A lot of fans in the Nation were disturbed about the signing of right-handed pitcher Jason Marquis before the 2015 season started. There were concerns about his age, his durability and a history of injuries. It may have been a low-risk signing ($1.5 million) but Marquis eventually was released by the Reds after going 3-4 this year and posting an ERA of 6.46. And that earned run average was definitely in Eric Milton territory (see below).

There were a lot of warning flags before this signing of Marquis by Walt Jocketty and the Reds. It was one that didn’t work out. The Marquis signing in itself didn’t lead to the Reds ultimately collapsing this season, but rather it’s symbolic of the organization’s belief it could seriously contend in 2015.

It certainly isn’t the first time it’s happened. Historically, the Reds — like other teams — have made pitching transactions either by trade or free agent signings that have crashed and burned. Most of them have the same characteristics — aging veterans, a questionable history of injuries and durability — and they didn’t pan out.

There are times the farm system can produce or the Reds can make a decent trade for quality pitching. That’s been proved with the successful trades of Fred Norman, Tom Seaver, Danny Jackson, John Smiley and Bronson Arroyo over the years. Sometimes, the Reds get it right.

But sometimes, it just doesn’t work out. Best laid plans are blown up.

It didn’t work out for the Reds and Jason Marquis. And it didn’t work out for the ones listed below. Some of the names you will recognize. Others you won’t. But in the end, the Reds were damaged by the transaction.

Here we go, in no certain order:

Milt Pappas

Probably the most famous “failure” because he was traded for Reds superstar Frank Robinson. Sure, Jack Baldschun and Dick Simpson were included in the deal with Baltimore, but Pappas was the main guy the Reds acquired. Pappas pitched for the Reds  for two-plus seasons before being jettisoned to the Atlanta Braves. Nicknamed ‘Gimpy’ Pappas was a control specialist and innings-eater. He pitched  over 200 innings in each of his two full seasons with the Reds with records of 12-11 and 16-13. Milt Pappas was a good pitcher, but not a great one. He pitched every fourth day for the Reds and was reliable but he couldn’t measure up to Robinson’s Triple Crown performance in 1966. But who could? He was also outspoken. Pappas later admitted to “throwing nothing but fastballs to Roger Maris” when Maris hit his 59th home run of the 1961 season off Pappas, later justifying it because he didn’t agree with Commissioner Ford Frick stating an asterisk should be used if Maris broke Babe Ruth’s record. He continues a decades-long feud with Umpire Bruce Froemming over a walk to Larry Stahl that ruined Pappas’ perfect game against the Padres with two out in the 9th inning of his no-hitter. Pappas was traded to the Braves in June 1968 for a package of players that included reliever Clay Carroll. Getting Carroll, who is in the Reds Hall of Fame, at least gave a little return of the trading of Frank Robinson.

Woody Fryman

Fryman’s fate was worse that what befell Pappas. He was swapped to the Reds along with relief pitcher Dale Murray for beloved slugger Tony Perez and reliever Will McEnaney in probably the worst trade ever made by Bob Howsam before the 1977 season. Fryman arrived to the Reds at the age of 35 (strike one) and was a lefthanded pitcher. The highlight of his brief Reds career was when he won on Opening Day in 1977 against the Padres, thanks to Cesar Geronimo (two-run homer) and Rawly Eastwick (three shutout innings of relief) Fryman clashed with Reds Manager Sparky Anderson (strike two) repeatedly. Sparky pulled him from the starting rotation in June. Fryman then stunned the Reds by announcing his retirement (strike three) in the middle of a heated pennant race against the Dodgers. Howsam traded Fryman to the Cubs immediately after the season for Bill Bonham and Fryman resumed his career. A Kentucky native and tobacco farmer, Fryman is in both the Montreal Expo and Kentucky Sports Hall of Fame. His record with Cincinnati in 1977 was 5-5, with an ERA of 5.38– not much of a return for a future Hall of Famer in Tony Perez. Howsam really blew this one.

