The current July 31 trading deadline has not always existed in this form. As a result of the 1985 strike on August 6 and 7, the CBA was renegotiated and the current date of July 31 was established for the 1986 season. That CBA negotiation also saw the removal of the interleague trade waiver restrictions, which required any player switching leagues to go through waivers of his current league.
Way back in the dark ages (turn of the 20th century) there was no such thing as a trading deadline. Teams were free to trade, buy and/or sell their players at any point of the season. But as the American and National Leagues were operated separately, there weren't many, if any, interleague trades. And as there were only eight teams per league, the owners were pretty tight and very rarely did shady trades occur.
The National League was the first league to institute a deadline in 1917, choosing August 17. In 1920, the American League finally got around to establishing a date (mainly because of the Babe Ruth purchase), and they chose July 1. But these dates weren't strictly enforced by the league presidents.
On July 23, 1922, the New York Yankees sent Chick Fewster, Elmer Miller, Johnny Mitchell, Lefty O'Doul and $50k to the Red Sox and received Joe Dugan and Elmer Smith. Basically the Yankees sent four backups and cash to get a starting third baseman. On July 30, 1922, the New York Giants traded Larry Benton, Harry Hulihan. Fred Toney and $100k to the Boston Braves for Hugh McQuillan. That would be two minor leaguers, a swing starter and cash for a starting pitcher. After the purchase of Babe Ruth in 1920, these two deals reeked of similar buyouts. Oh and the Giants defeated the Yankees in the World Series that year. Owners that were not in the red were tired of the rich New York owners buying up the top talent.
After the Black Sox scandal in 1919, the leagues joined forces and hired Kennesaw Mountain Landis as the first baseball commissioner. It was late in the 1922 season that the owners got together with Landis and established a new trading deadline date of June 15, based on Pirates owner Barney Dreyfuss input. This June 15 date remained in effect through the 1985 season.
So let's review some of the deadline deals of each of the three eras. I tried to define each trade as Cleveland being a buyer, being a seller, or neither.
I could only locate three deals that seemed to fit those criteria. In 1908, the Naps purchased Cy Falkenberg and Dave Altizer from the Washington Senators for $7k. Neither Falkenberg or Altizer played all that well for the Naps, but the team did finish on a 44-25 run an finished just a half game back of the Tigers.
In 1914, the Naps were 30-61 on July 28 and dealt Vean Gregg to the Red Sox for Fritz Coumbe, Ben Egan and Rankin Johnson. Gregg pitched poorly after the trade (69 ERA+) and although Johnson and Egan didn't do anything, Coumbe stuck with the Indians for six seasons, with 1916 (147 ERA+) and 1917 (132) beign the high points.
But the real steal of a deal happened in 1910. The Philadelphia Athletics led the Yankees by 6.5 games on July 23. But Connie Mack wanted to upgrade his outfield. So the Naps, being 19 games out, traded him Bris Lord for Morrie Rath and a PTBNL. That PTBNL ended up being Shoeless Joe Jackson who played five more stellar seasons with the Indians before being sent to the White Sox.
1923-1985 Buy Mode
I only count eight seasons where the deals qualify as the Indians being buyers, 1948, 1952, 1953, 1954, 1955, 1960, 1972 and 1974. In 1972 and 1974, the Tribe was only 3 games back when the deals were made, but both of them were not major in nature, and the Tribe actually finished well back in the standings.
The best deal probably was the 1948 where in one deal they gave up Al Gettel and Pat Seerey for Bob Kennedy to bolster the bench on June 2. The second deal on June15, netted them Sam Zoldak for Bill Kennedy. Zoldak was 9-6 in 23 games, 12 starts and a 2.81 ERA. While technically not a deadline deal, the Indians also signed Satchel Paige on July 7 that year and he was 6-1 in 21 games, seven starts and a 2.48 ERA. That's signing nudges this one over the next entry. After the Paige signing, Cleveland finished on a 52-30 run.
In 1954, the Indians dealt pitcher Bob Chakales to the Orioles for Vic Wertz. Wertz put up a 275/344/478 122 OPS+ in 337 PA, 14 HR and 48 RBIA after the trade. Chakales finished 3-7 and a 3.73 ERA (96 ERA+) for the Orioles. The Tribe finished 83-30 after picking up Wertz.
