The Cubs had hoped to contend with the signing of Andre Dawson in 1987. They did for a while, but collapsed in September. Former manager Jim Frey, now GM, attempted to make that right in ‘88. He made some... interesting (translation: mostly not good) deals.
February 12: Acquired Rich Gossage and Ray Hayward from the Padres for Keith Moreland and Mike Brumley
Well. This swap was necessitated by the trade the previous December which sent closer Lee Smith away. The Cubs thus needed a closer, and turned to Gossage, who had done that job very well for a decade for the White Sox, Yankees and Padres, including in ‘84 in the NLCS against the Cubs.
Gossage was 36 at the time of the deal and had been in decline for a couple of years, and it showed in Chicago. He had four blown saves by early June and nine overall and for me, a personal anecdote sums him up. I met him briefly at an autograph session that summer. He looked as if he’d rather have been any place on Earth than doing that. He just seemed to not like being a Cub at all.
The Cubs actually appeared to be ready to keep him in ‘89, but released him at the end of Spring Training. An itinerant the rest of his career, he pitched for the Giants, Yankees, Rangers, A’s and Mariners for the next few years, then retired. He posted -0.2 bWAR for the Cubs, and when you hear from him in recent times, he’s always complaining about how the game isn’t as good as it was when he played.
One of my least favorite Cubs ever.
Moreland had -1.2 bWAR for the Padres, so I guess the Cubs “won” this deal. Hayward never pitched for the Cubs and was traded away before the season started.
March 17: Acquired Dave Meier and Greg Tabor from the Rangers for Ray Hayward
This gets my nomination for most “Who are those guys?” trade in Cubs history. Hayward pitched in 12 games for the Rangers and was done. Meier spent the entire 1988 season at Triple-A Iowa, where he hit .305/.358/.509 with 20 home runs. That got him a September callup in which he went 2-for-5. Tabor also played 1988 at Iowa, then was done.
March 31: Acquired Mike Bielecki from the Pirates for Mike Curtis
Here’s a deal that worked out very well, for a while, anyway. Bielecki spent most of ‘88 at Iowa, where he didn’t pitch much, and when he did, it was mostly in relief (23 games, only three starts). He made 19 appearances for the Cubs that year (five starts) without distinction (0.4 bWAR).
Then he exploded on the scene in 1989 as a key part of the Cubs rotation, posting 18 wins and a 3.14 ERA, 4.3 bWAR and ninth place in Cy Young voting. He was 29 and it looked like he could be a good rotation starter for the Cubs for a few years.
His next two years were decent, but not quite as good as ‘89, and the Cubs wound up trading him away in a deal we’ll cover later.
Still, as Curtis never played in the major leagues, this was a big win for the Cubs.
April 1: Acquired Bill Landrum from the Reds for Luis Quinones
Landrum missed a lot of time with a knee injury and he pitched in just nine games at Triple-A Iowa and seven for the Cubs. In the majors he posted a 5.84 ERA and 1.784 WHIP. He left as a free agent after the season and signed with the Pirates, where he had three good years as a closer (56 saves, 2.32 ERA) and appeared in the postseason in both 1990 and 1991. That would have looked pretty good in the Cubs bullpen in those years.
Quinones posted 1.8 bWAR in four years with the Reds. This was a minor deal that turned out better for Cincinnati.
May 19: Acquired Pat Perry from the Reds for Leon Durham
Durham was another guy who looked like he could have a long Cubs career. But drug use got the better of him and the Cubs shipped him away. He played only 21 games for the Reds before going into drug rehab, and played a handful of games for the Cardinals in ‘89 before he was suspended for violating the Commissioner’s drug policy, and retired.
Durham did eventually rehab and became a longtime, well-respected hitting coach at Triple-A Toledo in the Tigers organization. He spent 17 years there, one year as the MLB hitting coach in Detroit and then two years as the Reds’ Triple-A hitting coach.
Perry was nothing special, a journeyman lefthanded reliever, but he had two decent years in the Cubs bullpen in 1988 and 1989, posting 1.7 bWAR total.
July 14: Acquired Mitch Webster from the Expos for Dave Martinez
How do I put this? Well... I guess I just have to put it out there. There have long been rumors, never substantiated, that Martinez was having an affair with Ryne Sandberg’s first wife Cindy, and that’s what forced this trade.
We’ll never know for sure.
What I do know is that Martinez was just 23 and it looked like he might be coming into his own with the Cubs at the time of the deal. He had a 2.7 bWAR year in ‘87, though his numbers in ‘88 had declined a bit.
Webster was 29, and apart from two 30+ steal seasons, had never been anything special with the Blue Jays and Expos. It was clear Martinez had more potential, plus he was a better defender.
In two years in Chicago, Webster batted .261/.325/.381 in 154 games, with seven home runs and 24 stolen bases, posting 2.5 bWAR. He was traded to Cleveland after ‘89 and we’ll cover that later. He played through 1995.
Martinez played four years in Montreal and batted .279/.324/.401 with 23 home runs and 68 stolen bases, good for 6.4 bWAR. The Expos got the better of this deal, though not by much.
