When will the Yankees regret the Jacoby Ellsbury contract?

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These huge, later-career deals never turn out great. The best you can hope for when you sign a 30-something baseball player to a hugely expensive long-term deal is that he will have a couple of good years on the front end to boost up his value, have a nice rebound year somewhere in the middle, and not be utterly useless and difficult to deal with at the end.

You can go down the list of players signed longterm after the age of 30 – Alex Rodriguez, Albert Pujols, Adrian Gonzalez, Josh Hamilton, Alfonso Soriano, Vernon Wells, Ryan Howard, Jason Giambi, Ken Griffey Jr., Mike Piazza, on and on — and you will find, over and over, deals that teams regretted t some point or other.

So the Yankees will inevitably regret signing Jacoby Ellsbury to a seven-year, $153 million deal — the real question is when. If they don’t regret the deal until 2018 or 2019 — when Ellsbury is a 35-year old coming to the end of his deal, struggling to stay in center field, constantly battling some nagging injuries — then you would have to say that they should feel pretty good about things. The trouble with these deals is that the regret often happens much earlier than you expect. I’m sure the Angels KNEW they were going to regret the Josh Hamilton deal at some point. I just don’t think they expected it to be the first year.

Ellsbury, when healthy, is a fabulous baseball player. I’ve seen him compared pretty often with Carl Crawford, and Crawford was pretty great as a young player. But I think Ellsbury is an even better player than Crawford was in Tampa Bay. For one thing, he plays centerfield while Crawford played left. They were both superior defenders, but a superb center fielder is quite a bit more valuable than a superb left fielder. Ellsbury also gets on base more and might even be a more potent base stealer (last year, Ellsbury stole 52 bases and was caught just four times all year — Crawford led the league in steals annually but would get thrown out a bit more).

Also, Crawford never had a season like Ellsbury’s 2011, when he hit .321/.376/.552 with 32 homers, 105 runs scored, 119 RBIs and 39 stolen bases (though that year he was caught a lot — 15 times).

Then again Crawford was also much more durable than Ellsbury. From 2003 to 2010, Crawford played 140-plus games every year but one, and even in the year he was hampered by injuries he played 109 games. Ellsbury meanwhile has had two of the last four seasons destroyed by injuries — he played just 18 games in 2010, just 74 games in 2012. Nobody can say if those injuries project anything for the future but they are part of his history.

The Yankees have so much money — and so much money on the line — they figure he’s worth the risk. I can see their point. If the Royals or Mariners or Brewers or some team like that had given Jacoby Ellsbury a seven-year, $153 million deal, you could say without any hesitation that they had lost their minds. That’s exactly the sort of deal that can paralyze a smaller franchise for a half-decade.

But the Yankees are a different category. The Yankees in that too-big-to-fail category — they have money on top of money, and they are constantly aware that if they put a losing and uninteresting team on the field, everything crashes. Nobody buys their absurdly high-priced tickets. Fewer people watch their cash cow Yes Network. The back page of the Post and Daily News looks elsewhere. The Yankees brand — the most lucrative in America — starts to devalue a little bit and then a little bit more and … they just can’t let that happen. Money, they have. Wins, they need.

And so the Yankees are playing a different game. If they get even one superstar year and maybe a couple of good years from Ellsbury, they will probably be pretty happy.

How good a bet is Ellsbury to have one more season like he did in 2011? I’m not sure. That was an unusual power surge from a player who has never hit double-digit homers any other year. Then again, that’s a very short porch in right field at New Yankee Stadium.

Truth is, we can spend a lot of time trying to compare Ellsbury to other players — his Baseball Reference comps of Phil Bradley, Tony Gonzalez and Roberto Kelly do not strike an encouraging note — but it’s hard to find many players like Ellsbury in baseball history. He stole 70 bases in a season. He hit 30 home runs in a season. There’s only one other player in baseball history who pulled off those two feats in a career, Eric Davis. And he had a rebirth in his mid-30s, even while battling colon cancer.

My gut instinct is that it will work out for the Yankees. But I say this in part because things always seem to work out for the Yankees.

I can say this with more confidence: If the Mariners sign Robinson Cano … that won’t work out.

