Rolling the dice on prospects

It's that time of year.

No not summer vacation or back to school season.

I'm talking about the annual make or break month where Major League Baseball teams decide if they're buying or selling by the July 31st non-waiver deadline.

By selling, you're especially folding on the season and turning your attention to the future; usually by unloading free agents to be, or contracts that burden your team's ability to compete financially in the future.

The Chicago Cubs and their South Side rivals, the White Sox, kicked off "Christmas in July" a week and a half ago when pitcher Jose Quintana was dealt North for a range of prospects including Eloy Jimenez, Dylan Cease and Matt Rose.

Over the next week, teams will have to decide if this is their year or not.

In the American League, six teams sit within five games of the second wild card spot currently held by the Tampa Bay Rays.

Over on the Senior Circuit, no team is within five games of the Colorado Rockies for the second wild card, with the closest being the aforementioned Chicago Cubs.

It's clear the Cubs are taking a shot at the second wild card, or more likely, the division leading Milwaukee Brewers who they trail by only a game entering play Sunday.

Herein lies the struggle facing both buyers and sellers at the deadline.

Are you willing to roll the dice on:

1.) Making the playoffs.
2.) Ensuring that you don't give too much up (in the case of buyers) or get nothing of value in return (in the case of sellers).
3.) The player(s) you trade away coming back to bite you.

Eight years ago this December, the Toronto Blue Jays dealt fan favorite, and arguably greatest player in franchise history, Roy Halladay, to the Philadelphia Phillies for pitcher Kyle Drabek, catcher Travis d'Arnaud and outfielder Michael Taylor.

The Jays knew they would not be able to re-sign Halladay, who expressed interest in pitching for a contender.

Rather than letting him walk for nothing, the Jays dealt him to a powerhouse looking to acquire another elite arm.

While with the Phillies, Halladay started an All Star Game, pitched a no-hitter in the 2010 Division Series versus the Cincinnati Reds and a perfect game against the Marlins, becoming the first player in Major League Baseball history to have a no-hitter and perfect game in the same season.

Doc Halladay pitched with the same zeal and finesse that Toronto fans remembered during his tenure in Canada.

Jays fans adored him so much, that upon his return to Rogers Centre on Canada Day in 2011, he received a standing ovation and was greeted with cheers from the fans he thrilled for 11 years in a Jays uniform.

The same cannot be said for the prospects Toronto received from the Phillies in the Halladay trade.

Travis d'Arnaud never played an inning for the Jays, and was one of the highly touted prospects (along with Noah Syndergaard — a.k.a. Thor) sent to the New York Mets in 2012 for reigning National League Cy Young award winner, R.A. Dickey.

Like d'Arnaud, Michael Taylor never played for the Jays and was immediately dealt to the Oakland Athletics for first baseman Brett Wallace.

The centerpiece of the Halladay deal, Kyle Drabek, never lived up to the sky high expectations he brought with him to Toronto.

Drabek, the son of 1990 National League Cy Young award winner, Doug Drabek, compiled an 8-15 record in five seasons with the Jays.

In contrast, Roy Halladay reached eight wins with the Phillies on June 4, 2010 following a victory over the San Diego Padres.

While the Halladay trade exemplifies the risks that come with dealing a franchise player, their rival, the Baltimore Orioles, showed how dealing a franchise player can set a team up for the next decade.

Following the best season of his career in 2007, Orioles pitcher Erik Bedard was dealt to the Seattle Mariners in exchange for a young outfielder named Adam Jones, along with pitchers George Sherrill, Kam Mickolio, Chris Tillman and Tony Butler.

In four seasons with Seattle, Bedard posted a 15-14 record; two more wins than the 2007 season that led the Mariners to deal for him in the first place.

Meanwhile, Adam Jones has gone on to hit the fifth most home runs in Orioles history (240) trailing only Cal Ripken Jr., Eddie Murray, Boog Powell and Brooks Robinson.

Did I mention his four Gold Glove awards? How about the fact he is a five time All-Star? His Silver Slugger award?

Kam Mickolio and Tony Butler never panned out for the Orioles.

George Sherrill was an All Star for Baltimore in 2008.

Chris Tillman has proven to be an undervalued commodity acquired in the Bedard trade.

He's posted a 73-53 mark, and between 2012 and 2016, was one of the most reliable pitchers in the organization.

This season has been a let down for the tall right hander who has spent the season battling a shoulder injury. Tillman is currently 1-5 with a career worst 7.01 ERA.

So there you have it.

Trades can make or break your franchise.

In the next week general managers will have to roll the dice and ask themselves, will one trade make their team better or worse in the long run.

Prospects can either pan out or flame out.

The good news is, if they flame out, they can still become general manager of the Oakland Athletics and have Brad Pitt portray them in an an Oscar nominated film.

How's it going Billy Beane?

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