But Martinez played 10 more seasons after he left Montreal (16 seasons total) and had 1,599 career hits and a total of 19.2 bWAR. He was a better player than Webster (14.4 bWAR over 13 total years). As you know, he then became a respected bench coach and manager, earning a World Series ring with the Cubs in 2016 and another in Washington in 2019.
Martinez played for nine teams overall, so he can be a popular choice in Immaculate Grid.
September 29: Acquired Kevin Blankenship and Kevin Coffman from the Braves for Jody Davis
This was one very odd deal. There were literally three days remaining in the season when this trade was made. Why do it then and not in the offseason?
Davis, whose numbers had declined from his prime with the Cubs in the early ‘80s, actually suited up for those last three games with the Braves and played in two of them. He was a Braves backup catcher in ‘89, played 12 games for them in ‘90, then retired. Total bWAR in Atlanta: -1.3.
The two Kevins combined to pitch a total of 14 games for the Cubs (five starts). Total bWAR between the two of them for the Cubs: -1.1.
Cubs win! Cubs win! By 0.2 bWAR.
December 5: Acquired Mitch Williams, Curtis Wilkerson, Steve Wilson, Paul Kilgus, Luis Benitez and Pablo Delgado from the Rangers for Rafael Palmeiro, Jamie Moyer and Drew Hall
Oh, man, yet again.
As was the case with Martinez, there were rumors about Palmeiro and Cindy Sandberg, again, never substantiated.
There was talent in this deal coming to the Cubs. Wilson, in particular, was a very good prospect, but had little success in three Cubs seasons (total 1.3 bWAR). Kilgus was the Cubs’ more-or-less fifth starter in ‘89, then was traded. Wilkerson was a good-field, no-hit infielder for the Cubs for two years.
Hall, who was the Cubs’ No. 1 pick in 1984 (third overall), pitched briefly for the Rangers in 1989 and the Expos in 1990 and then was done. Better players taken in that first round after Hall: Jay Bell, Mark McGwire, Shane Mack, Oddibe McDowell, Terry Mulholland and Norm Charlton.
The centerpiece was Williams, who, as you surely know, threw really hard but rarely knew where the ball was going. Famously, on Opening Day he struck out the side after the bases were loaded with nobody out on three singles. This went on all year — Williams walked 52 of the 365 batters he faced (14 percent), yet posted 36 saves, though with 11 blown saves. The Cubs probably don’t win the N.L. East that year without him.
And he gave everyone at Wrigley a huge laugh when he hit a three-run homer against the Mets in September for his first MLB hit. Full story here, but here’s the homer (pardon the video quality):
On the other hand, Palmeiro went on to a long career in Texas and Baltimore, recording 3,020 hits and 569 home runs before becoming a pariah in baseball for steroid use. The thing is, either Palmeiro or Mark Grace was going to be traded after the ‘88 season. Palmeiro had played left field and was terrible at it (he played just one game in the outfield the entire rest of his career after leaving Chicago); he could really only play first base and so it was him or Grace. The Cubs chose Grace.
As for Moyer, he’d had a pretty good year in ‘88 but... well, the Cubs chose Kilgus and Wilson instead.
If you’re not familiar with this story, or even if you are, it bears repeating here. Moyer had two mediocre years in Texas and one bad one in St. Louis in ‘91 and the Cardinals released him. The Cubs signed him to a minor league deal before Spring Training in 1992. The Cubs were going to release him after camp, as he hadn’t thrown well, and offered him a minor league coaching job. He told then-GM Larry Himes, “I think I can still pitch,” and turned down the offer.
It took him another year for him to get back to the majors with the Orioles, but Moyer pitched 19 MLB seasons after that release by the Cubs, finishing in the top six of Cy Young voting three times and being a key part of the Phillies rotation in their World Series winning year of 2008. Moyer’s a borderline Hall of Famer. They should have kept him, both times they let him go.
This was a terrible deal for the Cubs, who got a little value from Williams (2.3 bWAR) and negative bWAR from Kilgus and Wilkerson. Meanwhile, Palmeiro had a 71.9 bWAR career, first with the Rangers, then the Orioles, then back to Texas. Moyer posted 45.9 bWAR after that conversation with Himes.
That’s about as lopsided as trades get.
December 8: Acquired Lloyd McClendon from the Reds for Rolando Roomes
Roomes was an interesting guy, one of five MLB players born in Jamaica (though he grew up and played high school baseball in New York). He went just 3-for-16 as a Cub. He had one decent year as a backup outfielder in Cincinnati.
McClendon had a very good year for the Cubs in ‘89, batting .286/.368/.479 in 92 games and seeing time at catcher, first base, third base and left field. They had gotten off to a good start, then lost five in a row in early May and scored only seven runs in the five games.
McClendon came to bat in the second inning of a game against the Braves at Wrigley Field May 15 and smacked a three-run homer that seemed to energize the entire team. They’d win five straight and 15 of 20 and roared into first place in the N.L. East.
The next year was not as kind to McClendon and, batting just .159 in early September, he was traded to the Pirates. Eventually, he became the manager in Pittsburgh from 2001-05 and also managed briefly in Seattle and Detroit.
Overall, I’ve got to give the ‘88 trades a D-. Only the Bielecki acquisition was really good and some of the others gave up real talent and got little in return.
Give the Cubs a grade for their 1988 trades.
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