This Day in Transaction History: Phillies acquire John Kruk from Padres

John Kruk
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John Kruk is one of the more underrated hitters in baseball history. Kruk, who is currently a broadcaster for the Phillies, had a 10-year career during which he hit exactly 100 homers, batted exactly .300, and posted an excellent .397 on-base percentage. In baseball history, there are only 32 members of the admittedly arbitrary 100/.300/.395+ club. Kruk is one of only 10 members of the club that played after 1963. The others: Mike Trout, Joey Votto, Todd Helton, Chipper Jones, Manny Ramírez, Frank Thomas, Larry Walker, Edgar Martinez, and Wade Boggs. Of them, five are Hall of Famers. Trout and Votto will be, and Helton and Ramírez should be.

On this day in 1989, the Phillies made a franchise-altering trade, acquiring Kruk along with infielder Randy Ready from the Padres in exchange for outfielder Chris James. The Padres had just swept the Phillies at home and were hoping to jump into the playoff race. They immediately went into a losing skid, but caught fire at the end of the season, finishing 89-73. However, that wasn’t good enough as the Giants won the NL West with a 92-70 record. James was solid for the Padres, posting a .743 OPS with 11 homers and 46 RBI in 87 games.

Kruk had an interesting but brief major league career with the Padres. His roommate, Roy Plummer, was an armed robber. Kruk was completely unaware of this. In spring training of 1988, the FBI informed Kruk of his roommates’ activities. Kruk feared retribution from Plummer and said that the anxiety affected his baseball performance. In 1988, Kruk batted what was for him a poor .241/.369/.362 with nine homers and 44 RBI over 466 plate appearances.

The Phillies didn’t enjoy immediate success upon Kruk’s arrival in 1989. The club finished the season with a losing record and would do the same in the ensuing three seasons. None of it was Kruk’s fault, though: in aggregate, from 1990-92, he hit .303/.393/.459, earning two All-Star nominations. In this span of time, the only other first basemen to hit above .300 were Frank Thomas, Paul Molitor, Hal Morris, and Rafael Palmeiro. The Padres had used Kruk both in the corner outfield and at first base, but the Phillies made him a full-time first baseman, which turned out to be a good move.

In 1993, everything came together for the Phillies and Kruk had what was arguably the greatest season of his career. He hit .316, which was actually seven points below his average the previous year, but he drew 111 walks to push his on-base percentage up to .430. Kruk hit third in the lineup, creating plenty of RBI opportunities for Dave Hollins in the clean-up spot, Darren Daulton at No. 5, and the trio of Jim Eisenreich, Pete Incaviglia, and Wes Chamberlain in the No. 6 spot. The Phillies shocked the world in ’93, winning the NL East by three games over the Expos with a 97-65 record. They then dispatched the Braves in six games in the NLCS to advance to the World Series against the Blue Jays.

Kruk was productive in the NLCS, contributing six hits including a pair of doubles, a triple, a home run, four walks, five RBI, and four runs scored. But he turned things up a notch in the World Series, registering multi-hit performances in the first three games. He would finish the World Series with eight hits in 23 at-bats along with seven walks, four RBI, and four runs scored. The World Series was winnable for the Phillies as they lost a barnburner Game 4 15-14, and of course, dropped the deciding Game 6 on a World Series-clinching walk-off three-run home run by Joe Carter off of Mitch Williams.

1994 was tough on Kruk in many ways. He was diagnosed with testicular cancer in spring training. Knee issues continued to bother him, and then Major League Baseball had a work stoppage. In an abbreviated season, Kruk hit a still-productive .823 OPS. He became a free agent and, when baseball came back, he signed with the White Sox. In the first inning of a July 30 game against the Orioles in ’95, Kruk singled to left field off of Scott Erickson. He reached first base, bowed to the fans, and walked off the field into retirement. Kruk told the media, “The desire to compete at this level is gone. When that happens, it’s time to go.”

Kruk has spent his post-playing days working in sports media as both a broadcaster (Phillies, ESPN nationally) and as a commentator (The Best Damn Sports Show Period, Baseball Tonight). The Phillies inducted him into their Wall of Fame in August 2011. One wonders if Kruk hadn’t been bit by the injury bug, and if there hadn’t been a work stoppage, if he might have been able to accrue some more numbers to have a borderline Hall of Fame case. Regardless, he’ll go down as one of the games’ quietly great hitters.