Boston Sports Extra

Following up my article covering the best trade deadline deals in franchise history, this article goes over the worst ones the team has ever made. The top worst trade can probably be guessed, as it is an iconic trade, but what comes after that?

1. Jeff Bagwell for Larry Andersen

With the Red Sox in the playoff hunt, they wanted to shore up their bullpen. So, they acquired Larry Andersen from the Astros in August. Larry Andersen was a good reliever, going 5-2 with a 1.95 ERA for Houston before the trade. Andersen did his job in Boston, pitching to a 1.23 ERA over 22 innings pitched as the Red Sox won the division. In no way does he deserve the bad name recognition that came with this trade, he did his job exceptionally well.

The problem is, Jeff Bagwell became a Hall of Famer. August trades don’t usually yield that much value, yet alone a prospect like Bagwell who was ranked 32nd in baseball at the time. He was walking a bunch and hitting a lot of doubles in the cavernous field at Double-A New Britain. Bagwell had an .880 OPS as a 22 year old at the time of the trade.

Here’s the worst part; the Astros asked for several other players before getting to Bagwell. Pitching prospect Kevin Morton, who had a fantastic Major League debut, was one. He never did much after the debut. Scott Cooper was another third base prospect the Red Sox for some reason preferred to Bagwell; oops. At least Mo Vaughn became a fan favorite and an MVP winner. But Phil Plantier, Daryl rvine and Dave Owen are others the Astros were rumored to maybe have taken in return.

2. Freddy Sanchez for Jeff Suppan

This trade doesn’t get as much publicity as some of the other bad moves, but it’s arguably worse. The deal also had more moving pieces, but it was essentially Freddy Sanchez and cash for Jeff Suppan. A little over a week earlier, the Red Sox had traded Brandon Lyon and Anastacio Martinez to the Pirates for Mike Gonzalez and Scott Sauerbeck.

When a problem was found in Brandon Lyon’s physical, the two teams tried to work things out to make it right. Lyon and Martinez were traded back to the Red Sox along with Suppan for Sanchez, Mike Gonzalez and cash. They essentially just swapped everyone back, with cash replacing Scott Sauerbeck. If you included those pieces in with the trade, it would get even worse for the Red Sox, as Mike Gonzalez had a better career than anyone the Sox got.

As for the main pieces, Jeff Suppan was having his best season to date, pitching in the National League Central. However, reacquired by the Red Sox who he had started his career with, Suppan’s pitching reverted back to where it was during his first stint with the team as a youngster. He posted a 5.57 ERA, 1.43 WHIP and only 4.6 strike outs per nine innings over 10 starts and one relief appearance for the Red Sox. He wasn’t even used in the postseason.

Freddy Sanchez, who was the Red Sox top prospect at the time of the trade, went on to become a batting champion. He hit .291 as a rookie in 2005, then led the league in hitting in 2006 with his .344 average. He was an All-Star in 2006, 2007 and 2009. Meanwhile, the Red Sox kept shuffling through shortstops and second basemen for a few seasons after the trade, both positions Sanchez could have played.

Freddy Sanchez won the batting title in 2006 and made three All-Star Games in a four year stretch for the Pirates. Jeff Suppan fared so poorly he didn’t pitch in the postseason.

3. David Murphy, Kason Gabbard & Engel Beltre for Eric Gagne

This is mostly due to how bad Eric Gagne was for the Red Sox, as two of the players traded didn’t do a lot. It is kind of surprising they had to give up this much though, as David Murphy was a former first round draft pick and Kason Gabbard, although he didn’t possess great stuff, was 4-0 with a 3.73 ERA for the Red Sox that season. Including the season before, Gabbard had a 3.65 ERA over 11 starts and three relief appearances for the Red Sox. He didn’t pitch as well in Texas however, going 4-4 with a 5.14 ERA over 20 starts the next two seasons.

David Murphy turned into a solid outfielder in Texas. From 2008-2013, his average season was .283 with 14 home runs and a .795 OPS over 425 at-bats. He often didn’t play against lefties, leading to the average of just 425 at-bats. 2012 was his best season, as he batted .304 with 15 homers and an .859 OPS.

Eric Gagne was coming back from injury that season, having thrown just 15.1 innings over the previous two seasons. He was pitching well in Texas, going 2-0 with a 2.16 ERA and 16 saves. It all came unraveled in Boston, and it never came back. In 20 games the rest of the way, Gagne pitched to a 6.75 ERA and 1.88 WHIP over 18.2 innings. He gave up three more runs in 4.1 postseason innings. Generally, you could count on him to give up a run or two.

Boston, MA – 08/14/07 – Sox reliever Eric Gagne enjoyed little to no success in Boston. (Barry Chin, Globe Staff) Section: Sports, Reporter: Amalie Benjamin, slug: 15redsox.

