Four Years Later: Halladay/Lee Day

Four years ago today – December 16, 2009 – the Phillies made one of the strangest pairs of deals in club history when they acquired Roy Halladay from the Toronto Blue Jays, and subsequently dealt Cliff Lee to the Seattle Mariners.

The Halladay deal was immediately celebrated as the great acquisition it was: bringing in one of the absolute best pitchers in the game (and then getting him to sign a three-year, $60 million extension that was probably below market value) for three highly-regarded prospects. Travis d’Arnaud, Kyle Drabek and Michael Taylor, ranked by Baseball America as the seventh-, fifth- and sixth-best prospects in the organization prior to the 2009 season, and fourth-, second- and third- best that November, following the trade to acquire Lee midseason. The only one of the three with more optimism than pessimism remaining surrounding his big league future is d’Arnaud.

Lee, in a stunning move, was then flipped out to Seattle for a package of prospects that was underwhelming then and looks downright pathetic now. Lee was under contract for just $9 million in 2010, a club option that was a bargain following a Cy Young Award-winning campaign for Cleveland in 2008 and a strong follow-up between the Indians and Phillies in ’09. The ESPN wire story at the time quoted Amaro’s rationale behind dealing Lee after acquiring Halladay as follows:

“If I had my druthers, I’d love to have both of them on the club,” Phillies general manager Ruben Amaro Jr. said.

Amaro said he didn’t keep Lee, who has one year and $9 million remaining on his contract, for two reasons. He felt Lee wanted to test the free-agent market next winter and couldn’t afford to keep him and lose him for nothing. And he needed prospects to replenish the ones lost in both the Lee-from-Cleveland trade and the Halladay deal.

“I had a little discomfort that we’d be able to do the type of deal that I’d feel comfortable with,” Amaro said.

Apparently, whether it was Amaro whose comfort level changed or ownership’s, Lee was brought back the following winter on a five-year, $120 million free agent deal. Of the prospects acquired from Seattle for Lee – Phillippe Aumont, Tyson Gillies and J.C. Ramirez – little optimism remains. Aumont has flashed excellent stuff, but command problems and clashes with coaches and management have his future in doubt; Gillies has dealt with numerous injuries and had a fairly serious brush with the law (charges later dropped), and his hold on a 40-man roster spot is tenuous; Ramirez was not retained this winter and has signed with the Indians, contributing little while he was around.

Two fascinating deals, separate yet corresponding, helped set the tone for most of Ruben Amaro’s tenure to date: a mix of confusion and excitement, and a lingering sense of never knowing just what’s coming next.

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  1. hk

    December 16, 2013 04:41 PM

    It was the best of times…it was the worst of times.

  2. Dante

    December 16, 2013 05:32 PM

    So Amaro was worried he’d lose him for nothing – except the Type A FA compensation he’d get when Lee declined an arbitration offer.

  3. Bob

    December 16, 2013 06:42 PM

    The Cliff Lee trade was a debacle and set this team back. Gillies was supposed to be our CF of the future and Aumont was our closer in waiting. Two areas where we needed big time help last year were CF and RP. Instead, both of these players can’t seem to stick. You can’t – you just can’t – blow that trade and get nothing in return.

  4. Kevin

    December 16, 2013 07:52 PM

    Sadly, I can understand the rationale that went into these moves. And maybe it wouldn’t look so bad if the Phillies had been able to get talent that panned out.

    Hey, when was the last time the Phillies traded for talent that actually did pan out?

  5. NJG

    December 16, 2013 10:23 PM

    A severe case of RAJ not having a comprehensive plan. He tried to get Halladay at the deadline, but could not pry him from the Jays, so he went after Lee in a downright robbery from the Indians.

    2009 offseason starts with a 3 year / $18 mil deal for Polanco, followed by this deal, which I think most agree was a way to keep costs down. This, of course, proved ludicrous when RAJ signed Lee at the end of 2010 for the discounted cost of $120 million. Also, don’t forget that the Jays kicked in $6 million of Halladay’s salary. Amaro could have had Halladay and Lee in 2010 for approximately $18 million combined, which probably negates the need trade for Oswalt, keeping Gose and Villar…

    What makes this even more frustrating is that RAJ then signs Blanton to a 3 yr/ $24 million deal 35 days later (We’ll leave out the Howard extension three months later).

