Top NYY Could-Have-Beens: Ted Lilly

Jeff Weaver takes his place among the ranks of Carl Pavano and Kei Igawa in the annals of recent Yankees infamy.

In his lone full season in pinstripes, the lanky right-hander posted a 5.99 ERA in 159.1 innings, surrendering a walk-off home run in Game 4 of that years World Series for good measure.

Along the way, he was criticized by his manager, Joe Torre, for his antics and body language on the mound and controversy often seemed to find him.

It was pretty much the textbook definition of an unmitigated disaster.

And he cost the Yankees a damn good pitcher named Ted Lilly.

Years in Yankees Organization: 2000-02 How They Left: Traded to Athletics in July 2002 Career MLB Yankees Statistics: 8-12, 32 GS, 205.1 innings pitched, 4.65 ERA, 97 ERA+, 2.2 bWAR Career MLB Statistics: 15 seasons, 331 GS, 130-113, 1,982.2 innings pitched, 4.14 ERA, 106 ERA+, 27.1 bWAR Theodore Roosevelt Lilly III grew up in Oakhurst, California, a quiet town just 14 miles from Yosemite National Park.

Undrafted out of Yosemite High School, the southpaw showed enough at Fresno City College to warrant selection by the Dodgers in the 23rd round of the 1996 MLB Draft .

Expectations were low for Lilly when he reported to Yakima, Washington that same year to pitch for the short-season Bears, whose general manager later said the undersized hurler looked more like the grocery store bag boy than a professional pitcher.

In eight starts with Yakima, the 20-year-old went 4-0 with a short-season-leading 0.84 ERA, helping pitch the Bears to a league championship.

That was the guy we wanted to have the ball, said Joe Vavra, who earned league Manager of the Year honors helming the Bears that season.

He looked like a little kid out there, but he was all business.

Lilly continued to impress at Class-A San Bernadino the next season, posting a 2.81 ERA while striking out 158 in 134.2 innings and taking home Advanced California League Pitcher of the Year honors.

He pitched well enough in the 1998 season at Double-A San Antonio to earn a promotion to Triple-A, a remarkably swift ascent for a player who was pitching at a junior college just two years earlier.

With his stock on the rise, Lilly was dealt that offseason for the first of five times in his career.

In a seven-player deal that netted the Dodgers All-Star shortstop Mark Grudzielanek, the team shipped the 22-year-old southpaw to the Montreal Expos.

After finishing out the season with their Triple-A affiliate, Lilly was named the 66th-best prospect in baseball by Baseball America before the 1999 season.

After beginning the season at Triple-A, Lilly got the call to the big leagues in May.

He struggled mightily in two stints for the Expos that year, allowing a 7.61 ERA in 23.2 innings.

Perhaps due in part to that ignominious debut, Montreal included Lilly as a player to be named later that offseason in a deal that also sent Jake Westbrook to the Yankees for Hideki Irabu (thus making him part of the transaction tree that led to New York drafting Aaron Judge).

Lilly has the distinction, alongside the likes of David Ortiz and Trea Turner, as being one of just 14 players included in trades as players to be named later to make an All-Star team.

He spent most of the 2000 season at Triple-A Columbus, where he once again put in a commendable showing, this time with a 4.19 ERA across 22 starts (137.1 innings), which was better than league-average.

He was a good, hard worker, he knew what he wanted to pitch at the highest level, said Clippers manager Trey Hillman said, who won International League Manager of the Year honors in 2000.

But, once again, he struggled in limited opportunities at that highest level, posting a 5.63 ERA in seven bullpen appearances with the eventual champion Yankees that season.

The following campaign would offer Lilly his first extended opportunity with the Yankees, as manager Joe Torre cycled through a few different options in search for a quality back-of-the-rotation arm.

The results were disappointing, even in a high-offense era; in 26 appearances (including 21 starts) in 2001, Lilly posted a 5.37 ERA and was left off the playoff roster for the eventual pennant-winners.

That made 2002 something of a make-or-break campaign for the 26-year-old former prospect.

