Anthopoulos only said it wasn't the right "fit," leaving much to the imagination. But the reality is, he didn't feel he'd be able to work comfortably with Shapiro, according to people familiar with the situation.
There's been a suggestion Anthopulos envisioned a much more hands-on approach for Shapiro than outgoing president Paul Beeston and wasn't comfortable with an extra layer above him. But while there may be something to that, that doesn't really sound like the crux of the issue.
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No, this was about the match. The pair is said to have had only a couple big meetings and a few more phone calls while Shapiro was finishing out his stay in Cleveland and giving Beeston his space. But word is, while Shapiro thought the confabs went well, Anthopoulos saw them negatively. While Shapiro thought he was being effusive in his praise, Anthopoulos heard only criticisms.
Shapiro apparently thought he was providing sufficient support. But after working 24-hour days for months, Anthopoulos, undoubtedly fried, probably needed some pats on the back. A friend of his outside the organization suggested he felt was being constantly told he's no good.
Shapiro, a brilliant man who normally chooses his words precisely, at one point was said to have discussed the lack of top prospects at the upper levels and the need to replenish the coffers following the big, season-altering trades, and Anthopoulos apparently took that as a slap. Shapiro and Anthopoulos both declined to talk for this article, but one other person familiar with the situation said he understood why Anthopoulos felt the way he did; that person said he believed Shapiro wasn't especially complimentary, especially considering the wonderful run the Blue Jays were on.
Perhaps Shapiro thought he was being pro-active in discussing the issues the club faced going forward. However, his remarks were received as unnecessary criticism. Another person with Blue Jays connections suggested that the erudite, Princeton-educated Shapiro, perhaps unintentionally, came off as smug, especially considering the Indians have had very solid, though not always spectacular, results in a very small market, and a less-than-stellar overall farm record (they made their hay with some very good trades). One other Jays person remarked, regarding Shapiro, "I didn't see his rings. Maybe they didn't get past the border."