4. Ty Buttrey & Williams Jerez for Ian Kinsler

The 2018 Red Sox, historically great as they were, had a need for some relief help. It was odd they had a guy like Buttrey, throwing 100 and dominating in Triple-A, left down in the minors while others got turns to help the bullpen. It was more baffling still when he was traded, along with another minor leaguer, for an over-the-hill second baseman.

Buttrey was called up to the Angels pretty soon after the trade. Since getting the call, he has been used in late innings by the Angels as one of their top setup men, sometimes going more than an inning at a time. His blazing fastball has led to 10.7 strike outs per nine innings pitched. The Red Sox could certainly use a guy like him in their bullpen.

Williams Jerez should have been almost enough for an aging free agent. He had a 3.63 ERA and struck out 69 batters over 52 innings in Triple-A. He’s pitched three innings at the big league level so far this season. Jerez and one other guy of lesser talent should have done the trick for Kinsler, who was an unnecessary add anyways.

Ian Kinsler was 36 years old at the time of the trade. He had batted .236 in 2017, and was hitting .239 for the Angels in 2018. His bat speed was gone, which was painfully noticeable in the playoffs when he swung and missed at fastballs all postseason long. He hit .242 with a home run for Boston in the regular season, then batted .206 with 14 strike outs in 34 at-bats in the playoffs.

Yes, the Red Sox won the World Series, but they would have won it without Kinsler. He didn’t add anything. They would have cruised to victory with the guys they had been going with, or with Brandon Phillips, who they had signed midseason. In fact, they might have swept the World Series with a different second baseman. His error in the 13th inning of game 3 directly led to a blown lead in an eventual loss. This is one of their worst deadline trades.

Ty Buttrey seems to have hit a wall of late, which can happen to rookies often. However, his ERA was well below 3.00 a week ago as he was pitching in dominant fashion.

5. Curt Schilling & Brady Anderson for Mike Boddicker

This trade is much higher on most people’s lists, but I think it is judged unfairly. It is one-hundred percent, long-term hindsight that makes this a bad trade.

The Red Sox traded for Mike Boddicker in 1988 on their way to a playoff appearance. He went 7-3 with a 2.63 ERA for them the rest of the way. Boddicker would spend two more years as the Red Sox number two starter behind Roger Clemens. After winning 15 games in 1989, Boddicker went 17-8 with a 3.36 ERA over 228 innings pitched in 1990 while winning the Gold Glove. He was a good pitcher for Boston. His totals in Boston were a 39-22 record with a 3.49 ERA.

But, they gave up Curt Schilling, who should be in the Hall of Fame and is one of the all-time greatest postseason performers in the history of the sport. They also gave up Brady Anderson, who was a good prospect putting up some high on-base percentages in the minor leagues. Steep price to pay, but for a top starter that’s generally the price.

Here’s the other kicker for me, the part that makes this unfairly judged. This trade took place in 1988, neither Schilling nor Anderson broke out until 1992, four years later. Boddicker was already gone from the Red Sox. At the end of his tenure in Boston, this trade would have been considered a big win.

From 1988-91, Anderson batted .219 with 10 home runs in the big leagues. He broke out with 21 home runs and 53 stolen bases in 1992 and went on to a fine career that saw him hit 209 home runs and steal 307 bases for the Orioles. But by 1992 when he broke out, who’s to say the Sox wouldn’t have traded him in another deal by then?

As for Schilling, he was traded again, twice! After showing nothing for two years, Schilling had some success in 1990 out of the bullpen. He was then traded to the Astros before 1991, where he was mediocre in relief. He was then traded again, straight up for Jason Grimsley of all people. It’s then, with the Phillies, where he broke out in 1992. That season he had a 2.35 ERA and led the National League in WHIP.

At the end of the day, this is on the list, but in the last spot, because of the players Schilling and Anderson eventually became. This trade catches way too much flak though.

Mike Boddicker was 39-22 with a 3.49 ERA over 2.5 seasons for Boston.

Feature image from HouseofHouston.com

The higher the numbers get, the less they have been worn. As we enter the fifties, the amount of players to select from, and generally the quality of players lessens. That is not to say these guys did not have their value, but you might not find yourself remembering who wore these numbers.

Number 51 – Daniel Bard

After wearing number 60 as a rookie in 2009, Bard switched to the number 51. He had his best career season in 2010.

Daniel Bard threw easy heat; He didn’t look like he was exerting much effort, but the ball would fly out of his hand at 98-100 miles per hour. He also had a nice slider to go with it, giving him a devastating two-pitch combination out of the pen.

This repertoire was at its best in that 2010 season, as Bard posted a 1.93 ERA and 1.00 WHIP as the Red Sox top setup man to Jonathan Papelbon. Bard was dominating again the next season until September, when he collapsed along with the rest of the team. At the end of August, Bard had a 2.03 ERA with batters hitting .164 against him. That includes an opening day disaster that saw him allow four runs. Between his second game of the season and the end of August, Bard had a fantastic 1.47 ERA. However, September saw him allow more runs than he had allowed from April 5th through the end of August and his ERA finished at 3.33.