Despite a crowded crop of Yankees starters, Lilly worked his way into the rotation and began to put it together, posting a 3.40 ERA and 1.057 WHIP in 76.2 innings through July 5th.

The southpaw began to flash excellence, no-hitting the recently-record-breaking Mariners for 7.1 innings on April 28th until a Desi Relaford single broke it up.

The offense let him down in that one and New York lost, 1-0, despite Lillys one-hit effort, but he got to be a 1-0 winner in a three-hit, 11-K gem on June 22nd in San Diego.

After one more Lilly start, Brian Cashman would make one of the least successful swaps of his tenure as Yankees GM.

In a three-team deal that netted the Tigers Jeremy Bonderman and Carlos Pena, the Yankees moved Lilly to the Athletics while acquiring Detroits Jeff Weaver.

While Weaver sputtered in pinstripes, Lilly proved a sturdy, if unspectacular, cog in the Moneyball machine behind their trio of aces.

In a season and change in Oakland, the left-hander went 14-11 with a 4.37 ERA and 102 ERA+, establishing himself as a legitimate MLB starter.

His tenure with the Athletics concluded when they were defeated by Boston in the 2003 ALDS despite Lilly throwing nine innings across two appearances without permitting an earned run.

Remarkably, Lilly was traded yet again before the 2004 season, this time heading to Toronto in exchange for outfielder Bobby Kielty.

Still just 28, Lilly was now on his fourth franchise.

Despite this tumult, he broke out in his first year with the Blue Jays, making his first All-Star team while going 12-10 with a 4.06 ERA and 119 ERA+.

After two more up-and-down seasons in Toronto (and some feuding with manager John Gibbons), the pitcher who had been passed around like a hot potato reached free agency.

Finally able to chart his own course, Lilly reportedly narrowed his search to two suitors: the Cubs and the Yankees.

But the Yankees punted on the potential reunion, informing Lilly they instead intended to bring a different left-handed ex-pat back into the fold: Andy Pettitte.

Lilly signed a four-year, $40 million deal with the Cubs, and it was in Chicago where he would find his greatest success.

In parts of four seasons with the North Siders, the veteran posted a 3.70 ERA and 122 ERA+, striking out 598 while walking only 184.

Lillys 3.25 strikeout-to-walk ratio as a Cub still ranks seventh in franchise history among pitchers with at least 500 innings pitched.

Along the way, he helped Chicago win consecutive NL Central crowns (albeit while suffering glove-spiking playoff heartbreak) in 2007 and 2008, then picked up his second All-Star berth in 2009.

In what proved to be a career year, the 33-year-old posted a 3.10 ERA and 144 ERA+, registering 5.0 bWAR in just 27 starts while picking up his 100th career victory.

He also hit a pretty hilarious bumbling, stumbling triple in Houston that year (if youre into that kind of thing).

Given this is Ted Lilly were talking about, it should come as no surprise that he was traded midway through the next season (not long after another no-hit bid ), this time to the Dodgers for a mostly forgettable return.

He pitched well enough down the stretch to earn a new three-year, $30 million deal to stick with LA.

That deal ended in disappointment, as a middling first full season with his original team was followed by two injury-marred ones, with Lilly starting 13 games between 2012 and 2013.

He was designated for assignment in July of 2013 and appeared on the verge of signing a minor-league deal with the rival Giants until they announced that upon reviewing Ted Lillys medical history we are going to hold off on pursuing a minor-league contract right now.

Beset by injuries, those words were the death knell of Lillys career.

He announced his retirement that November.

In a career that spanned 15 seasons and six teams, Lilly was a picture of reliability.

At worst, he was a capable innings-eater.

At best, he was an All-Star.

As the Yankees cycled through an array of over-the-hill starters (Kevin Brown, Randy Johnson, Jaret Wright, the 2007 version of Roger Clemens) and talented pitchers who never lived up to their potential (Weaver, Pavano, Igawa, Jose Contreras) in the seasons after Lillys departure, they certainly could have used a pitcher of his caliber.

Previously on Top Could-Have-Been Yankees Drew Henson Full List (to date).

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