The largest deal that qualifies as a buy mode was the 1953 trade with Detroit. The Indians were 10.5 games back, but in second place when they dealt Al Aber, Ray Boone, Steve Gromek and Dick Weik for Owen Friend, Joe Ginsberg, Art Houtteman and Bill Wight. Only Boone panned out for the Tigers while Houtteman was serviceable in the pen. Everyone else was a big meh.
1923-1985 Sell Mode
In 1964, the Indians dealt Mudcat Grant to the Twins and received George Banks and Lee Stange. Banks totaled 33 PA in three seasons. Stange was good in 1965 but ended up being dealt to Boston in 1966 for Dick Radatz.
In 1967, Rocky Colavito was sent to the White Sox to give him a last shot at the playoffs. The White Sox didn't make it. Jim King only had 22 PA before retiring at 34 and Marv Staehle never played for Cleveland, he was sold to the Seattle Pilots.
In 1973, the Tribe made three separate deadline deals with the Royals, Yankees and Tigers, none of which made the postseason. The trade that hurt the most was dealing Steve Mingori to the Royals for Mike Jackson (not that one). Jackson made one single pitching appearance after the trade while Mingori pitched another solid six seasons in Kansas City.
The most famous Sell deal though is the 1984 trade of Rick Sutcliffe, Ron Hassey and George Frasier to the Cubs for Joe Carter, Mel Hall, Don Schulze, and minor leaguer Darryl Banks. While Sutcliffe won the Cy Young that year for Chicago, going 16-1 and a 144 ERA+ after the trade, the Tribe made out by hitting on Carter. Carter had six pretty decent years in Cleveland before being flipped into Sandy Alomar and Carlos Baerga.
In 1958, the Indians made a deal with the Royals that netted them Woodie Held and Vic Power for Roger Maris, Dick Tomanek and Preston Ward. While most point to this being a bad deal as Maris ended up with the 61 homers for the Yankees in 1961, Held actually had a very good career in Cleveland. His power from the shortstop position was very uncommon and he was pretty good for us.
In 1968, the Indians swapped Leon wagner to the White Sox for Russ Snyder. Both played well after the deal. But the Tribe lost on the Vic Davalillo trade for Jimmie Hall with the Angels.
In 1975, the Indians traded another Cy Young pitcher away, Gaylord Perry. The Indians ended up winning this deal in the long run, but also did well in the short term. Jim Bibby was effective in his three seasons. Rick Waits pitched in Cleveland for nine seasons before heading to Milwaukee in a deal for Ernie Camacho. But the jewel of this trade was Jackie Brown? Yes, Jackie had a robust 83 ERA+ in his 57 games here, but he ended up netting us Andre Thornton from the Expos.
In 1979, the Tribe dealt Paul Dade to the Padres for Mike Hargrove. That was definitely a win. They also dealt Don Hood for Cliff Johnson from the Yankees. That trade worked for both sides in 1979.
1986+ Buy Mode
In the 1994 strike season, the Indians traded Steve Farr and Chris Nabholz to the Red Sox for Jeff Russell. Neither team won this trade as all had 5.00 ERA or higher afterwards.
In 1995, Ken Hill was acquired from the Cardinals for David Bell, Rick Heiserman and minor leaguer Pepe McNeal. Cleveland won this trade as Hill had a tremendous Aug/Sept and also pitched well in the postseason. None of the three traded away did anything for the Cardinals.
In 1996, three separate deals occurred: Jim Poole to the Giants for Mark Carreon, strictly a role player; Eddie Murray to the Orioles for Kent Mercker, Mercker took Poole's spot in the pen; and Carlos Baerga and Alvaro Espinoza to the Mets for Jeff Kent and Jose Vizcaino. That last deal still confuses me as both Kent and Vizcaino left after the season for Matt Williams. Were those the guys that San Francisco had already targeted? But also recall, Kent didn't become All-Star Kent until hitting behind Bonds.
In 1997, they traded Steve Kline to the Expos for Jeff Juden. Kline would go on to have a decent career, Juden, not so much. They also dealt four players (including Danny Graves) to the Reds for John Smiley and Jeff Branson. Smiley was injured shortly after the trade and out of baseball quickly. A bad outcome to be sure on this one.