    Do I sound bitter?

  6. SteveH

    December 17, 2013 09:50 AM

    Let’s be honest with ourselves, this move was really the beginning of the end. Who in their right mind thought trading for one stud means you have to trade away another one. The only way you make the Lee trade is if one of the pieces back is a can’t miss stud starter and I do not believe Aumont was ever considered to be that. Just think of what might’ve been, maybe another World Series, but probably not.

  7. Ryan

    December 17, 2013 09:57 AM

    I think that it’s certainly worth noting that none of the top prospects sent to Toronto for Halladay has turned into anything yet–and only D’Arnaud even has a chance to turn into anything. None is a slam dunk at this point let alone a future star. The Lee prospects haven’t done much either, but it’s not looking good. In a vacuum, it’s certainly possible that RAJ traded one year of Lee (at a very good price) for four of Halladay (at a good price) which isn’t such a bad trade considering that Doc was the better pitcher the first two years he was here.

    Re-signing Lee the next offseason was a coup. Perhaps sending him to Seattle helped him realize what he was missing in Philly and helped with re-signing him.

    You can’t always look at these things and be as negative as possible. This deal set the groundwork to get Lee and Halladay on the same team for two healthy seasons albeit in a roundabout way. This is inching closer to being a GOOD trade so long as D’Arnaud doesn’t amount to much.

  8. Bob

    December 17, 2013 10:57 AM

    Ryan, d’Arnaud would be our starting catcher this year. Instead, we had to invest 24mm in Chooch this year. I’m not saying the Phils shouldn’t have made the deal for Doc – I would’ve made that trade in a heartbeat. But, to be a competent GM, RAJ needs to get back at least one player from the Lee deal who can help the team in the vein of d’Arnaud. That’s his job. You can’t trade a cost-controlled Lee and whiff on every prospect you get back.

    The only reason that Lee came back is that the sellout streak kept going and, concomitantly, the revenue stream. Each year, Phils ownership probably says that it wants to take home X% of profit and the remainder can be reinvested in the team. With the revenue of selling out every game and the peripherals that go along with that, the Phils ownership felt more comfortable that it could maintain – if not increase – their profit and increase investments in player procurement.

  9. yo

    December 17, 2013 12:24 PM

    Ryan: if you ignore the whole 2010 playoff thing

  10. Mike B.

    December 17, 2013 01:19 PM

    Yeah, it would have been nice to roll Cliff out as well in that series against the Giants.

  11. Ryan

    December 17, 2013 02:06 PM


    D’Arnaud might be our starting catcher. Might. He’s likely to become a good major league player, but that isn’t a certainty by any means. He did pretty terribly in his first call up this past season, has some injury issues (which is very bad for a catcher), and hasn’t played more than 67 games in a season over the last two years. He’s FAR from a sure thing. Would I love to have him the Phils’ system or to be able to split time with Ruiz? Sure, but I would by no means ordain him as the next Trout or Harper–or even a definite to become a big league regular.


    If you ignore the 2010 playoff thing? Huh? Make more sense please.

  12. Bob

    December 17, 2013 02:26 PM

    Ryan, if d’Arnaud is with the Phils, do you resign Carlos Ruiz for three years and 24 mm?

  13. yo

    December 17, 2013 02:36 PM

    Ryan, your support of a defenseless trade ignores the fact that the trade left the Phils without Lee for the 2010 playoffs.

    Does that make more sense?

  14. KH

    December 17, 2013 03:14 PM

    The signing of Cliff Lee as a free agent was the best move Amaro has made as GM. Too bad it was only needed because of his worst trade sending Lee to Seattle for a pupu platter of prospects.

  15. Phillyguy

    December 19, 2013 07:40 PM

    Gillick always preached listening to the guys you hire in the scouting department and RAJ apparently listening. He relied on Benny Looper who had been in player development with Seattle and had scouted and drafted the players the Phillies got for Lee. It seems to be pretty common for GM’s and other front office members to over value their picks. Ed Wade traded for ex-Phillies when with Houston, Dallas Green for ex-Phillies in Chicago (Sandberg the most notable) and Gillick with Werth, Dobbs, Moyer, etc. The players that Looper thought were good were already underachievers and were down the Mariners prospects list.

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