The Red Sox decided to try Bard in the rotation in 2012, which made zero sense. Bard had begun his minor league career as a starting pitcher and was a disaster, prompting the move to the bullpen. This time didn’t go any better. Bard had a 6.22 ERA and never recovered. He spent most of the next several years throwing pitches to the backstop and hitting batters in the minor leagues. However, he was still a dominant setup man for a couple seasons wearing number 51.

Honorable Mention: Reid Nichols

Number 52: Mike Boddicker

The Red Sox traded Brady Anderson and Curt Schilling to the Orioles for Boddicker at the trade deadline in 1988 to bolster their rotation for the stretch run. Although Schilling ought to make the Hall of Fame, he wasn’t a starting pitcher until 1992. Brady Anderson was also a fine player, but hadn’t done anything before 1992 as well. That is four years later, had the Red Sox not traded them then, they very well could have moved on later before they amounted to anything anyways.

Mike Boddicker did his job for the Red Sox. Over the rest of the 1988 season he was 7-3 with a 2.63 ERA. He gave the Red Sox three very good starting pitchers and they won the American League East.

Boddicker pitched two more seasons for the Sox, winning 32 games. In 1990, he had his best season since 1984, going 17-8 with a 3.36 ERA. He also won the Gold Glove Award that season. He made a team high 34 starts, throwing 228 innings. In two-plus seasons with the Red Sox, Boddicker finished 39-22 with a 3.49 ERA.

Honorable Mention: Eduardo Rodriguez

Number 53 – Rich Hill

Rich Hill is not someone you would expect to find on a list like this for the Red Sox. He was very successful, but in a limited amount of innings while with the franchise.

Hill wore the number 53 with the Red Sox between 2010 and 2012. During this time he had been transitioned into a relief pitcher after a couple ineffective seasons and a torn labrum. The Red Sox signed Hill at the end of June in 2010 and made him a September callup. He pitched four shutout innings.

The next season Hill was given an opportunity out of the bullpen in May. Using a new sidearm motion, Hill was dominating, throwing eight shutout innings and striking out 12 batters before hurting his arm again. This time he would need Tommy John Surgery.

Back with the club in 2012, Hill recovered quickly enough to pitch for the team before April was over. However, another injury sidetracked his season until September. When the season was over, he had gone 1-0 with a 1.83 ERA 19.2 innings.

In total wearing number 53 for the Red Sox, Rich Hill was dominant in limited innings due to injury. He finished 2-0 with a 1.14 ERA and over a strike out per inning during this time. When he dominated in September of 2015 for the Red Sox, he was wearing a different number.

Honorable Mentions: Tomo Ohka, Brendan Donnelly, Chad Bradford

Number 54 – Darnell McDonald

Darnell McDonald is another surprising addition to this lineup of players. McDonald had one pretty good season as a part-time player for the Red Sox, and that’s enough to make him the best number 54 in team history.

McDonald was a first round pick way back in 1997, but only had 147 career Major League at-bats when the Red Sox signed him for the 2010 season. He would more than double his career at-bats that season. Over 117 games and 319 at-bats, McDonald hit nine home runs and stole nine bases in ten tries. He had a respectable .270/.336/.429/.766 batting line.

McDonald made an immediate impact on that 2010 team. In his first at-bat with the Red Sox, he pinch-hit for Josh Reddick in the bottom of the 8th inning, trailing by two with a runner on base. McDonald hit a two-run homer off Darren Oliver to tie the game at six. The Red Sox would win it the next inning when Darnell McDonald drove home the winning run with a base hit to center field.

McDonald’s stint with the Red Sox wasn’t as successful after that season. He batted .236 with six home runs in 2011 and would be released during the 2012 season after a poor start. His 2010 season was more than any other number 54 had to offer though.

Honorable Mention: Morgan Burkhart

Number 55 – Joe Hesketh

Joe Hesketh was a left-handed pitcher for the Red Sox from 1990-94. He mostly started but also relieved some with the team. He had one good season, a couple alright ones and one poor one, which is enough to get him the spot at 55 without anyone else even putting up a fight.

Hesketh was signed by the Red Sox off waivers on July 31, 1990. By 1991, he was a key member of the pitching staff. That season, Hesketh made 39 appearances, 17 of which were starts. He finished 12-4 for an American League best .750 winning percentage. He entered the starting rotation around midseason and went 10-3 with an ERA of 3.00 in the second half of the 1991 season. Hesketh had a 3.29 ERA on the season.

The next season he was mostly a starter, finishing 8-9 with a 4.36 ERA. After a poor 1993 season that saw him pitch mostly out of the bullpen, Hesketh rebounded for 1994. In that strike-shortened season he was 8-5 with a 4.26 ERA over 20 starts and five relief appearances. In total he was 31-26 with a 4.04 ERA with the Boston Red Sox.

Featured picture from Sports Illustrated