was a great move for the books, however the trade expanded into something much worse. Anthopoulos flipped Mike Napoli to the Texas Rangers for Frank Fransisco who was not much help for the Blue Jays. While Napoli would go on to hit 30 homeruns with a .320 average that season and then of course later on he would go to Boston and help them win a World Series.

Last November Anthopoulos may have made the best trade of his career when he acquired Josh Donaldson from the Oakland A’s for Brett Lawrie, Sean Nolin, Kendall Graveman and Franklin Barreto. Donaldson was voted into this year’s All-Star game with the most votes ever received, he has also been the teams MVP from day one and could be a potential MVP candidate when the season is done. Hopefully the Jays can lock him up for a long time, because he has now become a key part in the Jays’ core moving forward. We need to see how Donaldson preforms for the rest of his tenure in Toronto, but right now this is one of the best trades.

A trade Anthopolous made in 2009 however is arguably his worst. In December of that year, Anthopoulos made one of his first big trades and that was moving beloved all-star, Cy Young winning, ace Roy Halladay to the Philadelphia Phillies for Travis d’Arnaud, Kyle Drabek and Michael Taylor. This trade looks and frankly is terrible, none of these guys turned out to help the Jays on the field and Toronto didn’t even get a player who was ready to play right away. Drabek was the only player left in the system, but didn’t pan out due to injuries

Travis d’Arnaud would be sent to the New York Mets with Noah Syndergaard, John Buck and Wuilmer Becerra for RA Dickey, Mike Nickeas and Josh Thole. This could become another terrible Anthopoulos trade, if the Jays don’t make the playoffs this season and make some noise, but for the time being it’s falling under the not so great trade category. As for Michael Taylor was traded in a move that eventually brought in Devon Travis. We don’t know how Travis will turn out in the long run, but if his career is the way this season has gone, then he will be a steal. If you look at it this way Halladay was traded for RA Dickey, Josh Thole and Devon Travis.

Finally we shall end on a good, kind of weird note. July 31st 2009 the Blue Jays traded away Scott Rolen for Josh Roenicke, Zach Stewart and Edwin Encarnacion. This is a good trade, because they got a solid slugger in Encarnacion, the weird part is he was selected off the waivers by the Oakland Athletics November of 2010, but was granted free agency and then signed with the Blue Jays long term.

These are the most notable trades that Anthopoulos has made. Going through his list of trades you can see that he is trying to make a splash, but has had a bad knack of falling short. The Jays need a pitcher or two but let’s hope he hits a home run and not another disastrous bust, because let’s face it they can’t afford it this year.