The 2014 trade deadline is less than two weeks away. It remains to be seen if the Cleveland Indians will make any moves this summer, and whether the team will be buyers or sellers if it does make any moves. Any trade comes with risks; this is the nature of sports, particularly in baseball. There is no crystal ball to tell you what prospects will or won’t bust, or what veteran will put you over the top. The Indians have made several trade deadline deals over the years with both great success and major disappointment.

For the sake of this article, I’m counting any deals made in June, July, or August as the “trade deadline” period. I avoided some of the most recent deals, preferring to leave a five-year window on trades. For example, I left off the Ubaldo Jimenez trade as we still don’t know how that will look in the end. At first, that trade looked terrible, but then Ubaldo had a great 2013 and led the Indians to the playoffs. Meanwhile the prospects dealt to Colorado have all struggled. But Drew Pomeranz still has potential, and for all I know he could make the Hall of Fame one day.

Drew Pomeranz pitching for Oakland. Credit: Richard Mackson-USA TODAY Sports

Trades that seem bad at one time can quickly change in the favor of another. The CC Sabathia trade looked terrible for a while but now it’s netted the Tribe an All-Star whom they control for several years in Michael Brantley. Here are the five worst trade deadline trades in Indians history, listed in chronological order (for the most part) :

July 31, 1997: Indians trade RHP Danny Graves, INF Damian Jackson, LHP Jim Crowell & RHP Scott Winchester to the Cincinnati Reds for LHP John Smiley & INF Jeff Branson.

Smiley was the main target for the Tribe in this deal. Cleveland liked its offense but felt its rotation could use a boost. However, Smiley was really struggling in Cincinnati leading up to the trade, posting a 5.23 ERA in 20 starts. Cleveland hoped Smiley could rebound to 1996 levels when he had a 3.64 ERA; however, he made just 6 starts for the Tribe before blowing out his arm with a career-ending injury. Branson was an OK bench guy in 1997, but barely got his OPS over .500 in 1998, his final year with Cleveland. Graves was only a reliever but managed to make two All-Star teams with the Reds and had a solid career. Jackson was at one time a top spec but ended up as a utility guy, though at times a damn-solid one. In terms of losing much,the Tribe lucked out here but gave up a lot of solid (at the time) trade assets to get a damaged pitcher and utility infielder.

July 28, 2000: Indians trade 1B Richie Sexson, RHP Kane Davis, RHP Paul Ridgon & a PTBNL (INF Marco Scutaro) to the Milwaukee Brewers for RHP Jason Bere, RHP Bob Wickman & RHP Steve Woodard.

Marco Scutaro once a throw-in, now an All-Star 2B. Credit: Chris Humphreys-USA TODAY Sports

Sexson was coming off a 31 HR, 116 RBI, .818 OPS season. He struggled in the early going of 2000 but turned things around quickly after the trade hitting 133 HR over the next three-and-a-half seasons. Scutaro was the player to be named later and while at the time his inclusion seemed harmless, he turned into a good player, even becoming an All-Star. Wickman was a solid closer but nothing special as his WHIP only managed to get under 1.40 twice, in addition to missing the entire 2003 season with injury. Bere was supposed to be the prize of this deal but had an ERA over six (6.63) and WHIP of 1.675 in half of a season with the Tribe before becoming a free agent (Bere would later make the final two starts of his career with Cleveland in 2003). Woodard was slightly better as he “only” had an ERA of 5.67 in 2000 before becoming a long man/spot starter in 2001, where he still had an ERA over 5 and WHIP over 1.50. He was released following the season.

June 22, 2001: Indians trade RHP Steve Karsay & RHP Steve Reed to the Atlanta Braves for LHP John Rocker & INF Troy Cameron.