In 1998, they sent Eric Plunk to the Brewers to bring back old fan favorite Doug Jones. This worked for both sides that year. They also sent Shawon Dunston, Jose Mesa and Alvin Morman to the Giants for Jacob Cruz and Steve Reed. Both lasted with the Tribe until 2001 when they were separately traded for Jody Gerut and John Rocker respectively.
In 2001, Zach Day was sent to the Expos for Milton Bradley. Even though Bradley was a head case, that trade was a win for the Indians.
In 2011, three deals ensued because the Tribe was only 1.5 games out. Kosuke Fukadome was picked up from the Cubs for two minor leaguers, Abner Abreu and Carlton Smith. A win for the Tribe, as neither played for the Cubs or are even still in their farm system. Orlando Cabrera was sent to the Giants for Thomas Neal. Nobody wins that one. But there was the biggie of course where four prospects, top prospects Drew Pomeranz and Alex White, prospects Matt McBride and Jo Gardner for schizophrenic Ubaldo Jimenez. Right now, the Indians technically win this trade because Ubaldo, while awful a lot of the time, still has made almost every turn in the rotation since the trade. If his recent streak continues, it won't take much to take the "technically" out of that sentence. Although the Rockies still have a chance of it working in their favor too, as they have control of each for quite a bit still.
1986+ Sell Mode
The Indians dealt Tony Bernazard to the A's in 1987 for Darrel Akerfelds and Brian Dorsett. Neither Akerfelds or Dorsett did much. They also traded an old and ineffective Steve Carlton to the Twins for minor leaguer Jeff Perry. Carlton was even worse for the Twins and Perry never played in Cleveland.
In 1991, free agent to be Brook Jacoby was traded to the A's for Lee Tinsley and Apolinar Garcia. Neither Garcia or Tinsley ever played for the Indians. Jacoby played terribly for Oakland before re-upping with the Indians in the offseason.
In 1992, Alex Cole was sent to the Pirates for Tony Mitchell. Mitchell never made it to the bigs and Cole was effective as a role player for Pittsburgh. A better deal did happen, but really wasn't a sell mode trade. Kyle Washington, was sent to the Orioles for Jose Mesa, most likely because Mesa was out of options. That deal worked out pretty well, all thing considered.
By the early 2000's, a rebuild was definitely necessary. In 2002, four deadline deals were made. Chuck Finley was first to be moved, heading to the Cardinals for Luis Alfonso Garcia and a PTBNL. While Garcia never made the majors, the PTBNL ended up pretty good, Coco Crisp. Indians won that deal. They also sent backup Jolbert Cabrera to the Dodgers for Lance Caraccioli. Yeah, the Dodgers won that one. Six days later, Paul Shuey went to LA as well for Francisco Cruceta, Terry Mulholland and Ricardo Rodriguez. That deal is a wash. Finally, the last sell piece was infamous Ricardo Rincon to the A's for Marshall McDougall. The A's definitely won that one.
In 2005, Alex Cora was set to the Red Sox for Ramon Vazquez. A trade of backups rarely results in a win for either, but rather a meh-meh. Gerut was also dealt at the deadline, although it wasn't a "sell mode" as the Cubs were 13 back. The Tribe received Jason Dubois back.
In 2006 there were four more deadline deals. The first, while made with the first place Padres, really isn't a sell mode either as the Indians sent minor leaguer Mike Adams for Brian Sikorski. Adams would go on to have a very productive few seasons while Sikorski did not. Bob Wickman was sent to the Braves for Max Ramirez. Wickman stopped his heart inducing outings while in Atlanta, 18 saves and a 1.04 ERA (434 ERA+) while Ramirez turned into the feel-good story in 2007, the coming home of Lofton. Ben Broussard was packaged for Shin-Soo Chin and PTBNL Shawn Nottingham. Huge win for Cleveland here. The last deal involved Ronnie Belliard going to the Cardinals for reserve infielder Hector Luna. No real winner there.
The 2008 deadline is highlighted by the CC Sabathia trade to Milwaukee. While the main paice, Matt LaPorta has flamed out, Zach Jackson was nothing to write home about, and Rob Bryson is still fighting the injury bug, this deal looks like a huge loser. However, in the deal was the infamous PTBNL. That player turned into Michael Brantley who while not All-Star caliber, has become an integral part of the outfield and lineup for the Indians. As CC was gonna walk no matter what, I still call this trade a win even though the main chip flamed out because of Brantley's success.