Eric Milton

This was the worst free-agent signing ever by the Cincinnati Reds. The Reds signed Milton to a three-year $25 million contract on December 28, 2004. Merry Christmas, Reds fans. Milton was similar in style to Jim Merritt, a lefty who was a 20-game winner for Cincinnati in 1970. Unfortunately, Milton needed perfect control because he had mostly ordinary stuff. Milton gave up a staggering 40 home runs in 2005, to accompany his 8-15 record and an ERA of 6.47. That’s right— 6.47. He improved slightly in 2006 (8-8, 5.19) but tore a cartilage in his left knee. In 2007, he was 0-4 when he had Tommy John surgery. And that was that for Eric Milton, his career with the Reds and $25 million.

Roger Nelson

The Big Red Machine was always on the look out for starting pitching. Before the 1973 season, Howsam traded Hal McRae and Wayne Simpson to the Kansas City Royals for Nelson and outfielder Ritchie Scheinblum. The Reds had no room for McRae, a promising young righthanded hitter. McRae’s liability was his lack of defense and speed. He was the perfect DH, hence the trade to the American League. He certainly was a good one for KC and McRae wound up in the Royals Hall of Fame. For Roger “Spider” Nelson, it didn’t quite work out with the Reds. Nelson was a solid 14-8 for the Royals in 1972 with an ERA of 2.08 but Spider pitched just 54 innings for the ’73 Reds as he was hindered by injuries. He pitched only another 85 innings the next year. Spider was a good pitcher when he was healthy– he just wasn’t ever healthy, at least during his sojourn with the Reds.

Jim Kern

Reds GM Dick Wagner traded George Foster to the Mets for Kern, Greg Harris and catcher Alex Trevino after the 1981 season. Kern was a three-time All-Star with the Texas Rangers and finished 4th in the Cy Young voting in 1979 as a reliever. Injuries and overwork slowed him down but Kern had a solid second half of the 1981 season and Wagner took a gamble. Kern, a 6’5” righthanded flamethrower, was famous for his fastball and intimidating whiskers. In 1982, the Reds had a ban on facial hair. When Kern reported for spring training, he was clean shaven and gave a bag of his shaved whiskers to pitching coach Bill Fischer. It went downhill from there, Kern was effective but no longer an elite pitcher. The 1982 season was a disaster for the Reds, resulting in the first 100-loss year in Cincinnati history. Kern feuded with management, especially Chief Bender, the Reds Vice President for Player Development. Kern demanded a trade and started to grow a beard when Bender said that Kern, Johnny Bench and Cesar Cedeno were the reasons for the Reds dismal year. “When you’re 30-some games under the .500 mark,” said Kern, “it has to be a community effort. You can’t pinpoint three guys and blame them.” Kern had a valid point. Every trade Wagner made before the 1982 season was a flop, from Clint Hurdle to Trevino to Cedeno. Players promoted from AAA were disappointing, including Paul Householder and Duane Walker. The 33-year old Kern was traded to the White Sox for the “proverbial player to be named later” on August 23, 1982. His line with the Reds— a won-loss record of 3-5, 2 saves, 76 innings pitched, 61 hits, 43 strikeouts, 48 walks and WHIP of 1.434. Harris, the other pitcher acquired by Wagner in this trade, was worse– 2-6 and a 4.03 ERA that season. Trevino was a mediocre catcher and a dreadful hitter.

Jimmy Haynes

Here is another free agent acquisition by the Reds, first in 2002 and again one year later after his only decent season in Cincinnati.. In many ways, Haynes reflects the Reds of the early part of that decade — good hitting and not a lot of pitching. Haynes was another control specialist with underwhelming stuff but he averaged 190 innings of work over the previous six seasons before arriving in Cincinnati. Haynes pitched three years for the Reds and had one good season, in 2002, when he was 15-10 and posted a 4.51 ERA. He pitched 196 innings that year but yielded 221 hits. But by “good” it refers to Reds standards. The Reds Opening Day starter in 2002 was Joey Hamilton (4-10, 5.27 ERA in ’82) — not exactly Soto, Cueto or Seaver. In 2003 (the first game ever at Great American Ballpark) the Opening Day starter was Jimmy Haynes. That season, Haynes was 2-12 with an awful ERA of 6.30. The Reds signed him to a $2.5 million deal originally, certainly not Milton-esque and they did get one decent season out of him. But unfortunately, Jimmy Haynes reflected the Dunn-Griffey Era of patchwork pitching staffs and other similar pitchers in that that time frame such as Josh Fogg, Elmer Dessens and Chris Reitsma.