Seeing three relievers involved in this trade may make some say “oh well” to themselves, but Rocker was terrible in his lone half-season in Cleveland. He posted a 5.45 ERA, 1.673 WHIP and 6.5 BB/9. Why this trade was even made is a head-scratcher. Sure, another lefty in the bullpen is always nice (Ricardo Rincon and Rich Rodriguez were the two lefties in Cleveland’s pen), but Rocker wasn’t good the year before, as a nice 2.89 ERA masked his horrendous 1.698 WHIP and 8.2 BB/9 ratio. Meanwhile, Karsay had a 1.25 ERA, 1.87 FIP, and a 0.854 WHIP at the time of the trade. This was after back-to-back solid years out of the Tribe pen where he racked up more than 150 innings. Karsay alone was too much to give up, but the Tribe threw in the side-arming Reed as well, who while not anything special, was having a decent year with a 3.62 ERA and 1.171 WHIP.

Cliff Lee is still one of the top pitchers in baseball 5 years after being traded by the Indians. Credit: Bill Streicher-USA TODAY Sports

July 29, 2009: Indians trade LHP Cliff Lee & OF Ben Francisco to the Philadelphia Phillies for RHP Carlos Carrasco, RHP Jason Knapp, INF Jason Donald & CA Lou Marson.

I wanted to leave this deal out as it still hasn’t been a full-five years since the deal was made, but didn’t think one week would change where this deal ranks. I have defended this trade for so long now, but trading the previous year’s Cy Young winner needs to net you more than one bullpen arm, which is all the Tribe has really gotten out of this deal. At least Donald was able to be flipped in the Shin-Soo Choo/Trevor Bauer deal, but Knapp’s injury was bad and Marson never developed to be even a backup catcher (injuries hurt him too, though). Meanwhile Lee continued to pitch like he had in 2008 and the first half of 2009, and has been one of the best pitchers in baseball since this trade. The return seemed light at the time, but even worse looking back.

August 31, 1996: Indians trade OF Jeromy Burnitz to the Milwaukee Brewers for INF/DH Kevin Seitzer:

So I said these would be in chronological order… mostly. I just wanted to save this trade for last as I feel it is by far the worst summer/trade deadline deal in Indians history …

To fully understand how bad this trade was, consider this: the Tribe traded Paul Byrd, Jerry Dipoto, Dave Mlicki and Jesus Azuaje to the New York Mets to get Burnitz and Joe Roa less than two years prior this trade. Burnitz was a former first-round pick of the Mets in 1990 and was a top 50-prospect in all of baseball heading into the 1992 season per Baseball America. The Indians gave up a lot to get him, and it appeared to pay off as in 1996 Burnitz was batting .265/.377/.470 with 7 HRs in 200 at bats for the Tribe. But General Manager John Hart decided the team needed a veteran right-handed bat on the bench and moved Burnitz for Seitzer.

As this trade was after the July 31st non-waiver deadline, Seitzer had to be put on waivers and passed over by every AL team before the Indians could even make the trade. Seitzer played well in the month of September, batting .386/.480/.542/1.022 with a HR and 16 RBI in only 98 plate appearances. However, he was terrible in 1997, and after getting just one plate appearance in the entire World Series he retired from the game. From 1997 to 1999 Burnitz had an OPS over .900 and averaged over 32 HR per season (numbers better or right on par with what David Justice, whom the Tribe traded for a couple months later, had over that same span).

Burnitz for Seitzer may not only be the worst deadline trade the Indians have made, but also one of the worst in baseball history, as ESPN’s Take 2 listed the deal as one of its 15 worst deadline deals in baseball history.

So here you have it, the five worst deadline trades in Indians history. Not everyone will agree on what were the “worst” deals, as each person has their own unique take on trades. For example, Jim Ingraham, beat writer for the Tribe, once listed the Sexson-Wickman deal as one of the best deadline trades in Tribe history; whereas, I listed it as one of the worst here. ESPN’s Take 2 also listed another Tribe trade among its worst deadline deals – the David Justice for Rickey Ledee trade. However, that deal of course also brought over Jake Westbrook who had a rather fine career in Cleveland (and later netted the Indians Corey Kluber). In any case, be sure to check back on Wahoo’s on First for the five best trade deadline deals in Cleveland Indians history, and please feel free to let us know if there are any deadline trades that I missed and why you feel they are among the worst in Tribe history.