But wait, there were two other 2008 deals. The first was Luis Perdomo to the Cardinals for Anthony Reyes. Nothing panned out for either side here. But the second deal was Casey Blake for Carlos Santana and Jon Meloan from the Dodgers. This is another huge win on Cleveland's side, even with Santana's defensive deficiencies.
2009 was very similar to 2008 as there multiple players on the way out. Rafael Betancourt went to the Rockies for Conor Graham. The Rockies obviously win this as Betancourt is now their closer and Graham was cut in 2011. Ryan Garko headed to the Giants for Scott Barnes. I call this a slight win as Barnes still has a chance to become useful.
And then there was the first biggie, Cliff Lee and Ben Francisco to the Phillies for Carlos Carrasco, Jason Donald, Lou Marson and Jason Knapp. Even though Lee ended up moving on to Texas and Seattle before returning to the Phillies, the Tribe loses this deal big time. Donald has moved on. Marson looks to have been passed by Gomes. Knapp is still a sore spot between Amaro and Antonetti as he has never been healthy. Carrasco still has the stuff to be useful, but the Phillies made the World Series with Lee's help. He was 7-4 in 12 starts, a 3.39 ERA, 124 ERA+ and won all four of his postseason starts that year.
That was only a prelude to another massive trade. This one involved the Red Sox as Victor Martinez was dealt for Justin Masterson, Nick Hagadone and Bryan Price. Price reached AAA this year. Hagadone has been shuttling between Columbus and Cleveland and could still be a good bullpen arm. But Masterson has turned into everything that was hoped for by Antonetti and company. A win for the Tribe here even though Victor hit like gangbusters for them in 2009 and 2010 before moving onto Detroit as a free agent.
The 2010 season is the last year we were sellers. Jhonny Peralta moved to Detroit for Giovanni Soto. Detroit obviously won that trade and is why I doubt we'll many more intra-division deals. Austin Kearns was sent to the Yankees for Zach McAllister (PTBNL). Kearns was not that good in his backup role there. He actually re-upped with Cleveland that offseason. And McAllister has become a decent rotation arm. The next day, the Tribe also dealt Kerry Wood to the Yanks for two minor leaguers, Matt Cusick and Andrew Shive. Wood did very well in his setup role, 2-0, 0.69 631 ERA+ in 26 innings. Neither Cusick or Shive even appeared in a minor league game for the Tribe. The last deal was a three team deal where Jake Westbrook headed to the Cardinals and the Tribe got back Corey Kluber from the Padres. I think this turned into a win for the Tribe as well. It is also interesting to note that the Yankees were the only team of the four to make the playoffs, Detroit, San Diego and St. Louis all missed the postseason that year. The Yankees made it as the wild card.
In 1990, the Indians won a trade where they sent Tom Lampkin to the Padres for Alex Cole. Lampkin only netted a 57 OPS+ while Cole had a 109 OPS+ and 40 SB after the trade.
In 2000, the Tribe made three separate deals at the deadline. The big one was Richie Sexson, Paul Rigdon, Kane Davis and a PTBNL to the Brewers for Bob Wickman, Jason Bere and Steve Woodard. The PYBNL turned out to be Marco Scutaro (!). This trade actually worked for both teams fairly well. They also traded backup outfielder Alex Ramirez and Enrique Wilson to the Pirates for Wil Cordero. The Tribe wins that one by default. The last deal was sending Ricky Ledee to the Rangers for David Segui. The Indians definitely won that trade.
The last season I've identified here is 2003. Aaron Myette was sent to the Phillies for Lyle Mouton. Two weeks later, Ricardo Rodriguez and Shane Spencer headed to Texas for Ryan Ludwick. Neither deal panned out for any of the teams involved.
All in all, I think Cleveland has done fairly well overall in all of the deals thy have made. The obvious choice for best deal ever is the Colon deal, but that was not a technically a July deal so it isn't here. I'd rank the Sutcliffe deal the tops as it netted us Carter and then by chain, Alomar and Baerga. Personally I'd rank the Shoeless Joe Jackson deal number two, but it technically is not a deadline deal as there was no deadline. And I actually like how the 2010 deals have panned out. Getting Kluber and McAllister for Westbrook and Kearns is pretty good.